Subject of bioorganic chemistry.
Structure and isomerism of organic
connections.
Chemical bond and interaction
atoms in organic compounds.
Types of chemical reactions.
Poly- and heterofunctional
connections.
Basic textbook – Tyukavkina N.A., Baukov Yu.I.
Bioorganic chemistry.
Text of lectures and manual “Bioorganic chemistry in
questions and answers" see on the TSU website http://tgumed.ru
tab “Student Help”, section “Lectures on
disciplines of the curriculum." And, of course, VK

Bioorganic chemistry studies the structure and properties of substances involved in life processes in connection with the knowledge of their biological

Bioorganic chemistry studies the structure and properties of substances
participating in life processes, in connection with
knowledge of their biological functions.
The main objects of study are biological
polymers (biopolymers) and bioregulators.
Biopolymers
–
high molecular weight
natural
compounds that are the structural basis of all living things
organisms and playing a certain role in the processes
life activity. Biopolymers include peptides and
proteins, polysaccharides (carbohydrates), nucleic acids. IN
This group also includes lipids, which themselves are not
are high molecular weight compounds, but in
the body are usually associated with other biopolymers.
Bioregulators are compounds that chemically
regulate metabolism. These include vitamins,
hormones, many synthetic biologically active
compounds, including drugs.

The set of chemical reactions occurring in the body is called metabolism, or metabolism. Substances formed in cells, such as

The set of chemical reactions occurring in the body
called metabolism, or metabolism. Substances
formed in cells, tissues and organs of plants and animals
during metabolism are called metabolites.
Metabolism includes two directions - catabolism and
anabolism.
Catabolism refers to the breakdown reactions of substances that enter
into the body with food. As a rule, they are accompanied by the oxidation of organic compounds and proceed with the release
energy.
Anabolism is the synthesis of complex molecules from
simpler ones, which results in the formation and renewal of the structural elements of a living organism.
Metabolic processes occur with the participation of enzymes,
those. specific proteins that are found in cells
organism and play the role of catalysts for biochemical
processes (biocatalysts).

Metabolism

catabolism
anabolism
Decomposition of biopolymers
with highlighting
energy
Synthesis of biopolymers
with absorption
energy
Glycerin and
fatty acid

Basic principles of the theory of the structure of organic compounds A.M. Butlerov

1. Atoms in a molecule are located in a certain
sequences according to their valency.
Valency of carbon atom in organic
connections is equal to four.
2. The properties of substances depend not only on what
atoms and in what quantities they are included in the composition
molecules, but also on the order in which they
connected to each other.
3. Atoms or groups of atoms that make up
molecules mutually influence each other, causing
depend on chemical activity and reaction
ability of molecules.
4. Studying the properties of substances allows us to determine them
chemical structure.

H o m o l o g h i c y r a y d

Homologous
row
A number of structurally similar compounds that have
similar chemical properties, in which individual
members of a series differ from each other only in quantity
groups -CH2- is called a homological series, and the group
CH2 – homological difference.
Members of any homologous series have an overwhelming
Most reactions proceed the same way (exception
constitute only the first members of the series). Therefore, knowing
chemical reactions of only one member of the series, it is possible with
with a high degree of probability to assert that the same
type of transformations also occur with the remaining members
homologous series.
For any homologous series one can derive
general formula reflecting the relationship between atoms
carbon and hydrogen in members of this series; this is the formula
is called the general formula of the homological series.

Classification of organic compounds according to the structure of the carbon skeleton

Classification of organic compounds according to the presence of functional groups

Functional group
Class
Example
halogen atoms (F, Cl, Br, I) halogen derivatives CH3CH2Cl (chloroethane)
hydroxyl (–OH)
alcohols (phenols)
CH3CH2OH (ethanol)
thiol or mercapto- (– thiols (mercaptans) CH3CH2SH (ethanethiol)
SН)
ethereal (–O–)
ethers
CH3CH2–O–CH2CH3
(diethyl
ether)
ester
carboxyl –C UN
esters
CH3CH2COOCH3 (methyl acetate)
carboxylic acids CH3COOH (acetic acid)
amide –С ОНН2
amides
carbonyl (–C=O)
sulfo- (–SO3H)
amino- (–NH2)
aldehydes and
ketones
sulfonic acids
amines
nitro- (–NO2)
nitro compounds
acids
CH3CONH2 (acetamide)
CH3CHO (ethanal)
CH3COCH3 (propanone)
СН3SO3Н (methanesulfonic acid)
CH3CH2NH2
(ethylamine,
primary amine)
CH3NHCH3
(dimethylamine,
secondary amine)
CH3CH2NO2 (nitroethane)

Nomenclature of organic compounds

Isomerism of organic compounds

If two or more individual substances have
identical quantitative composition (molecular formula),
but differ from each other in the binding sequence
atoms and (or) their location in space, then in general
In this case they are called isomers.
Since the structure of these compounds is different, then
chemical or physical properties of isomers
are different.
Types of isomerism: structural (structure isomers) and
stereoisomerism (spatial).
Structural isomerism can be of three types:
- isomerism of the carbon skeleton (chain isomers),
- position isomers (multiple bonds or functional
groups),
- isomers of the functional group (interclass).
Stereoisomerism is subdivided
configuration
on
conformational
And

This is geometric isomerism

Plane polarized light

Signs of optical activity:
- presence of an asymmetric carbon atom;
- absence of molecular symmetry elements

Enantiomers of adrenaline
protein
Anionic
Flat
center
surface
not occupied
Flat
Anionic
surface
center
busy
(+) - adrenaline
(-)- adrenaline
incomplete
correspondence
low
activity
complete
correspondence
high
activity

Biological activity of enantiomers

asparagine
DARVON
analgesic
NOVRAD
antitussive drug
mirror
L-asparagine
D-asparagine
(from asparagus)
(from peas)
bitter taste
sweet taste
enantiomers
Thalidomide victims

Acidity and basicity of organic compounds

Bronsted acids (protic acids) -
neutral molecules or ions that can
donate a proton (proton donors).
Typical Brønsted acids are carboxylic acids
acids. They have weaker acidic properties
hydroxyl groups of phenols and alcohols, as well as thio-,
amino and imino groups.
Bronsted bases are neutral molecules or
ions capable of accepting a proton (acceptors
protons).
Typical Bronsted bases are amines.
Ampholytes - compounds, in molecules
which contain both acidic and
main groups.

Types of acids and bases according to Brønsted

The main centers in the novocaine molecule

Use of basic properties to obtain water-soluble forms of drugs

Basic
properties
medicinal
drugs
are used to obtain their water-soluble forms.
When interacting with acids, compounds with
ionic bonds - salts that are highly soluble in water.
Yes, novocaine for injection
used in the form of hydrochloride.
the strongest main center,
which the proton joined

Acid-base properties of substances and their entry into the body

lipid
membrane
Stomach pH 1
UNS
lipid
membrane
blood plasma
pH 7.4
UNS
OSOSN3
Stomach pH 1
+
OSOSN3
NH3
SOOOOSCH3
SOO-
NH2
NH2
OSOSN3
Intestine pH 7-8
blood plasma
pH 7.4
Intestine pH 7-8
Acidic drugs are better absorbed from the stomach (pH 1-3),
and the absorption of drugs or xenobiotic bases occurs only
after they pass from the stomach to the intestines (pH 7-8). During
In one hour, almost 60% of acetylsalicylic acid is absorbed from the stomach of rats.
acid and only 6% aniline of the administered dose. In the intestines of rats
56% of the administered dose of aniline is already absorbed. Such a weak foundation
like caffeine (рKВH + 0.8), absorbed in the same time in a much greater
degree (36%), since even in the highly acidic environment of the stomach, caffeine
is predominantly in a non-ionized state.

Types of reactions in organic chemistry

Organic reactions are classified according to
following signs:
1. According to the electronic nature of the reagents.
2. By the change in the number of particles during the reaction.
3. Based on specific characteristics.
4. According to elementary mechanisms
stages of reactions.

Depending on the electronic nature of the reagents, reactions are distinguished: nucleophilic, electrophilic and free radical

Free radicals are electrically neutral particles
having an unpaired electron, for example: Cl, NO2.
Free radical reactions are characteristic of alkanes.
Electrophilic reagents are cations or molecules
which by themselves or in the presence of a catalyst
have an increased affinity for an electron pair or
negatively charged centers of molecules. These include
cations H+, Cl+, +NO2, +SO3H, R+ and molecules with free
orbitals AlCl3, ZnCl2, etc.
Electrophilic reactions are characteristic of alkenes, alkynes,
aromatic compounds (addition at a double bond,
proton substitution).
Nucleophilic reagents are anions or molecules
having centers with increased electron density. To them
include anions and molecules such as
HO-, RO-, Cl-, Br-, RCOO-, CN-, R-, NH3, C2H5OH, etc.

By change
number of particles during
reactions are distinguished
substitution reactions,
accessions,
splitting off
(elimination),
decomposition

Classification of reactions according to particular characteristics

Reactivity is always considered
only in relation to the reactionary partner.
During a chemical transformation, it is usually
not the whole molecule is affected, but only part of it -
reaction center.
An organic compound may contain
several unequal reaction centers.
Reactions can lead to isomeric products.
Reaction selectivity – qualitative
characteristic meaning predominant
reaction proceeds in one direction from
several possible ones.
There are regioselectivity,
chemoselectivity, stereoselectivity of the reaction.

Selectivity of reactions in organic chemistry

Regioselectivity - preferential reaction according to
one of several reaction centers of a molecule.
CH3-CH2-CH3 + Br2
СН3-СНВr-СН3 + НВr
The second isomer, 1-bromopropane, is practically not formed.
Chemoselectivity - preferential reaction according to
one of the related functional groups.
Stereoselectivity - preferential formation in a reaction
one of several possible stereoisomers.

Multifunctional compounds contain
several identical functional groups.
Heterofunctional compounds contain
several different functional groups.
Heteropolyfunctional
compounds contain both
different and the same
functional groups.

Properties of poly- and heterofunctional compounds

Each group in poly- and heterofunctional
compounds can undergo the same reactions as
corresponding group in monofunctional
connections

Specific properties of poly- and
heterofunctional compounds
Cyclization reactions
Formation of chelate complexes

Polyfunctional compounds as antidotes
The toxic effect of heavy metals is
binding of thiol groups of proteins. As a result, they are inhibited
vital enzymes of the body.
The principle of action of antidotes is the formation of strong
complexes with heavy metal ions.

Modern bioorganic chemistry is a branched field of knowledge, the foundation of many biomedical disciplines and, first of all, biochemistry, molecular biology, genomics, proteomics and

bioinformatics, immunology, pharmacology.

The program is based on a systematic approach to building the entire course on a single theoretical basis.

basis based on ideas about the electronic and spatial structure of organic

compounds and mechanisms of their chemical transformations. The material is presented in the form of 5 sections, the most important of which are: “Theoretical foundations of the structure of organic compounds and factors determining their reactivity”, “Biologically important classes of organic compounds” and “Biopolymers and their structural components. Lipids"

The program is aimed at specialized teaching of bioorganic chemistry at a medical university, and therefore the discipline is called “bioorganic chemistry in medicine.” The profiling of teaching bioorganic chemistry is served by consideration of the historical relationship between the development of medicine and chemistry, including organic, increased attention to classes of biologically important organic compounds (heterofunctional compounds, heterocycles, carbohydrates, amino acids and proteins, nucleic acids, lipids) as well as biologically important reactions of these classes of compounds ). A separate section of the program is devoted to consideration of the pharmacological properties of certain classes of organic compounds and the chemical nature of certain classes of drugs.

Considering the important role of “oxidative stress diseases” in the structure of modern human morbidity, the program pays special attention to free radical oxidation reactions, detection of end products of free radical lipid oxidation in laboratory diagnostics, natural antioxidants and antioxidant drugs. The program provides consideration of environmental problems, namely the nature of xenobiotics and the mechanisms of their toxic effect on living organisms.

1. The purpose and objectives of training.

1.1. The purpose of teaching the subject bioorganic chemistry in medicine is to develop an understanding of the role of bioorganic chemistry as the foundation of modern biology, a theoretical basis for explaining the biological effects of bioorganic compounds, the mechanisms of action of drugs and the creation of new drugs. To develop knowledge of the relationship between the structure, chemical properties and biological activity of the most important classes of bioorganic compounds, to teach how to apply the acquired knowledge when studying subsequent disciplines and in professional activities.

1.2. Objectives of teaching bioorganic chemistry:

1. Formation of knowledge of the structure, properties and reaction mechanisms of the most important classes of bioorganic compounds, which determine their medical and biological significance.

2. Formation of ideas about the electronic and spatial structure of organic compounds as a basis for explaining their chemical properties and biological activity.

3. Formation of skills and practical skills:

classify bioorganic compounds according to the structure of the carbon skeleton and functional groups;

use the rules of chemical nomenclature to indicate the names of metabolites, drugs, xenobiotics;

identify reaction centers in molecules;

be able to carry out qualitative reactions that have clinical and laboratory significance.

2. The place of discipline in the structure of OOP:

The discipline "Bioorganic chemistry" is an integral part of the discipline "Chemistry", which belongs to the mathematical, natural science cycle of disciplines.

The basic knowledge necessary to study the discipline is formed in the cycle of mathematical, natural science disciplines: physics, mathematics; medical informatics; chemistry; biology; anatomy, histology, embryology, cytology; normal physiology; microbiology, virology.

It is a prerequisite for studying the disciplines:

biochemistry;

pharmacology;

microbiology, virology;

immunology;

professional disciplines.

Disciplines studied in parallel, providing interdisciplinary connections within the framework of the basic part of the curriculum:

chemistry, physics, biology, 3. List of disciplines and topics that students need to master to study bioorganic chemistry.

General chemistry. The structure of the atom, the nature of a chemical bond, types of bonds, classes of chemical substances, types of reactions, catalysis, reaction of the medium in aqueous solutions.

Organic chemistry. Classes of organic substances, nomenclature of organic compounds, configuration of the carbon atom, polarization of atomic orbitals, sigma and pi bonds. Genetic relationship of classes of organic compounds. Reactivity of different classes of organic compounds.

Physics. The structure of the atom. Optics - ultraviolet, visible and infrared regions of the spectrum.

The interaction of light with matter - transmission, absorption, reflection, scattering. Polarized light.

Biology. Genetic code. Chemical basis of heredity and variability.

Latin language. Mastering terminology.

Foreign language. Ability to work with foreign literature.

4. Sections of the discipline and interdisciplinary connections with the provided (subsequent) disciplines No. sections of this discipline necessary for studying the provided No. Name of the provided sub-disciplines (subsequent) disciplines (subsequent) disciplines 1 2 3 4 5 1 Chemistry + + + + + Biology + - - + + Biochemistry + + + + + + 4 Microbiology, virology + + - + + + 5 Immunology + - - - + Pharmacology + + - + + + 7 Hygiene + - + + + Professional disciplines + - - + + + 5. Requirements for the level of mastery of the discipline content Achieving the learning goal The discipline “Bioorganic Chemistry” involves the implementation of a number of targeted problem tasks, as a result of which students must develop certain competencies, knowledge, skills, and must acquire certain practical skills.

5.1. The student must have:

5.1.1. General cultural competencies:

the ability and willingness to analyze socially significant problems and processes, to use in practice the methods of the humanities, natural sciences, biomedical and clinical sciences in various types of professional and social activities (OK-1);

5.1.2. Professional competencies (PC):

ability and willingness to apply basic methods, methods and means of obtaining, storing, processing scientific and professional information; receive information from various sources, including the use of modern computer tools, network technologies, databases and the ability and willingness to work with scientific literature, analyze information, conduct searches, turn what you read into a tool for solving professional problems (highlight the main provisions, consequences from them and suggestions);

ability and readiness to participate in setting scientific problems and their experimental implementation (PC-2, PC-3, PC-5, PC-7).

5.2. The student must know:

Principles of classification, nomenclature and isomerism of organic compounds.

Fundamentals of theoretical organic chemistry, which are the basis for studying the structure and reactivity of organic compounds.

The spatial and electronic structure of organic molecules and the chemical transformations of substances that are participants in life processes, in direct connection with their biological structure, chemical properties and biological role of the main classes of biologically important organic compounds.

5.3. The student must be able to:

Classify organic compounds according to the structure of the carbon skeleton and the nature of functional groups.

Compose formulas by name and name typical representatives of biologically important substances and drugs by structural formula.

Identify functional groups, acidic and basic centers, conjugated and aromatic fragments in molecules to determine the chemical behavior of organic compounds.

Predict the direction and result of chemical transformations of organic compounds.

5.4. The student must have:

Skills of independent work with educational, scientific and reference literature; conduct a search and draw general conclusions.

Have skills in handling chemical glassware.

Have the skills to work safely in a chemical laboratory and the ability to handle caustic, toxic, highly volatile organic compounds, work with burners, alcohol lamps and electric heating devices.

5.5. Forms of knowledge control 5.5.1. Current control:

Diagnostic control of material assimilation. It is carried out periodically mainly to control knowledge of formulaic material.

Educational computer control in every lesson.

Test tasks requiring the ability to analyze and generalize (see Appendix).

Scheduled colloquiums upon completion of the study of large sections of the program (see Appendix).

5.5.2 Final control:

Test (carried out in two stages):

C.2 - Mathematical, natural science and medical-biological General labor intensity:

2 Classification, nomenclature and Classification and classification characteristics of organic modern physical compounds: the structure of the carbon skeleton and the nature of the functional group.

chemical methods Functional groups, organic radicals. Biologically important studies of bioorganic classes of organic compounds: alcohols, phenols, thiols, ethers, sulfides, aldehyde compounds, ketones, carboxylic acids and their derivatives, sulfonic acids.

IUPAC nomenclature. Varieties of international nomenclature: substitutive and radical-functional nomenclature. The value of knowledge 3 Theoretical foundations of the structure of organic compounds and the Theory of the structure of organic compounds by A.M. Butlerov. The main factors determining their positions. Structural formulas. The nature of the carbon atom by position and reactivity. chains. Isomerism as a specific phenomenon of organic chemistry. Types of Stereoisomerism.

Chirality of molecules of organic compounds as a cause of optical isomerism. Stereoisomerism of molecules with one center of chirality (enantiomerism). Optical activity. Glyceraldehyde as a configuration standard. Fischer projection formulas. D and L System of Stereochemical Nomenclature. Ideas about R, S-nomenclature.

Stereoisomerism of molecules with two or more chirality centers: enantiomerism and diastereomerism.

Stereoisomerism in a series of compounds with a double bond (Pydiastereomerism). Cis and trans isomers. Stereoisomerism and biological activity of organic compounds.

Mutual influence of atoms: causes of occurrence, types and methods of its transmission in molecules of organic compounds.

Pairing. Pairing in open circuits (Pi-Pi). Conjugated bonds. Diene structures in biologically important compounds: 1,3-dienes (butadiene), polyenes, alpha, beta-unsaturated carbonyl compounds, carboxyl group. Coupling as a system stabilization factor. Conjugation energy. Conjugation in arenes (Pi-Pi) and heterocycles (p-Pi).

Aromaticity. Aromaticity criteria. Aromaticity of benzenoid (benzene, naphthalene, anthracene, phenanthrene) and heterocyclic (furan, thiophene, pyrrole, imidazole, pyridine, pyrimidine, purine) compounds. Widespread occurrence of conjugated structures in biologically important molecules (porphin, heme, etc.).

Bond polarization and electronic effects (inductive and mesomeric) as the cause of the uneven distribution of electron density in the molecule. Substituents are electron donors and electron acceptors.

The most important substituents and their electronic effects. Electronic effects of substituents and reactivity of molecules. Orientation rule in the benzene ring, substituents of the first and second kind.

Acidity and basicity of organic compounds.

Acidity and basicity of neutral molecules of organic compounds with hydrogen-containing functional groups (amines, alcohols, thiols, phenols, carboxylic acids). Acids and bases according to Bronsted-Lowry and Lewis. Conjugate pairs of acids and bases. Anion acidity and stability. Quantitative assessment of the acidity of organic compounds based on Ka and pKa values.

Acidity of various classes of organic compounds. Factors that determine the acidity of organic compounds: electronegativity of the nonmetal atom (C-H, N-H, and O-H acids); polarizability of a nonmetal atom (alcohols and thiols, thiol poisons); nature of the radical (alcohols, phenols, carboxylic acids).

Basicity of organic compounds. n-bases (heterocycles) and pi-bases (alkenes, alkanedienes, arenes). Factors that determine the basicity of organic compounds: electronegativity of the heteroatom (O- and N bases); polarizability of a nonmetal atom (O- and S-base); nature of the radical (aliphatic and aromatic amines).

The importance of the acid-base properties of neutral organic molecules for their reactivity and biological activity.

Hydrogen bonding as a specific manifestation of acid-base properties. General patterns of reactivity of organic compounds as the chemical basis of their biological functioning.

Reaction mechanisms of organic compounds.

Classification of reactions of organic compounds according to the result of substitution, addition, elimination, rearrangement, redox and according to the mechanism - radical, ionic (electrophilic, nucleophilic). Types of covalent bond cleavage in organic compounds and the resulting particles: homolytic cleavage (free radicals) and heterolytic cleavage (carbocations and carbonanions).

Electronic and spatial structure of these particles and factors determining their relative stability.

Homolytic radical substitution reactions in alkanes involving C-H bonds of the sp 3-hybridized carbon atom. Free radical oxidation reactions in a living cell. Reactive (radical) forms of oxygen. Antioxidants. Biological significance.

Electrophilic addition reactions (Ae): heterolytic reactions involving the Pi bond. Mechanism of ethylene halogenation and hydration reactions. Acid catalysis. Influence of static and dynamic factors on the regioselectivity of reactions. Peculiarities of reactions of addition of hydrogen-containing substances to the Pi bond in unsymmetrical alkenes. Markovnikov's rule. Features of electrophilic addition to conjugated systems.

Electrophilic substitution reactions (Se): heterolytic reactions involving an aromatic system. Mechanism of electrophilic substitution reactions in arenes. Sigma complexes. Reactions of alkylation, acylation, nitration, sulfonation, halogenation of arenes. Orientation rule.

Substitutes of the 1st and 2nd kind. Features of electrophilic substitution reactions in heterocycles. Orienting influence of heteroatoms.

Reactions of nucleophilic substitution (Sn) at sp3-hybridized carbon atom: heterolytic reactions caused by polarization of the carbon-heteroatom sigma bond (halogen derivatives, alcohols). The influence of electronic and spatial factors on the reactivity of compounds in nucleophilic substitution reactions.

Hydrolysis reaction of halogen derivatives. Alkylation reactions of alcohols, phenols, thiols, sulfides, ammonia and amines. The role of acid catalysis in nucleophilic substitution of the hydroxyl group.

Deamination of compounds with a primary amino group. Biological role of alkylation reactions.

Elimination reactions (dehydrohalogenation, dehydration).

Increased CH acidity as a cause of elimination reactions accompanying nucleophilic substitution at the sp3-hybridized carbon atom.

Nucleophilic addition reactions (An): heterolytic reactions involving the pi carbon-oxygen bond (aldehydes, ketones). Classes of carbonyl compounds. Representatives. Preparation of aldehydes, ketones, carboxylic acids. Structure and reactivity of the carbonyl group. Influence of electronic and spatial factors. Mechanism of An reactions: role of protonation in increasing carbonyl reactivity. Biologically important reactions of aldehydes and ketones: hydrogenation, oxidation-reduction of aldehydes (dismutation reaction), oxidation of aldehydes, formation of cyanohydrins, hydration, formation of hemiacetals, imines. Aldol addition reactions. Biological significance.

Nucleophilic substitution reactions at the sp2-hybridized carbon atom (carboxylic acids and their functional derivatives).

The mechanism of nucleophilic substitution reactions (Sn) at the sp2 hybridized carbon atom. Acylation reactions - the formation of anhydrides, esters, thioesters, amides - and their reverse hydrolysis reactions. Biological role of acylation reactions. Acidic properties of carboxylic acids according to the O-H group.

Oxidation and reduction reactions of organic compounds.

Redox reactions, electronic mechanism.

Oxidation states of carbon atoms in organic compounds. Oxidation of primary, secondary and tertiary carbon atoms. Oxidability of various classes of organic compounds. Ways of oxygen utilization in the cell.

Energetic oxidation. Oxidase reactions. Oxidation of organic substances is the main source of energy for chemotrophs. Plastic oxidation.

4 Biologically important classes of organic compounds Polyhydric alcohols: ethylene glycol, glycerol, inositol. Education Hydroxy acids: classification, nomenclature, representatives of lactic, betahydroxybutyric, gammahydroxybutyric, malic, tartaric, citric, reductive amination, transamination and decarboxylation.

Amino acids: classification, representatives of beta and gamma isomers: aminopropane, gamma-aminobutyric, epsilonaminocaproic. Reaction Salicylic acid and its derivatives (acetylsalicylic acid, antipyretic, anti-inflammatory and anti-rheumatic agent, enteroseptol and 5-NOK. The isoquinoline core as the basis of opium alkaloids, antispasmodics (papaverine) and analgesics (morphine). Acridine derivatives are disinfectants.

xanthine derivatives - caffeine, theobromine and theophylline, indole derivatives reserpine, strychnine, pilocarpine, quinoline derivatives - quinine, isoquinoline morphine and papaverine.

cephalosproins are derivatives of cephalosporanic acid, tetracyclines are derivatives of naphthacene, streptomycins are amyloglycosides. Semi-synthetic 5 Biopolymers and their structural components. Lipids. Definition. Classification. Functions.

Cyclo-oxotautomerism. Mutarotation. Derivatives of monosaccharides deoxysugar (deoxyribose) and amino sugar (glucosamine, galactosamine).

Oligosaccharides. Disaccharides: maltose, lactose, sucrose. Structure. Oglycosidic bond. Restorative properties. Hydrolysis. Biological (pathway of amino acid breakdown); radical reactions - hydroxylation (formation of oxy-derivatives of amino acids). Peptide bond formation.

Peptides. Definition. Structure of the peptide group. Functions.

Biologically active peptides: glutathione, oxytocin, vasopressin, glucagon, neuropeptides, kinin peptides, immunoactive peptides (thymosin), inflammatory peptides (difexin). The concept of cytokines. Antibiotic peptides (gramicidin, actinomycin D, cyclosporine A). Peptide toxins. Relationship between the biological effects of peptides and certain amino acid residues.

Squirrels. Definition. Functions. Levels of protein structure. The primary structure is the sequence of amino acids. Research methods. Partial and complete hydrolysis of proteins. The importance of determining the primary structure of proteins.

Directed site-specific mutagenesis as a method for studying the relationship between the functional activity of proteins and the primary structure. Congenital disorders of the primary structure of proteins - point mutations. Secondary structure and its types (alpha helix, beta structure). Tertiary structure.

Denaturation. The concept of active centers. Quaternary structure of oligomeric proteins. Cooperative properties. Simple and complex proteins: glycoproteins, lipoproteins, nucleoproteins, phosphoproteins, metalloproteins, chromoproteins.

Nitrogen bases, nucleosides, nucleotides and nucleic acids.

Definition of the concepts nitrogenous base, nucleoside, nucleotide and nucleic acid. Purine (adenine and guanine) and pyrimidine (uracil, thymine, cytosine) nitrogenous bases. Aromatic properties. Resistance to oxidative degradation as a basis for fulfilling a biological role.

Lactim - lactam tautomerism. Minor nitrogenous bases (hypoxanthine, 3-N-methyluracil, etc.). Derivatives of nitrogenous bases - antimetabolites (5-fluorouracil, 6-mercaptopurine).

Nucleosides. Definition. Formation of a glycosidic bond between a nitrogenous base and a pentose. Hydrolysis of nucleosides. Nucleosides antimetabolites (adenine arabinoside).

Nucleotides. Definition. Structure. Formation of a phosphoester bond during the esterification of the C5 hydroxyl of pentose with phosphoric acid. Hydrolysis of nucleotides. Macroerg nucleotides (nucleoside polyphosphates - ADP, ATP, etc.). Nucleotides-coenzymes (NAD+, FAD), structure, role of vitamins B5 and B2.

Nucleic acids - RNA and DNA. Definition. Nucleotide composition of RNA and DNA. Primary structure. Phosphodiester bond. Hydrolysis of nucleic acids. Definition of the concepts triplet (codon), gene (cistron), genetic code (genome). International Human Genome Project.

Secondary structure of DNA. The role of hydrogen bonds in the formation of secondary structure. Complementary pairs of nitrogenous bases. Tertiary structure of DNA. Changes in the structure of nucleic acids under the influence of chemicals. The concept of mutagenic substances.

Lipids. Definition, classification. Saponifiable and unsaponifiable lipids.

Natural higher fatty acids are components of lipids. The most important representatives: palmitic, stearic, oleic, linoleic, linolenic, arachidonic, eicosapentaenoic, docosohexaenoic (vitamin F).

Neutral lipids. Acylglycerols - natural fats, oils, waxes.

Artificial edible hydrofats. Biological role of acylglycerols.

Phospholipids. Phosphatidic acids. Phosphatidylcholines, phosphatidiethanolamines and phosphatidylserines. Structure. Participation in the formation of biological membranes. Lipid peroxidation in cell membranes.

Sphingolipids. Sphingosine and sphingomyelins. Glycolipids (cerebrosides, sulfatides and gangliosides).

Unsaponifiable lipids. Terpenes. Mono- and bicyclic terpenes 6 Pharmacological properties Pharmacological properties of some classes of mono-poly and some classes of heterofunctional compounds (hydrogen halides, alcohols, oxy- and organic compounds. oxoacids, benzene derivatives, heterocycles, alkaloids.). Chemical The chemical nature of some of the anti-inflammatory drugs, analgesics, antiseptics and classes of drugs. antibiotics.

6.3. Sections of disciplines and types of classes 1. Introduction to the subject. Classification, nomenclature and research of bioorganic compounds 2. Theoretical foundations of the structure of organic reactivity.

3. Biologically important classes of organic 5 Pharmacological properties of some classes of organic compounds. The chemical nature of some classes of drugs L-lectures; PZ – practical exercises; LR – laboratory work; C – seminars; SRS – independent work of students;

6.4 Thematic plan of lectures on discipline 1 1 Introduction to the subject. History of the development of bioorganic chemistry, significance for 3 2 Theory of the structure of organic compounds by A.M. Butlerov. Isomerism as 4 2 Mutual influence of atoms: causes of occurrence, types and methods of its transmission in 7 1.2 Test work in the sections “Classification, nomenclature and modern physicochemical methods for studying bioorganic compounds” and “Theoretical foundations of the structure of organic compounds and factors determining their reaction 15 5 Pharmacological properties of some classes of organic compounds. Chemical 19 4 14 Detection of insoluble calcium salts of higher carbonates 1 1 Introduction to the subject. Classification and Working with recommended literature.

nomenclature of bioorganic compounds. Completing a written assignment for 3 2 Mutual influence of atoms in molecules Work with recommended literature.

4 2 Acidity and basicity of organic materials Work with recommended literature.

5 2 Mechanisms of organic reactions Work with recommended literature.

6 2 Oxidation and reduction of organic materials Work with recommended literature.

7 1.2 Test work by section Work with recommended literature. * modern physical and chemical methods on the proposed topics, conducting research on bioorganic compounds”, information search in various organic compounds and factors, INTERNET and work with English-language databases 8 3 Heterofunctional bioorganic Work with recommended literature.

9 3 Biologically important heterocycles. Work with recommended literature.

10 3 Vitamins (laboratory work). Work with recommended literature.

12 4 Alpha amino acids, peptides and proteins. Work with recommended literature.

13 4 Nitrogen bases, nucleosides, Work with recommended literature.

nucleotides and nucleic acids. Completing a written writing task 15 5 Pharmacological properties of some Work with recommended literature.

classes of organic compounds. Completing a written assignment to write The chemical nature of some classes of chemical formulas of some medicinal * - tasks of the student's choice.

organic compounds.

organic molecules.

organic molecules.

organic compounds.

organic compounds.

connections. Stereoisomerism.

certain classes of drugs.

During the semester, a student can score a maximum of 65 points in practical classes.

In one practical lesson, a student can score a maximum of 4.3 points. This number consists of points scored for attending a class (0.6 points), completing an assignment for extracurricular independent work (1.0 points), laboratory work (0.4 points) and points awarded for an oral answer and a test task (from 1 .3 to 2.3 points). Points for attending classes, completing assignments for extracurricular independent work and laboratory work are awarded on a “yes” - “no” basis. Points for the oral answer and the test task are awarded differentiated from 1.3 to 2.3 points in the case of positive answers: 0-1.29 points correspond to the rating “unsatisfactory”, 1.3-1.59 - “satisfactory”, 1.6 -1.99 – “good”, 2.0-2.3 – “excellent”. On the test, a student can score a maximum of 5.0 points: attending class 0.6 points and giving an oral answer 2.0-4.4 points.

To be admitted to the test, a student must score at least 45 points, while the student’s current performance is assessed as follows: 65-75 points – “excellent”, 54-64 points – “good”, 45-53 points – “satisfactory”, less than 45 points – unsatisfactory. If a student scores from 65 to 75 points (“excellent” result), then he is exempt from the test and receives a “pass” mark in the grade book automatically, gaining 25 points for the test.

On the test, a student can score a maximum of 25 points: 0-15.9 points correspond to the grade “unsatisfactory”, 16-17.5 – “satisfactory”, 17.6-21.2 – “good”, 21.3-25 – “ Great".

Distribution of bonus points (up to 10 points per semester in total) 1. Lecture attendance – 0.4 points (100% lecture attendance – 6.4 points per semester);

2. Participation in UIRS up to 3 points, including:

writing an abstract on the proposed topic – 0.3 points;

preparation of a report and multimedia presentation for the final educational and theoretical conference 3. Participation in research work – up to 5 points, including:

attending a meeting of the student scientific circle at the department - 0.3 points;

preparing a report for a meeting of the student scientific circle – 0.5 points;

giving a report at a university student scientific conference – 1 point;

presentation at a regional, all-Russian and international student scientific conference – 3 points;

publication in collections of student scientific conferences – 2 points;

publication in a peer-reviewed scientific journal – 5 points;

4. Participation in educational work at the department up to 3 points, including:

participation in the organization of educational activities carried out by the department during extracurricular hours - 2 points for one event;

attending educational activities held by the department during extracurricular hours – 1 point for one event;

Distribution of penalty points (up to 10 points per semester in total) 1. Absence from lectures for an unexcused reason - 0.66-0.67 points (0% attendance at lectures - 10 points for If a student missed a lesson for a valid reason, he has the right to work out the lesson to improve your current rating.

If the absence is unexcused, the student must complete the class and receive a grade with a reduction factor of 0.8.

If a student is exempt from physical presence in classes (by order of the academy), then he is awarded maximum points if he completes the assignment for extracurricular independent work.

6. Educational, methodological and information support of the discipline 1. N.A. Tyukavkina, Yu.I. Baukov, S.E. Zurabyan. Bioorganic chemistry. M.:DROFA, 2009.

2. Tyukavkina N.A., Baukov Yu.I. Bioorganic chemistry. M.:DROFA, 2005.

1. Ovchinikov Yu.A. Bioorganic chemistry. M.: Education, 1987.

2. Riles A., Smith K., Ward R. Fundamentals of organic chemistry. M.: Mir, 1983.

3. Shcherbak I.G. Biological chemistry. Textbook for medical schools. S.-P. St. Petersburg State Medical University publishing house, 2005.

4. Berezov T.T., Korovkin B.F. Biological chemistry. M.: Medicine, 2004.

5. Berezov T.T., Korovkin B.F. Biological chemistry. M.: Medicine, Postupaev V.V., Ryabtseva E.G. Biochemical organization of cell membranes (textbook for students of pharmaceutical faculties of medical universities). Khabarovsk, Far Eastern State Medical University. 2001

7. Soros educational magazine, 1996-2001.

8. Guide to laboratory classes in bioorganic chemistry. Edited by N.A. Tyukavkina, M.:

Medicine, 7.3 Educational and methodological materials prepared by the department 1. Methodological development of practical classes in bioorganic chemistry for students.

2. Methodological developments for independent extracurricular work of students.

3. Borodin E.A., Borodina G.P. Biochemical diagnosis (physiological role and diagnostic value of biochemical parameters of blood and urine). Textbook 4th edition. Blagoveshchensk, 2010.

4. Borodina G.P., Borodin E.A. Biochemical diagnosis (physiological role and diagnostic value of biochemical parameters of blood and urine). Electronic textbook. Blagoveshchensk, 2007.

5. Assignments for computer testing of students’ knowledge in bioorganic chemistry (Compiled by Borodin E.A., Doroshenko G.K., Egorshina E.V.) Blagoveshchensk, 2003.

6. Test assignments in bioorganic chemistry for the exam in bioorganic chemistry for students of the medical faculty of medical universities. Toolkit. (Compiled by Borodin E.A., Doroshenko G.K.). Blagoveshchensk, 2002.

7. Test assignments in bioorganic chemistry for practical classes in bioorganic chemistry for students of the Faculty of Medicine. Toolkit. (Compiled by Borodin E.A., Doroshenko G.K.). Blagoveshchensk, 2002.

8. Vitamins. Toolkit. (Compiled by Egorshina E.V.). Blagoveshchensk, 2001.

8.5 Providing discipline with equipment and educational materials 1 Chemical glassware:

Glassware:

1.1 chemical test tubes 5000 Chemical experiments and analyzes in practical classes, UIRS, 1.2 centrifuge tubes 2000 Chemical experiments and analyzes in practical classes, UIRS, 1.3 glass rods 100 Chemical experiments and analyzes in practical classes, UIRS, 1.4. flasks of various volumes (for 200 Chemical experiments and analyzes in practical classes, UIRS, 1.5 large volume flasks - 0.5-2.0 30 Chemical experiments and analyzes in practical classes, UIRS, 1.6 chemical beakers of various 120 Chemical experiments and analyzes in practical classes, UIRS, 1.7 large chemical beakers 50 Chemical experiments and analyzes in practical classes, UIRS, preparation of workers 1.8 flasks of various sizes 2000 Chemical experiments and analyzes in practical classes, UIRS, 1.9 filter funnels 200 Chemical experiments and analyzes in practical classes, UIRS , 1.10 glassware Chemical experiments and analyzes in practical classes, CIRS, chromatography, etc.).

1.11 alcohol lamps 30 Chemical experiments and analyzes in practical classes, UIRS, Porcelain dishes 1.12 glasses different volumes (0.2- 30 Preparation of reagents for practical classes 1.13 mortars and pestles Preparation of reagents for practical classes, chemical experiments and 1.15 cups for evaporation 20 Chemical experiments and analyzes for practical classes, UIRS, Measuring glassware:

1.16 volumetric flasks of various 100 Preparation of reagents for practical classes, Chemical experiments 1.17 graduated cylinders of various 40 Preparation of reagents for practical classes, Chemical experiments 1.18 beakers of various volumes 30 Preparation of reagents for practical classes, Chemical experiments 1.19 measuring pipettes for 2000 Chemical experiments and analyzes for practical classes, UIRS, micropipettes) 1.20 mechanical automatic 15 Chemical experiments and analyzes in practical classes, UIRS, 1.21 mechanical automatic 2 Chemical experiments and analyzes in practical classes, UIRS, variable volume dispensers NIRS 1.22 electronic automatic 1 Chemical experiments and analyzes in practical classes, UIRS, 1.23 AC microsyringes 5 Chemical experiments and analyzes in practical classes, UIRS, 2 Technical equipment:

2.1 racks for test tubes 100 Chemical experiments and analyzes in practical classes, UIRS, 2.2 racks for pipettes 15 Chemical experiments and analyzes in practical classes, UIRS, 2.3 metal racks 15 Chemical experiments and analyzes in practical classes, UIRS, Heating devices:

2.4 drying cabinets 3 Drying chemical glassware, holding chemicals 2.5 air thermostats 2 Thermostating of the incubation mixture when determining 2.6 water thermostats 2 Thermostating of the incubation mixture when determining 2.7 electric stoves 3 Preparation of reagents for practical exercises, chemical experiments and 2.8 Refrigerators with freezers 5 Storage of chemical reagents, solutions and biological material for chambers “Chinar”, “Biryusa”, practical exercises , UIRS, NIRS "Stinol"

2.9 Storage cabinets 8 Storage of chemical reagents 2.10 Metal safe 1 Storage of toxic reagents and ethanol 3 General purpose equipment:

3.1 analytical damper 2 Gravimetric analysis in practical classes, UIRS, NIRS 3.6 Ultracentrifuge 1 Demonstration of the method of sedimentation analysis in practical classes (Germany) 3.8 Magnetic stirrers 2 Preparation of reagents for practical classes 3.9 Electric distiller DE - 1 Obtaining distilled water for preparing reagents for 3.10 Thermometers 10 Temperature control during chemical analyzes 3.11 Set of hydrometers 1 Measuring the density of solutions 4 Special-purpose equipment:

4.1 Apparatus for electrophoresis at 1 Demonstration of the method of electrophoresis of serum proteins at 4.2 Apparatus for electrophoresis at 1 Demonstration of the method for separating serum lipoproteins 4.3 Equipment for column Demonstration of the method for separating proteins using chromatography 4.4 Equipment for Demonstration of the TLC method for separating lipids at practical thin chromatography layer. classes, NIRS Measuring equipment:

Photoelectric colorimeters:

4.8 Photometer “SOLAR” 1 Measurement of light absorption of colored solutions at 4.9 Spectrophotometer SF 16 1 Measurement light absorption of solutions in the visible and UV regions 4.10 Clinical spectrophotometer 1 Measurement of light absorption of solutions in the visible and UV regions of the “Schimadzu - CL–770” spectrum using spectral methods of determination 4.11 Highly efficient 1 Demonstration of the HPLC method (practical exercises, UIRS, NIRS) liquid chromatograph "Milichrome - 4".

4.12 Polarimeter 1 Demonstration of the optical activity of enantiomers, 4.13 Refractometer 1 Demonstration refractometric method of determination 4.14 pH meters 3 Preparation of buffer solutions, demonstration of buffer 5 Projection equipment:

5.1 Multimedia projector and 2 Demonstration of multimedia presentations, photo and overhead projectors: Demonstration slides during lectures and practical classes 5.3 “Semi-automatic bearing” 5.6 Device for demonstration Assigned to the morphological educational building. Demonstration of transparent films (overhead) and illustrative material at lectures, during UIRS and NIRS film projector.

6 Computer technology:

6.1 Departmental network of 1 Access to educational resources of the INTERNET (national and personal computers with international electronic databases on chemistry, biology and access to INTERNET medicine) for teachers of the department and students in educational and 6.2 Personal computers 8 Creation by teachers of the department of printed and electronic staff of the department didactic materials during educational and methodological work, 6.3 Computer class for 10 1 Programmed testing of students’ knowledge in practical classes, during tests and exams (current, 7 Educational tables:

1. Peptide bond.

2. Regularity of the structure of the polypeptide chain.

3. Types of bonds in a protein molecule.

4. Disulfide bond.

5. Species specificity of proteins.

6. Secondary structure of proteins.

7. Tertiary structure of proteins.

8. Myoglobin and hemoglobin.

9. Hemoglobin and its derivatives.

10. Blood plasma lipoproteins.

11. Types of hyperlipidemia.

12. Electrophoresis of proteins on paper.

13. Scheme of protein biosynthesis.

14. Collagen and tropocollagen.

15. Myosin and actin.

16. Vitamin deficiency RR (pellagra).

17. Vitamin B1 deficiency.

18. Vitamin deficiency C.

19. Vitamin deficiency A.

20. Vitamin deficiency D (rickets).

21. Prostaglandins are physiologically active derivatives of unsaturated fatty acids.

22. Neuroxins formed from catechalamines and indolamines.

23. Products of non-enzymatic reactions of dopamine.

24. Neuropeptides.

25. Polyunsaturated fatty acids.

26. Interaction of liposomes with the cell membrane.

27. Free oxidation (differences from tissue respiration).

28. PUFAs of the omega 6 and omega 3 families.

2 Sets of slides for various sections of the program 8.6 Interactive learning tools (Internet technologies), multimedia materials, Electronic libraries and textbook, photo and video materials 1 Interactive learning tools (Internet technologies) 2 Multimedia materials Stonik V.A. (TIBOH DSC SB RAS) “Natural compounds are the basis 5 Borodin E.A. (AGMA) “The human genome. Genomics, proteomics and Author's presentation 6 Pivovarova E.N (Institute of Cytology and Genetics, Siberian Branch of the Russian Academy of Medical Sciences) “The role of regulation of gene expression Author’s presentation of a person.”

3 Electronic libraries and textbooks:

2 MEDLINE. CD version of electronic databases on chemistry, biology and medicine.

3 Life Sciences. CD version of electronic databases on chemistry and biology.

4 Cambridge Scientific Abstracts. CD version of electronic databases on chemistry and biology.

5 PubMed - electronic database of the National Institute of Health http://www.ncbi.nlm.nih.gov/pubmed/ Organic chemistry. Digital library. (Compiled by N.F. Tyukavkina, A.I. Khvostova) - M., 2005.

Organic and general chemistry. Medicine. Lectures for students, course. (Electronic manual). M., 2005

4 Videos:

3 MES TIBOKH DSC FEB RAS CD

5 Photo and video materials:

Author's photos and video materials of the head. department prof. E.A. Borodin about 1 universities of Uppsala (Sweden), Granada (Spain), medical schools of universities in Japan (Niigata, Osaka, Kanazawa, Hirosaki), Institute of Biomedical Chemistry of the Russian Academy of Medical Sciences, Institute of Physical Chemistry and Chemistry of the Ministry of Health of Russia, TIBOKHE DSC. FEB RAS.

8.1. Examples of current control test items (with standard answers) for lesson No. 4 “Acidity and basicity organic molecules"

1. Select the characteristic features of Bronsted-Lowry acids:

1. increase the concentration of hydrogen ions in aqueous solutions 2. increase the concentration of hydroxide ions in aqueous solutions 3. are neutral molecules and ions - proton donors 4. are neutral molecules and ions - proton acceptors 5. do not affect the reaction of the medium 2. Specify the factors , affecting the acidity of organic molecules:

1. electronegativity of the heteroatom 2. polarizability of the heteroatom 3. nature of the radical 4. ability to dissociate 5. solubility in water 3. Select the strongest Bronsted acids from the listed compounds:

1. alkanes 2. amines 3. alcohols 4. thiols 5. carboxylic acids 4. Indicate the characteristic features of organic compounds that have the properties of bases:

1. proton acceptors 2. proton donors 3. upon dissociation give hydroxyl ions 4. do not dissociate 5. basic properties determine reactivity 5. Select the weakest base from the given compounds:

1. ammonia 2. methylamine 3. phenylamine 4. ethylamine 5. propylamine 8.2 Examples of situational tasks of current control (with answer standards) 1. Determine the parent structure in the compound:

Solution. The choice of parent structure in the structural formula of an organic compound is regulated in the IUPAC substitutive nomenclature by a number of consistently applied rules (see Textbook, 1.2.1).

Each subsequent rule is applied only when the previous one does not allow making a clear choice. Compound I contains aliphatic and alicyclic fragments. According to the first rule, the structure with which the senior characteristic group is directly related is chosen as the parent structure. Of the two characteristic groups present in compound I (OH and NH), the hydroxyl group is the oldest. Therefore, the initial structure will be cyclohexane, which is reflected in the name of this compound - 4-aminomethylcyclohexanol.

2. The basis of a number of biologically important compounds and drugs is a condensed heterocyclic purine system, including pyrimidine and imidazole nuclei. What explains the increased resistance of purine to oxidation?

Solution. Aromatic compounds have high conjugation energy and thermodynamic stability. One of the manifestations of aromatic properties is resistance to oxidation, although “externally”

aromatic compounds have a high degree of unsaturation, which usually makes them prone to oxidation. To answer the question posed in the problem statement, it is necessary to establish whether purine belongs to aromatic systems.

According to the definition of aromaticity, a necessary (but not sufficient) condition for the emergence of a conjugated closed system is the presence in the molecule of a flat cyclic skeleton with a single electron cloud. In the purine molecule, all carbon and nitrogen atoms are in a state of sp2 hybridization, and therefore all the bonds lie in the same plane. Due to this, the orbitals of all atoms included in the cycle are located perpendicular to the skeletal plane and parallel to each other, which creates conditions for their mutual overlap with the formation of a single closed delocalized ti-electron system covering all the atoms of the cycle (circular conjugation).

Aromaticity is also determined by the number of -electrons, which must correspond to the formula 4/7 + 2, where n is a series of natural numbers O, 1, 2, 3, etc. (Hückel's rule). Each carbon atom and the pyridine nitrogen atoms in positions 1, 3 and 7 contribute one p-electron to the conjugated system, and the pyrrole nitrogen atom in position 9 contributes a lone pair of electrons. The conjugated purine system contains 10 electrons, which corresponds to Hückel's rule at n = 2.

Thus, the purine molecule has an aromatic character and its resistance to oxidation is associated with this.

The presence of heteroatoms in the purine cycle leads to uneven distribution of electron density. Pyridine nitrogen atoms exhibit an electron-withdrawing character and reduce the electron density on carbon atoms. In this regard, the oxidation of purine, generally considered as the loss of electrons by the oxidizing compound, will be even more difficult compared to benzene.

8.3 Test tasks for testing (one option in full with answer standards) 1.Name the organogenic elements:

7.Si 8.Fe 9.Cu 2.Indicate functional groups that have a Pi bond:

1.Carboxyl 2.amino group 3.hydroxyl 4.oxo group 5.carbonyl 3.Indicate the senior functional group:

1.-C=O 2.-SO3H 3.-CII 4.-COOH 5.-OH 4.Which class of organic compounds does lactic acid CH3-CHOH-COOH, formed in tissues as a result of the anaerobic breakdown of glucose, belong to?

1.Carboxylic acids 2.Hydroxy acids 3.Amino acids 4.Keto acids 5.Name by substitution nomenclature the substance that is the main energy fuel of the cell and has the following structure:

CH2-CH -CH -CH -CH -C=O

I I III I

OH OH OH OH OH H

1. 2,3,4,5,6-pentahydroxyhexanal 2.6-oxohexanepnentanol 1,2,3,4, 3. Glucose 4. Hexose 5.1,2,3,4,5-pentahydroxyhexanal- 6. Indicate the characteristic features of conjugated systems:

1. Equalization of the electron density of sigma and pi bonds 2. Stability and low reactivity 3. Instability and high reactivity 4. Contain alternating sigma and pi bonds 5. Pi bonds are separated by -CH2 groups 7. For which compounds characteristic Pi-Pi conjugation:

1. carotenes and vitamin A 2. pyrrole 3. pyridine 4. porphyrins 5. benzpyrene 8. Select substituents of the first kind, orienting to the ortho- and para-positions:

1.alkyl 2.- OH 3.- NH 4.- COOH 5.- SO3H 9. What effect does the -OH group have in aliphatic alcohols:

1. Positive inductive 2. Negative inductive 3. Positive mesomeric 4. Negative mesomeric 5. The type and sign of the effect depend on the position of the -OH group 10. Select the radicals that have a negative mesomeric effect 1. Halogens 2. Alkyl radicals 3. Amino group 4. Hydroxy group 5. Carboxy group 11. Select the characteristic features of Bronsted-Lowry acids:

1. increase the concentration of hydrogen ions in aqueous solutions 2. increase the concentration of hydroxide ions in aqueous solutions 3. are neutral molecules and ions - proton donors 4. are neutral molecules and ions - proton acceptors 5. do not affect the reaction of the medium 12. Specify the factors , affecting the acidity of organic molecules:

1. electronegativity of the heteroatom 2. polarizability of the heteroatom 3. nature of the radical 4. ability to dissociate 5. solubility in water 13. Select the strongest Bronsted acids from the listed compounds:

1. alkanes 2. amines 3. alcohols 4. thiols 5. carboxylic acids 14. Indicate the characteristic features of organic compounds that have the properties of bases:

1. proton acceptors 2. proton donors 3. upon dissociation they give hydroxyl ions 4. do not dissociate 5. basic properties determine reactivity 15. Select the weakest base from the given compounds:

1. ammonia 2. methylamine 3. phenylamine 4. ethylamine 5. propylamine 16. What features are used to classify reactions of organic compounds:

1. The mechanism of breaking a chemical bond 2. The final result of the reaction 3. The number of molecules participating in the stage that determines the rate of the entire process 4. The nature of the reagent attacking the bond 17. Select the active forms of oxygen:

1. singlet oxygen 2. peroxide diradical -O-O-Superoxide ion 4. hydroxyl radical 5. triplet molecular oxygen 18. Select the characteristic features of electrophilic reagents:

1.particles that carry a partial or complete positive charge 2.are formed by the homolytic cleavage of a covalent bond 3.particles that carry an unpaired electron 4.particles that carry a partial or complete negative charge 5.are formed by the heterolytic cleavage of a covalent bond 19.Select compounds for which Characteristic reactions are electrophilic substitution:

1. alkenes 2. arenes 3. alkadienes 4. aromatic heterocycles 5. alkanes 20. Indicate the biological role of free radical oxidation reactions:

1. phagocytic activity of cells 2. universal mechanism of destruction of cell membranes 3. self-renewal of cellular structures 4. play a decisive role in the development of many pathological processes 21. Select which classes of organic compounds are characterized by nucleophilic substitution reactions:

1. alcohols 2. amines 3. halogen derivatives of hydrocarbons 4. thiols 5. aldehydes 22. In what order does the reactivity of substrates decrease in nucleophilic substitution reactions:

1. halogen derivatives of hydrocarbons, amine alcohols 2. amine alcohols, halogen derivatives of hydrocarbons 3. amine alcohols, halogen derivatives of hydrocarbons 4. halogen derivatives of hydrocarbons, amine alcohols 23. Select polyhydric alcohols from the listed compounds:

1. ethanol 2. ethylene glycol 3. glycerol 4. xylitol 5. sorbitol 24. Choose what is characteristic of this reaction:

CH3-CH2OH --- CH2=CH2 + H2O 1. elimination reaction 2. intramolecular dehydration reaction 3. occurs in the presence of mineral acids when heated 4. occurs under normal conditions 5. intermolecular dehydration reaction 25. What properties appear when an organic substance is introduced into a molecule chlorine substances:

1. narcotic properties 2. lachrymatory (tearing) 3. antiseptic properties 26. Select the reactions characteristic of the SP2-hybridized carbon atom in oxo compounds:

1. nucleophilic addition 2. nucleophilic substitution 3. electrophilic addition 4. homolytic reactions 5. heterolytic reactions 27. In what order does the ease of nucleophilic attack of carbonyl compounds decrease:

1. aldehydes ketones anhydrides esters amides salts of carboxylic acids 2. ketones aldehydes anhydrides esters amides salts of carboxylic acids 3. anhydrides aldehydes ketones esters amides salts of carboxylic acids 28. Determine what is characteristic of this reaction:

1.qualitative reaction to aldehydes 2.aldehyde is a reducing agent, silver oxide (I) is an oxidizing agent 3.aldehyde is an oxidizing agent, silver oxide (I) is a reducing agent 4.redox reaction 5.occurs in an alkaline medium 6.characteristic of ketones 29 .Which of the following carbonyl compounds undergo decarboxylation to form biogenic amines?

1. carboxylic acids 2. amino acids 3. oxo acids 4. hydroxy acids 5. benzoic acid 30. How do acid properties change in the homologous series of carboxylic acids:

1. increase 2. decrease 3. do not change 31. Which of the proposed classes of compounds are heterofunctional:

1. hydroxy acids 2. oxo acids 3. amino alcohols 4. amino acids 5. dicarboxylic acids 32. Hydroxy acids include:

1. citric 2. butyric 3. acetoacetic 4. pyruvic 5. malic 33. Select medications - derivatives of salicylic acid:

1. paracetamol 2. phenacetin 3. sulfonamides 4. aspirin 5. PAS 34. Select drugs - p-aminophenol derivatives:

1. paracetamol 2. phenacetin 3. sulfonamides 4. aspirin 5. PAS 35. Select drugs - sulfanilic acid derivatives:

1. paracetamol 2. phenacetin 3. sulfonamides 4. aspirin 5. PASK 36. Select the main provisions of the theory of A.M. Butlerov:

1. carbon atoms are connected by simple and multiple bonds 2. carbon in organic compounds is tetravalent 3. the functional group determines the properties of the substance 4. carbon atoms form open and closed cycles 5. in organic compounds carbon is in a reduced form 37. Which isomers are classified as spatial:

1. chains 2. position of multiple bonds 3. functional groups 4. structural 5. configurational 38. Choose what is characteristic of the concept “conformation”:

1. the possibility of rotation around one or more sigma bonds 2. conformers are isomers 3. a change in the sequence of bonds 4. a change in the spatial arrangement of substituents 5. a change in the electronic structure 39. Choose the similarity between enantiomers and diastereomers:

1. have the same physicochemical properties 2. are able to rotate the plane of polarization of light 3. are not able to rotate the plane of polarization of light 4. are stereoisomers 5. are characterized by the presence of a center of chirality 40. Select the similarity between configurational and conformational isomerism:

1. Isomerism is associated with different positions in space of atoms and groups of atoms 2. Isomerism is due to the rotation of atoms or groups of atoms around a sigma bond 3. Isomerism is due to the presence of a center of chirality in the molecule 4. Isomerism is due to different arrangements of substituents relative to the pi bond plane.

41.Name the heteroatoms that make up biologically important heterocycles:

1.nitrogen 2.phosphorus 3.sulfur 4.carbon 5.oxygen 42.Indicate the 5-membered heterocycle that is part of porphyrins:

1.pyrrolidine 2.imidazole 3.pyrrole 4.pyrazole 5.furan 43.Which heterocycle with one heteroatom is part of nicotinic acid:

1. purine 2. pyrazole 3. pyrrole 4. pyridine 5. pyrimidine 44. Name the final product of purine oxidation in the body:

1. hypoxanthine 2. xanthine 3. uric acid 45. Specify opium alkaloids:

1. strychnine 2. papaverine 4. morphine 5. reserpine 6. quinine 6. What oxidation reactions are characteristic of the human body:

1.dehydrogenation 2.addition of oxygen 3.donation of electrons 4.addition of halogens 5.interaction with potassium permanganate, nitric and perchloric acids 47.What determines the degree of oxidation of a carbon atom in organic compounds:

1. the number of its bonds with atoms of elements more electronegative than hydrogen 2. the number of its bonds with oxygen atoms 3. the number of its bonds with hydrogen atoms 48. What compounds are formed during the oxidation of the primary carbon atom?

1. primary alcohol 2. secondary alcohol 3. aldehyde 4. ketone 5. carboxylic acid 49. Determine what is characteristic of oxidase reactions:

1. oxygen is reduced to water 2. oxygen is included in the composition of the oxidized molecule 3. oxygen goes to the oxidation of hydrogen split off from the substrate 4. reactions have an energetic value 5. reactions have a plastic value 50. Which of the proposed substrates is oxidized more easily in the cell and why?

1. glucose 2. fatty acid 3. contains partially oxidized carbon atoms 4. contains fully hydrogenated carbon atoms 51. Select aldoses:

1. glucose 2. ribose 3. fructose 4. galactose 5. deoxyribose 52. Select the reserve forms of carbohydrates in a living organism:

1. fiber 2. starch 3. glycogen 4. hyaluric acid 5. sucrose 53. Select the most common monosaccharides in nature:

1. trioses 2. tetroses 3. pentoses 4. hexoses 5. heptoses 54. Select amino sugars:

1. beta-ribose 2. glucosamine 3. galactosamine 4. acetylgalactosamine 5. deoxyribose 55. Select the products of monosaccharide oxidation:

1. glucose-6-phosphate 2. glyconic (aldonic) acids 3. glycuronic (uronic) acids 4. glycosides 5. esters 56. Select disaccharides:

1. maltose 2. fiber 3. glycogen 4. sucrose 5. lactose 57. Select homopolysaccharides:

1. starch 2. cellulose 3. glycogen 4. dextran 5. lactose 58. Select which monosaccharides are formed during the hydrolysis of lactose:

1.beta-D-galactose 2.alpha-D-glucose 3.alpha-D-fructose 4.alpha-D-galactose 5.alpha-D-deoxyribose 59. Choose what is characteristic of cellulose:

1. linear, plant polysaccharide 2. structural unit is beta-D-glucose 3. necessary for normal nutrition, is a ballast substance 4. the main carbohydrate in humans 5. does not break down in the gastrointestinal tract 60. Select the carbohydrate derivatives that make up muramin:

1.N-acetylglucosamine 2.N-acetylmuramic acid 3.glucosamine 4.glucuronic acid 5.ribulose-5-phosphate 61.Choose the correct statements from the following: Amino acids are...

1. compounds containing both amino and hydroxy groups in the molecule 2. compounds containing hydroxyl and carboxyl groups 3. are derivatives of carboxylic acids in the radical of which hydrogen is replaced by an amino group 4. compounds containing oxo and carboxyl groups in the molecule 5. compounds containing hydroxy and aldehyde groups 62. How are amino acids classified?

1. by the chemical nature of the radical 2. by physicochemical properties 3. by the number of functional groups 4. by the degree of unsaturation 5. by the nature of additional functional groups 63. Select an aromatic amino acid:

1. glycine 2. serine 3. glutamic 4. phenylalanine 5. methionine 64. Select an amino acid that exhibits acidic properties:

1. leucine 2. tryptophan 3. glycine 4. glutamic acid 5. alanine 65. Select a basic amino acid:

1. serine 2. lysine 3. alanine 4. glutamine 5. tryptophan 66. Select purine nitrogenous bases:

1. thymine 2. adenine 3. guanine 4. uracil 5. cytosine 67. Select pyrimidine nitrogenous bases:

1.uracil 2.thymine 3.cytosine 4.adenine 5.guanine 68.Select the components of the nucleoside:

1.purine nitrogenous bases 2.pyrimidine nitrogenous bases 3.ribose 4.deoxyribose 5.phosphoric acid 69.Indicate the structural components of nucleotides:

1. purine nitrogenous bases 2. pyrimidine nitrogenous bases 3. ribose 4. deoxyribose 5. phosphoric acid 70. Indicate the distinctive features of DNA:

1. formed by one polynucleotide chain 2. formed by two polynucleotide chains 3. contains ribose 4. contains deoxyribose 5. contains uracil 6. contains thymine 71. Select saponifiable lipids:

1. neutral fats 2. triacylglycerols 3. phospholipids 4. sphingomyelins 5. steroids 72. Select unsaturated fatty acids:

1. palmitic 2. stearic 3. oleic 4. linoleic 5. arachidonic 73. Specify the characteristic composition of neutral fats:

1.mericyl alcohol + palmitic acid 2.glycerol + butyric acid 3.sphingosine + phosphoric acid 4.glycerol + higher carboxylic acid + phosphoric acid 5.glycerol + higher carboxylic acids 74. Choose what function phospholipids perform in the human body:

1. regulatory 2. protective 3. structural 4. energetic 75. Select glycolipids:

1.phosphatidylcholine 2.cerebrosides 3.sphingomyelins 4.sulfatides 5.gangliosides

ANSWERS TO TEST TASKS

8.4 List of practical skills and tasks (in full) required for passing 1. The ability to classify organic compounds according to the structure of the carbon skeleton and 2. The ability to draw up formulas by name and name typical representatives of biologically important substances and drugs by structural formula.

3. The ability to isolate functional groups, acidic and basic centers, conjugated and aromatic fragments in molecules to determine chemical behavior 4. The ability to predict the direction and result of organic chemical transformations 5. Possession of the skills of independent work with educational, scientific and reference literature; conduct a search and draw general conclusions.

6. Possession of skills in handling chemical glassware.

7. Possession of safe work skills in a chemical laboratory and the ability to handle caustic, poisonous, highly volatile organic compounds, work with burners, alcohol lamps and electric heating devices.

1. Subject and tasks of bioorganic chemistry. Implications in medical education.

2. The elemental composition of organic compounds, as the reason for their compliance with biological processes.

3. Classification of organic compounds. Classes, general formulas, functional groups, individual representatives.

4. Nomenclature of organic compounds. Trivial names. Substitute IUPAC nomenclature.

5. Main functional groups. Parental structure. Deputies. Seniority of groups, deputies. Names of functional groups and substituents as prefixes and endings.

6. Theoretical foundations of the structure of organic compounds. Theory of A.M. Butlerov.

Structural formulas. Structural isomerism. Chain and position isomers.

7. Spatial structure of organic compounds. Stereochemical formulas.

Molecular models. The most important concepts in stereochemistry are the configuration and conformation of organic molecules.

8. Conformations of open chains - eclipsed, inhibited, oblique. Energy and reactivity of different conformations.

9. Conformations of cycles using the example of cyclohexane (chair and bath). Axial and equatorial connections.

10. Mutual influence of atoms in molecules of organic compounds. Its causes, types of manifestation. Influence on the reactivity of molecules.

11.Pairing. Conjugate systems, conjugate connections. Pi-pi conjugation in dienes. Conjugation energy. Stability of coupled systems (vitamin A).

12. Pairing in arenas (pi-pi pairing). Aromaticity. Hückel's rule. Benzene, naphthalene, phenanthrene. Reactivity of the benzene ring.

13. Conjugation in heterocycles (p-pi and pi-pi conjugation using the example of pyrrole and pyridine).

Stability of heterocycles - biological significance using the example of tetrapyrrole compounds.

14.Polarization of bonds. Causes. Polarization in alcohols, phenols, carbonyl compounds, thiols. Influence on the reactivity of molecules.\ 15.Electronic effects. Inductive effect in molecules containing sigma bonds. Sign of the inductive effect.

16.Mesomeric effect in open chains with conjugated pi bonds using the example of 1,3 butadiene.

17.Mesomeric effect in aromatic compounds.

18.Electron-donating and electron-withdrawing substituents.

19. Deputies of the 1st and 2nd kind. Rule of orientation in the benzene ring.

20.Acidity and basicity of organic compounds. Brendstet-Lowry acids and bases.

Acid-base pairs are conjugate acids and bases. Ka and pKa are quantitative characteristics of the acidity of organic compounds. The importance of acidity for the functional activity of organic molecules.

21.Acidity of various classes of organic compounds. Factors that determine the acidity of organic compounds are the electronegativity of the non-metal atom bonded to hydrogen, the polarizability of the non-metal atom, the nature of the radical bonded to the non-metal atom.

22.Organic bases. Amines. Reason for basicity. The influence of radicals on the basicity of aliphatic and aromatic amines.

23. Classification of reactions of organic compounds according to their mechanism. Concepts of homolytic and heterolytic reactions.

24. Radical substitution reactions in alkanes. Free radical oxidation in living organisms. Reactive oxygen species.

25. Electrophilic addition in alkenes. Formation of Pi-complexes, carbocations. Reactions of hydration, hydrogenation.

26. Electrophilic substitution in the aromatic ring. Formation of intermediate sigmacomplexes. Benzene bromination reaction.

27.Nucleophilic substitution in alcohols. Reactions of dehydration, oxidation of primary and secondary alcohols, formation of esters.

28.Nucleophilic addition of carbonyl compounds. Biologically important reactions of aldehydes: oxidation, formation of hemiacetals when interacting with alcohols.

29.Nucleophilic substitution in carboxylic acids. Biologically important reactions of carboxylic acids.

30. Oxidation of organic compounds, biological significance. The degree of oxidation of carbon in organic molecules. Oxidability of different classes of organic compounds.

31.Energetic oxidation. Oxidase reactions.

32.Non-energetic oxidation. Oxygenase reactions.

33. The role of free radical oxidation in the bactericidal action of phagocytic cells.

34. Restoration of organic compounds. Biological significance.

35.Multifunctional compounds. Polyhydric alcohols - ethylene glycol, glycerin, xylitol, sorbitol, inositol. Biological significance. Biologically important reactions of glycerol are oxidation and formation of esters.

36.Dibasic dicarboxylic acids: oxalic, malonic, succinic, glutaric.

The conversion of succinic acid to fumaric acid is an example of biological dehydrogenation.

37. Amines. Classification:

By the nature of the radical (aliphatic and aromatic); -by the number of radicals (primary, secondary, tertiary, quaternary ammonium bases); -by the number of amino groups (mono- and diamines-). Diamines: putrescine and cadaverine.

38. Heterofunctional compounds. Definition. Examples. Features of the manifestation of chemical properties.

39. Amino alcohols: ethanolamine, choline, acetylcholine. Biological significance.

40.Hydroxyacids. Definition. General formula. Classification. Nomenclature. Isomerism.

Representatives of monocarboxylic hydroxy acids: lactic, beta-hydroxybutyric, gamma-xibutyric;

dicarbonate: apple, wine; tricarboxylic: lemon; aromatic: salicylic.

41. Chemical properties of hydroxy acids: by carboxyl, by hydroxyl group, dehydration reactions of alpha, beta and gamma isomers, difference in reaction products (lactides, unsaturated acids, lactones).

42.Stereoisomerism. Enantiomers and diastereomers. Chirality of molecules of organic compounds as a cause of optical isomerism.

43. Enantiomers with one chirality center (lactic acid). Absolute and relative configuration of enantiomers. Oxyacid key. D and L glyceraldehyde. D and L isomers.

Racemates.

44. Enantiomers with several centers of chirality. Tartaric and mesotartaric acids.

45.Stereoisomerism and biological activity of stereoisomers.

46.Cis-and trans-isomerism using the example of fumaric and maleic acids.

47.Oxoacids. Definition. Biologically important representatives: pyruvic acid, acetoacetic acid, oxaloacetic acid. Ketoenol tautomerism using the example of pyruvic acid.

48. Amino acids. Definition. General formula. Isomers of amino group position (alpha, beta, gamma). Biological significance of alpha amino acids. Representatives of beta-, gamma- and other isomers (beta-aminopropionic, gamma-aminobutyric, epsilonaminocaproic). Dehydration reaction of gamma isomers with the formation of cyclic lactones.

49. Heterofunctional benzene derivatives as the basis of medicines. Derivatives of p-aminobenzoic acid - PABA (folic acid, anesthesin). PABA antagonists are sulfanilic acid derivatives (sulfonamides - streptocide).

50. Heterofunctional benzene derivatives - medicines. Raminophenol derivatives (paracetamol), salicylic acid derivatives (acetylsalicylic acid). Raminosalicylic acid - PAS.

51.Biologically important heterocycles. Definition. Classification. Features of structure and properties: conjugation, aromaticity, stability, reactivity. Biological significance.

52. Five-membered heterocycles with one heteroatom and their derivatives. Pyrrole (porphin, porphyrins, heme), furan (medicines), thiophene (biotin).

53. Five-membered heterocycles with two heteroatoms and their derivatives. Pyrazole (5-oxo derivatives), imidazole (histidine), thiazole (vitamin B1-thiamine).

54. Six-membered heterocycles with one heteroatom and their derivatives. Pyridine (nicotinic acid - participation in redox reactions, vitamin B6-pyridoxal), quinoline (5-NOK), isoquinoline (alkaloids).

55. Six-membered heterocycles with two heteroatoms. Pyrimidine (cytosine, uracil, thymine).

56.Fused heterocycles. Purine (adenine, guanine). Purine oxidation products hypoxanthine, xanthine, uric acid).

57. Alkaloids. Definition and general characteristics. The structure of nicotine and caffeine.

58.Carbohydrates. Definition. Classification. Functions of carbohydrates in living organisms.

59.Monosugars. Definition. Classification. Representatives.

60.Pentoses. Representatives are ribose and deoxyribose. Structure, open and cyclic formulas. Biological significance.

61.Hexoses. Aldoses and ketoses. Representatives.

62.Open formulas of monosaccharides. Determination of stereochemical configuration. Biological significance of the configuration of monosaccharides.

63. Formation of cyclic forms of monosaccharides. Glycosidic hydroxyl. Alpha and beta anomers. Haworth's formulas.

64. Derivatives of monosaccharides. Phosphorus esters, glyconic and glycuronic acids, amino sugars and their acetyl derivatives.

65. Maltose. Composition, structure, hydrolysis and significance.

66.Lactose. Synonym. Composition, structure, hydrolysis and significance.

67.Sucrose. Synonyms. Composition, structure, hydrolysis and significance.

68. Homopolysaccharides. Representatives. Starch, structure, properties, hydrolysis products, significance.

69.Glycogen. Structure, role in the animal body.

70. Fiber. Structure, role in plants, significance for humans.

72. Heteropolysaccharides. Synonyms. Functions. Representatives. Structural features: dimer units, composition. 1,3- and 1,4-glycosidic bonds.

73.Hyaluronic acid. Composition, structure, properties, significance in the body.

74.Chondroitin sulfate. Composition, structure, significance in the body.

75.Muramin. Composition, meaning.

76. Alpha amino acids. Definition. General formula. Nomenclature. Classification. Individual representatives. Stereoisomerism.

77. Chemical properties of alpha amino acids. Amphotericity, reactions of decarboxylation, deamination, hydroxylation in the radical, formation of a peptide bond.

78.Peptides. Individual peptides. Biological role.

79. Squirrels. Functions of proteins. Levels of structure.

80. Nitrogen bases of nucleic acids - purines and pyrimidines. Modified nitrogenous bases - antimetabolites (fluorouracil, mercaptopurine).

81.Nucleosides. Nucleoside antibiotics. Nucleotides. Mononucleotides in the composition of nucleic acids and free nucleotides are coenzymes.

82. Nucleic acids. DNA and RNA. Biological significance. Formation of phosphodiester bonds between mononucleotides. Levels of nucleic acid structure.

83. Lipids. Definition. Biological role. Classification.

84.Higher carboxylic acids - saturated (palmitic, stearic) and unsaturated (oleic, linoleic, linolenic and arachidonic).

85. Neutral fats - acylglycerols. Structure, meaning. Animal and vegetable fats.

Hydrolysis of fats - products, meaning. Hydrogenation of vegetable oils, artificial fats.

86. Glycerophospholipids. Structure: phosphatidic acid and nitrogenous bases.

Phosphatidylcholine.

87. Sphingolipids. Structure. Sphingosine. Sphingomyelin.

88.Steroids. Cholesterol - structure, meaning, derivatives: bile acids and steroid hormones.

89.Terpenes and terpenoids. Structure and biological significance. Representatives.

90.Fat-soluble vitamins. General characteristics.

91. Anesthesia. Diethyl ether. Chloroform. Meaning.

92. Drugs that stimulate metabolic processes.

93. Sulfonamides, structure, significance. White streptocid.

94. Antibiotics.

95. Anti-inflammatory and antipyretic drugs. Paracetamol. Structure. Meaning.

96. Antioxidants. Characteristic. Meaning.

96. Thiols. Antidotes.

97. Anticoagulants. Characteristic. Meaning.

98. Barbiturates. Characteristic.

99. Analgesics. Meaning. Examples. Acetylsalicylic acid (aspirin).

100. Antiseptics. Meaning. Examples. Furacilin. Characteristic. Meaning.

101. Antiviral drugs.

102. Diuretics.

103. Means for parenteral nutrition.

104. PABC, PASK. Structure. Characteristic. Meaning.

105. Iodoform. Xeroform.Meaning.

106. Poliglyukin. Characteristic. Value 107.Formalin. Characteristic. Meaning.

108. Xylitol, sorbitol. Structure, meaning.

109. Resorcinol. Structure, meaning.

110. Atropine. Meaning.

111. Caffeine. Structure. Value 113. Furacilin. Furazolidone. Characteristic.Value.

114. GABA, GHB, succinic acid.. Structure. Meaning.

115. Nicotinic acid. Structure, meaning

year, a seminar was held on Improving mechanisms for regulating the labor market in the Republic of Sakha (Yakutia) with international participation, organized by the Center for Strategic Studies of the Republic of Sakha (Yakutia). Representatives of leading scientific institutions abroad, the Russian Federation, the Far Eastern Federal..." took part in the seminar. “Novosibirsk State Academy of Water Transport Discipline code: F.02, F.03 Materials Science. Technology of structural materials Work program for specialties: 180400 Electric drive and automation of industrial installations and technological complexes and 240600 Operation of ship electrical equipment and automation Novosibirsk 2001 Work program compiled by Associate Professor S.V. Gorelov on the basis of the State educational standard of higher professional..." "RUSSIAN STATE UNIVERSITY OF OIL AND GAS named after I.M. Gubkina Approved by the vice-rector for scientific work prof. A.V. Muradov March 31, 2014 PROGRAM of the entrance test in the direction of 06/15/01 - Mechanical Engineering for applicants to graduate school at the Russian State University of Oil and Gas named after I.M. Gubkin in the 2014/2015 academic year. year Moscow 2014 The entrance test program in the direction of 06/15/01 Mechanical Engineering was developed on the basis of the requirements established by the passports of scientific specialties (02/05/04,..." “Appendix 5A: Work program of the special discipline Psychology of Mental Development FEDERAL STATE BUDGET EDUCATIONAL INSTITUTION OF HIGHER PROFESSIONAL EDUCATION PYATIGORSK STATE LINGUISTIC UNIVERSITY Approved by the Vice-Rector for Scientific Work and Development of Intellectual Potential of the University, Professor Z.A. Zavrumov _2012 Postgraduate studies in the specialty 19.00.07 Pedagogical psychology branch of science: 19.00.00 Psychological sciences Department...” “Ministry of Education and Science of the Kabardino-Balkaria State Educational Institution of Secondary Vocational Education Kabardino-Balkarian Automobile and Highway College Approved by: Director of the State Educational Institution of Secondary Professional Education KBADK M.A. Abregov 2013 Training program for qualified workers, employees by profession 190631.01.01 Auto mechanic Qualification Car repair mechanic. Car driver, gas station operator training form - full-time Nalchik, 2013 CONTENTS 1. CHARACTERISTICS..." “is expounded an essence of the ischemic heart disease mathematical model based on traditional view on organs’ blood supply mechanism, that has been worked out in “Medical Scientific Center” joint-venture (Novgorod). According to statistics, currently coronary heart disease (CHD) ranks first in incidence..." “MINISTRY OF TRANSPORT OF THE RUSSIAN FEDERATION FEDERAL AGENCY OF RAILWAY TRANSPORT federal state budgetary educational institution of higher professional education IRKUTSK STATE UNIVERSITY OF TRANSPORTATIONS IRGUPS (IrIIT) APPROVED by Dean of the EMF Pykhalov A.A. 2011 PRODUCTION PRACTICE WORK PROGRAM C5. P Industrial practice, 3rd year. Specialty 190300.65 Railway rolling stock Specialization PSG.2 Cars Graduate qualifications..." “MINISTRY OF EDUCATION AND SCIENCE OF THE RF Federal State Budgetary Educational Institution of Higher Professional Education Tver State University Faculty of Physics and Technology Department of General Physics APPROVED Dean of the Faculty of Physics and Technology B.B. Pedko 2012 Work program of the discipline PHYSICS OF THE ATOMIC NUCLEUS AND ELEMENTARY PARTICLES for 3rd year full-time students Direction 222000.62 - Innovation, profile Innovation Management (by industries and areas..." “MINISTRY OF EDUCATIONAL SCIENCE OF THE RUSSIAN STATE EDUCATIONAL INSTITUTION OF HIGHER PROFESSIONAL EDUCATION VORONEZH STATE UNIVERSITY (GOU VPO VSU) APPROVED Head of the Department of Labor Law Perederin S.V. 01/21/2011 WORK PROGRAM OF ACADEMIC DISCIPLINE B 3.B.13 Land law 1. Code and name of the area of ​​training/specialty: 030900 jurisprudence 2. Profile of training/specialization: jurisprudence_ 3. Qualification (degree) of the graduate: Bachelor of Law_ 4. Form. . ." “The work program was compiled on the basis of the Federal State Educational Standard for Higher Professional Education and taking into account the recommendations of the Approximate Basic Educational Program for the Training of Specialists 130400.65 Mining, specialization 130400.65.10 Electrification and automation of mining production. 1. Goals of mastering the discipline The main goal of the discipline Electrical Machines is to develop students’ theoretical basis on modern electromechanical ... " “Contents I. Explanatory note 3 II. The main results obtained in 2013 during the 6th implementation of the strategic development program III. Appendices 2 I. Explanatory note The goals and objectives of the university’s strategic development program remain unchanged for the entire duration of the program and are gradually achieved in each year of its implementation, ensuring the achievement of the indicators established in the annex to the annotated program. Goal 1 Development of advanced educational technologies Objective..." “Ministry of Education and Science of the Russian Federation Federal Agency for Education of the Russian Federation Vladivostok State University of Economics and Service _ POLITICAL PHILOSOPHY Curriculum of the course in the specialty 03020165 Political Science Vladivostok Publishing House VGUES 2008 BBK 66.2 The curriculum for the discipline Political Philosophy is compiled in accordance with the requirements of the State Educational Standard of Higher Professional Education of the Russian Federation. The subject of the course is politics as a complex social phenomenon, its values ​​and goals, technologies and...” “QUALITY SYSTEM CANDIDATE EXAMINATION PROGRAM IN SPECIALTY p. 2 of 5 05.16.04 FOUNDRY PRODUCTION These questions of the candidate exam in the specialty are compiled in accordance with the program of the candidate exam in the specialty 05.16.04 Foundry, approved by Order of the Ministry of Education and Science of the Russian Federation No. 274 of 08.10.2007. 1 LIST OF QUESTIONS 1. Classification of cast alloys used in mechanical engineering. Basic parameters of alloys: melting point,..." “Considered and adopted at the meeting of the labor Director of the State Autonomous Educational Institution MO SPO MKETI of the college staff V.V. Malkov, protocol No. _ 2013 dated_ Long-term target program Development of the Murmansk College of Economics and Information Technologies for 2013-2015 Murmansk 2013 2 1. College Development Program Passport. Name Long-term target program Development of the Murmansk College of Economics and Information Technology Program for 2013 (hereinafter referred to as the Program) Basis for the Law of the Russian Federation from...” "Ministry of Education and Science of the Russian Federation Federal State Budgetary Educational Institution of Higher Professional Education MOSCOW STATE FOREST UNIVERSITY Faculty of Forestry Department of Artificial Forestry a s h i n a i m a n i z a t i o n i n l / agricultural work APPROVED BY: Rector of the FG B O U V P O M GUL ^J^AJTAEBJUX*PROGRAM OF THE ENTRANCE EXAMINATION TO POST-GRADUATE STUDY Discipline Forestry crops Department Artificial..." “FEDERAL CIVIL AVIATION AGENCY MOSCOW STATE TECHNICAL UNIVERSITY OF CIVIL AVIATION APPROVED Vice-Rector for MMR V.V. Krinitsin _2007. WORKING EDUCATIONAL PROGRAM OF THE DISCIPLINE Thermodynamics and heat transfer, SD.04 (name, code according to GOS) Specialty 160901 Technical operation of aircraft and engines (code according to GOS) Faculty - Mechanical Department - Aircraft engines Course - 3 Form of study - full-time Semester Total amount of training hours for...” “MC45 b USER MANUAL MC45 User Manual 72E-164159-01EN Rev. B January 2013 ii MC45 User's Guide No part of this publication may be reproduced or used in any form or by any electrical or mechanical means without the written permission of Motorola. This includes electronic or mechanical photocopying or recording devices, as well as information storage and retrieval devices...” “The work program was developed on the basis of: 1. Federal State Educational Standard of Higher Professional Education in the direction of bachelor’s training 560800 Agroengineering approved on 04/05/2000 (registration number 313 s/bak). 2. Approximate program of the discipline Fundamentals of Machine Theory, approved on June 27, 2001. 3. Working curriculum, approved by the academic council of the university dated 04/22/13, No. 4. Leading teacher: Ablikov V.A., professor _ Ablikov 06/16/13 Teachers: Ablikov V.A., professor _ Ablikov 06.16.13 Sokht K.A., professor _...” “MINISTRY OF AGRICULTURE OF THE RUSSIAN FEDERATION Federal State Budgetary Educational Institution of Higher Professional Education Moscow State Agricultural Engineering University named after V.P. Goryachkina DEPARTMENT OF MACHINE REPAIR AND RELIABILITY Approved by: Dean of the Faculty of Correspondence Education P.A. Silaichev “_” _ 2013 WORK PROGRAM Specialty 190601 - Automobiles and automotive industry Specialization 653300 - Operation of ground transport Course 6 semester..."

Chemistry- the science of the structure, properties of substances, their transformations and accompanying phenomena.

Tasks:

1. Study of the structure of matter, development of the theory of the structure and properties of molecules and materials. It is important to establish a connection between the structure and various properties of substances and, on this basis, to construct theories of the reactivity of a substance, the kinetics and mechanism of chemical reactions and catalytic phenomena.

2. Implementation of targeted synthesis of new substances with specified properties. Here it is also important to find new reactions and catalysts for more efficient synthesis of already known and industrially important compounds.

3. The traditional task of chemistry has acquired special significance. It is associated both with an increase in the number of chemical objects and properties being studied, and with the need to determine and reduce the consequences of human impact on nature.

Chemistry is a general theoretical discipline. It is designed to give students a modern scientific understanding of matter as one of the types of moving matter, about the ways, mechanisms and methods of converting some substances into others. Knowledge of basic chemical laws, mastery of chemical calculation techniques, understanding of the opportunities provided by chemistry with the help of other specialists working in its individual and narrow fields significantly speeds up obtaining the desired result in various fields of engineering and scientific activity.

The chemical industry is one of the most important industries in our country. The chemical compounds, various compositions and materials it produces are used everywhere: in mechanical engineering, metallurgy, agriculture, construction, electrical and electronic industries, communications, transport, space technology, medicine, everyday life, etc. The main directions of development of the modern chemical industry are: production new compounds and materials and increasing the efficiency of existing industries.

At a medical school, students study general, bioorganic, biological chemistry, as well as clinical biochemistry. Students' knowledge of the complex of chemical sciences in their continuity and interrelation provides greater opportunity, greater scope for research and practical use of various phenomena, properties and patterns, and contributes to personal development.

Specific features of studying chemical disciplines at a medical university are:

· interdependence between the goals of chemical and medical education;

· universality and fundamentality of these courses;

· the peculiarity of constructing their content depending on the nature and general goals of the doctor’s training and his specialization;

· the unity of the study of chemical objects at the micro and macro levels with the disclosure of different forms of their chemical organization as a single system and the different functions it exhibits (chemical, biological, biochemical, physiological, etc.) depending on their nature, environment and conditions;

· dependence on the connection of chemical knowledge and skills with reality and practice, including medical practice, in the system “society - nature - production - man”, due to the unlimited possibilities of chemistry in the creation of synthetic materials and their importance in medicine, the development of nanochemistry, as well as in solving environmental and many other global problems of humanity.

1. The relationship between metabolic processes and energy in the body

Life processes on Earth are determined to a large extent by the accumulation of solar energy in nutrients - proteins, fats, carbohydrates and the subsequent transformations of these substances in living organisms with the release of energy. The understanding of the relationship between chemical transformations and energy processes in the body was realized especially clearly after works by A. Lavoisier (1743-1794) and P. Laplace (1749-1827). They showed by direct calorimetric measurements that the energy released in the process of life is determined by the oxidation of food by air oxygen inhaled by animals.

Metabolism and energy is a set of processes of transformation of substances and energy occurring in living organisms, and the exchange of substances and energy between the organism and the environment. Metabolism of substances and energy is the basis of the life of organisms and is one of the most important specific characteristics of living matter, distinguishing living from non-living. Metabolism, or metabolism, which is ensured by highly complex regulation at different levels, involves many enzyme systems. During the metabolic process, substances entering the body are converted into tissues’ own substances and into final products excreted from the body. During these transformations, energy is released and absorbed.

With the development in the XIX-XX centuries. thermodynamics - the science of the interconversion of heat and energy - it became possible to quantitatively calculate the transformation of energy in biochemical reactions and predict their direction.

Energy exchange can be carried out by transferring heat or doing work. However, living organisms are not in equilibrium with their environment and therefore can be called non-equilibrium open systems. However, when observed over a certain period of time, there are no visible changes in the chemical composition of the body. But this does not mean that the chemical substances that make up the body do not undergo any transformations. On the contrary, they are constantly and quite intensively renewed, as can be judged by the rate at which stable isotopes and radionuclides introduced into the cell as part of simpler precursor substances are incorporated into complex substances of the body.

There is one thing between metabolism and energy metabolism fundamental difference. The earth does not lose or gain any appreciable amount of matter. Matter in the biosphere is exchanged in a closed cycle, etc. used repeatedly. Energy exchange is carried out differently. It does not circulate in a closed cycle, but is partially dispersed into external space. Therefore, to maintain life on Earth, a constant flow of energy from the Sun is necessary. In 1 year, about 10 21 feces solar energy. Although it represents only 0.02% of the total energy of the Sun, it is immeasurably more than the energy used by all man-made machines. The amount of substance participating in the circulation is equally large.

2. Chemical thermodynamics as a theoretical basis of bioenergy. Subject and methods of chemical thermodynamics

Chemical thermodynamics studies the transitions of chemical energy into other forms - thermal, electrical, etc., establishes the quantitative laws of these transitions, as well as the direction and limits of the spontaneous occurrence of chemical reactions under given conditions.

The thermodynamic method is based on a number of strict concepts: “system”, “state of the system”, “internal energy of the system”, “state function of the system”.

Object studying in thermodynamics is a system

The same system can be in different states. Each state of the system is characterized by a certain set of values ​​of thermodynamic parameters. Thermodynamic parameters include temperature, pressure, density, concentration, etc. A change in at least one thermodynamic parameter leads to a change in the state of the system as a whole. The thermodynamic state of a system is called equilibrium if it is characterized by constancy of thermodynamic parameters at all points of the system and does not change spontaneously (without the expenditure of work).

Chemical thermodynamics studies a system in two equilibrium states (final and initial) and on this basis determines the possibility (or impossibility) of a spontaneous process under given conditions in a specified direction.

Thermodynamics studies mutual transformations of various types of energy associated with the transfer of energy between bodies in the form of heat and work. Thermodynamics is based on two basic laws, called the first and second laws of thermodynamics. Subject of study in thermodynamics is energy and the laws of mutual transformations of energy forms during chemical reactions, processes of dissolution, evaporation, crystallization.

Chemical thermodynamics is a branch of physical chemistry that studies the processes of interaction of substances using thermodynamic methods.
The main directions of chemical thermodynamics are:
Classical chemical thermodynamics, which studies thermodynamic equilibrium in general.
Thermochemistry, which studies the thermal effects accompanying chemical reactions.
The theory of solutions, which models the thermodynamic properties of a substance based on ideas about the molecular structure and data on intermolecular interactions.
Chemical thermodynamics is closely related to such branches of chemistry as analytical chemistry; electrochemistry; colloid chemistry; adsorption and chromatography.
The development of chemical thermodynamics proceeded simultaneously in two ways: thermochemical and thermodynamic.
The emergence of thermochemistry as an independent science should be considered the discovery by Herman Ivanovich Hess, a professor at St. Petersburg University, of the relationship between the thermal effects of chemical reactions -- Hess's laws.

3. Thermodynamic systems: isolated, closed, open, homogeneous, heterogeneous. The concept of phase.

System- this is a collection of interacting substances, mentally or actually isolated from the environment (test tube, autoclave).

Chemical thermodynamics considers transitions from one state to another, while some may change or remain constant. options:

· isobaric– at constant pressure;

· isochoric– at constant volume;

· isothermal– at constant temperature;

· isobaric - isothermal– at constant pressure and temperature, etc.

The thermodynamic properties of a system can be expressed using several system state functions, called characteristic functions: internal energyU , enthalpy H , entropy S , Gibbs energy G , Helmholtz energy F . Characteristic functions have one feature: they do not depend on the method (path) of achieving a given state of the system. Their value is determined by the parameters of the system (pressure, temperature, etc.) and depends on the amount or mass of the substance, so it is customary to refer them to one mole of the substance.

According to the method of transferring energy, matter and information between the system under consideration and the environment, thermodynamic systems are classified:

1. Closed (isolated) system- this is a system in which there is no exchange of energy, matter (including radiation), or information with external bodies.

2. Closed system- a system in which there is an exchange only with energy.

3. Adiabatically isolated system - This is a system in which there is an exchange of energy only in the form of heat.

4. Open system is a system that exchanges energy, matter, and information.

System classification:
1) if heat and mass transfer are possible: insulated, closed, open. An isolated system does not exchange either matter or energy with the environment. A closed system exchanges energy with the environment, but does not exchange matter. An open system exchanges both matter and energy with its environment. The concept of an isolated system is used in physical chemistry as a theoretical one.
2) by internal structure and properties: homogeneous and heterogeneous. A system is called homogeneous if there are no surfaces within it that divide the system into parts that differ in properties or chemical composition. Examples of homogeneous systems are aqueous solutions of acids, bases, and salts; mixtures of gases; individual pure substances. Heterogeneous systems contain natural surfaces within them. Examples of heterogeneous systems are systems consisting of substances that differ in their state of aggregation: a metal and an acid, a gas and a solid, two liquids insoluble in each other.
Phase- this is a homogeneous part of a heterogeneous system, having the same composition, physical and chemical properties, separated from other parts of the system by a surface, upon passing through which the properties of the system change abruptly. The phases are solid, liquid and gaseous. A homogeneous system always consists of one phase, a heterogeneous one - of several. Based on the number of phases, systems are classified into single-phase, two-phase, three-phase, etc.

5.The first law of thermodynamics. Internal energy. Isobaric and isochoric thermal effects .

First law of thermodynamics- one of the three basic laws of thermodynamics, represents the law of conservation of energy for thermodynamic systems.

The first law of thermodynamics was formulated in the middle of the 19th century as a result of the work of the German scientist J. R. Mayer, the English physicist J. P. Joule and the German physicist G. Helmholtz.

According to the first law of thermodynamics, a thermodynamic system can undergo work only due to its internal energy or any external energy sources .

The first law of thermodynamics is often formulated as the impossibility of the existence of a perpetual motion machine of the first kind, which would do work without drawing energy from any source. A process occurring at a constant temperature is called isothermal, at constant pressure - isobaric, at constant volume – isochoric. If during a process the system is isolated from the external environment in such a way that heat exchange with the environment is excluded, the process is called adiabatic.

Internal energy of the system. When a system transitions from one state to another, some of its properties change, in particular internal energy U.

The internal energy of a system is its total energy, which consists of the kinetic and potential energies of molecules, atoms, atomic nuclei and electrons. Internal energy includes the energy of translational, rotational and vibrational motions, as well as potential energy due to the forces of attraction and repulsion acting between molecules, atoms and intra-atomic particles. It does not include the potential energy of the system’s position in space and the kinetic energy of the system’s motion as a whole.

Internal energy is a thermodynamic function of the state of the system. This means that whenever the system finds itself in a given state, its internal energy takes on a certain value inherent in this state.

∆U = U 2 - U 1

where U 1 and U 2 are the internal energy of the system V final and initial states, respectively.

First law of thermodynamics. If a system exchanges thermal energy Q and mechanical energy (work) A with the external environment, and at the same time transitions from state 1 to state 2, the amount of energy that is released or absorbed by the system of forms of heat Q or work A is equal to the total energy of the system during the transition from one states to another and is recorded.

Bioorganic chemistry. Tyukavkina N.A., Baukov Yu.I.

3rd ed., revised. and additional - M.: 2004 - 544 p.

The main feature of the textbook is the combination of the medical focus of this chemical course, required for medical students, with its high, fundamental scientific level. The textbook includes basic material on the structure and reactivity of organic compounds, including biopolymers, which are structural components of the cell, as well as the main metabolites and low-molecular bioregulators. In the third edition (2nd - 1991), special attention is paid to compounds and reactions that have analogies in a living organism, the emphasis on highlighting the biological role of important classes of compounds is increased, and the range of modern information of an ecological and toxicological nature is expanded. For university students studying in specialties 040100 General Medicine, 040200 Pediatrics, 040300 Medical and Preventive Care, 040400 Dentistry.

Format: pdf

Size: 15 MB

Watch, download:drive.google

CONTENT
Preface................................... 7
Introduction........................ 9
Part I
BASICS OF STRUCTURE AND REACTIVITY OF ORGANIC COMPOUNDS
Chapter 1. General characteristics of organic compounds 16
1.1. Classification. "................ 16
1.2. .Nomenclature............... 20
1.2.1. Substitute nomenclature........... 23
1.2.2. Radical functional nomenclature........ 28
Chapter 2. Chemical bonding and mutual influence of atoms in organic
connections......................... 29
2.1. Electronic structure of organogen elements...... 29
2.1.1. Atomic orbitals................ 29
2.1.2. Orbital hybridization......................... 30
2.2. Covalent bonds......................... 33
2.2.1. a- and l-Connections......................... 34
2.2.2. Donor-acceptor bonds............ 38
2.2.3. Hydrogen bonds......................... 39
2.3. Conjugation and aromaticity............ 40
2.3.1. Open circuit systems... ,..... 41
2.3.2. Closed-loop systems........ 45
2.3.3. Electronic effects......................... 49
Chapter 3. Fundamentals of the structure of organic compounds....... 51
3.1. Chemical structure and structural isomerism...... 52
3.2. Spatial structure and stereoisomerism...... 54
3.2.1. Configuration................... 55
3.2.2. Conformation................... 57
3.2.3. Elements of symmetry of molecules............ 68
3.2.4. Eianthiomerism............... 72
3.2.5. Diastereomerism............
3.2.6. Racemates................... 80
3.3. Enantiotopy, diastereotopy. . ......... 82
Chapter 4 General characteristics of reactions of organic compounds 88
4.1. The concept of the reaction mechanism..... 88
3
11.2. Primary structure of peptides and proteins........ 344
11.2.1. Composition and amino acid sequence...... 345
11.2.2. Structure and synthesis of peptides............ 351
11.3. Spatial structure of polypeptides and proteins.... 361
Chapter 12. Carbohydrates.................................... 377
12.1. Monosaccharides................... 378
12.1.1. Structure and stereoisomerism......................... 378
12.1.2. Tautomerism..............." . 388
12.1.3. Conformations................... 389
12.1.4. Derivatives of monosaccharides............ 391
12.1.5. Chemical properties............... 395
12.2. Disaccharides................... 407
12.3. Polysaccharides................... 413
12.3.1. Homopolysaccharides............... 414
12.3.2. Heteropolysaccharides............... 420
Chapter 13. Nucleotides and nucleic acids.........431
13.1. Nucleosides and nucleotides.............. 431
13.2. Structure of nucleic acids........... 441
13.3 Nucleoside polyphosphates. Nicotinamide nucleotides..... 448
Chapter 14. Lipids and low-molecular bioregulators...... 457
14.1. Saponifiable lipids......................... 458
14.1.1. Higher fatty acids - structural components of saponifiable lipids 458
14.1.2. Simple lipids................ 461
14.1.3. Complex lipids................ 462
14.1.4. Some properties of saponified lipids and their structural components 467
14.2. Unsaponifiable lipids 472
14.2.1. Terpenes......... ...... 473
14.2.2. Low molecular weight bioregulators of lipid nature. . . 477
14.2.3. Steroids................... 483
14.2.4. Biosynthesis of terpenes and steroids........... 492
Chapter 15. Methods for studying organic compounds...... 495
15.1. Chromatography................... 496
15.2. Analysis of organic compounds. . ........ 500
15.3. Spectral methods............... 501
15.3.1. Electron spectroscopy............... 501
15.3.2. Infrared spectroscopy............ 504
15.3.3. Nuclear magnetic resonance spectroscopy...... 506
15.3.4. Electron paramagnetic resonance......... 509
15.3.5. Mass spectrometry............... 510

Preface
Over the centuries-old history of the development of natural science, a close relationship has been established between medicine and chemistry. The current deep interpenetration of these sciences leads to the emergence of new scientific directions that study the molecular nature of individual physiological processes, the molecular basis of the pathogenesis of diseases, molecular aspects of pharmacology, etc. The need to understand life processes at the molecular level is understandable, “for a living cell is a real the kingdom of large and small molecules, constantly interacting, appearing and disappearing”*.
Bioorganic chemistry studies biologically significant substances and can serve as a “molecular tool” for the versatile study of cell components.
Bioorganic chemistry plays an important role in the development of modern fields of medicine and is an integral part of the natural science education of a doctor.
The progress of medical science and improvement of healthcare are associated with deep fundamental training of specialists. The relevance of this approach is largely determined by the transformation of medicine into a large branch of the social sphere, the field of which includes problems of ecology, toxicology, biotechnology, etc.
Due to the absence of a general course in organic chemistry in the curricula of medical universities, this textbook devotes a certain place to the basics of organic chemistry, which are necessary for mastering bioorganic chemistry. In preparing the third edition (2nd - 1992), the textbook material was revised and brought even closer to the tasks of perceiving medical knowledge. The range of compounds and reactions that have analogies in living organisms has been expanded. More attention is paid to environmental and toxicological information. Elements of a purely chemical nature, which are not of fundamental importance for medical education, have undergone some reduction, in particular, methods for obtaining organic compounds, the properties of a number of individual representatives, etc. At the same time, sections have been expanded to include material on the relationship between the structure of organic substances and their biological acting as the molecular basis for the action of drugs. The structure of the textbook has been improved; chemical material of special medical and biological significance has been included in separate sections.
The authors express their sincere gratitude to Professors S. E. Zurabyan, I. Yu. Belavin, I. A. Selivanova, as well as all colleagues for useful advice and assistance in preparing the manuscript for republication.