Plan of Practical lessons

For I-st Year Foreign Students of the Medical Faculty

(Medical Chemistry)

1 Introduction. Safety in the lab. Periodic system of D.I. Mendeleev. Electron-atomic

structure of elements and ions. The introduction to laboratory safety. Mendeleev Periodic
Law as a background of inorganic chemistry. Electronic structure of atoms and ions. The
main classes of inorganic compounds.
2 Biogenic s-elements, chemical properties, biological role, application in medicine.
5.1. s-elements: electronic structure, oxides, hydroxides, peroxides, superperoxides,
biological meaning of sodium, potassium, calcium, magnesium, strontium.
3 Biogenic -elements, chemical properties, biological role, application in medicine. p-
elements:electronic structure, valency, the oxidation stage; acid-base properties, redox
properties,biological meaning of nitrogen oxide (II), nitrites, phosphorus, arsenic,
oxygen, sulfur, halogens.
4 Biogenic d- elements, chemical properties, biological role, application in medicine.
Chromium as an example of d-elements: electronic structure, oxidation stage, acid-base
properties, red-ox properties
5 The formation of complexes in biological systems. Complexes. The basic rules of Werner
theory (central atom, ligands, coordination number exterior sphere). Classification of the
complexes: by charge of complex ion; by nature of ligands; chelates. Dissociation of
complexes, the constant of instability of complexes. Biological meaning of complexes:
iron-, cobalt-, zinc-containing biocomplexes;
6 Preparation of the solutions and calculation of its concentrations. Mass fraction, molar
concentration, equivalency factor (acids, bases, salts, oxidizing agents, reducing agents).
Molar mass of equivalent; Relationship of various concentration expressions; The
equivalent s law.
7 The basic concepts of volumetric analysis. Neutralization method. Base Standardization.
The basic concepts of neutralization method. Acid standardization: the working
solutions, their preparations; the initial substances; the titration curves, the equivalence
point. The indicators: the points of inflection; methyl orange and phenolphthalein, the
colors in the acid and base medium; the correct selection of the indicators. Application of
base standardization in the clinical analysis.
8 Neutralization method. Acid Standardization. The basic concepts of neutralization
method. Base standardization: preparation of working titrated solutions; initial
compounds; titration curves; the point of inflection, the equivalence point; The indicators:
the points of inflection; methyl orange and phenolphthalein, the colors in the acid and
base mediums; the correct selection of the indicators. Application of base standardization
in the clinical analysis.
9 Acid-base equilibrium in human. pH of biological liquids.
Brensted and Loury theory of acids and bases. Dissociation constant and ion product of
water. Total, active and potential acidity and basicity and their calculations.
Oswald s law of dilution. Calculation of the strong and weak electrolyte pH. Biological
meaning of pH (the value of blood, stomach liquid, urine, intestinal liquid, acidosis and
 alkalosis, the influence of pH values on the activity of enzymes). Indicators: the
points of inflection; methyl orange and phenolphthalein, the standard indicator.
10 Buffer systems, classification and mechanism.
Buffer system. The main physiological buffer systems: their composition, the
examples. Mechanism of buffer system action. Henderson-Hasselbach equation.
Buffer system in organism: an action, ratio of compounds in hydrocarbonate and
phosphate buffer systems. Significance of buffer systems.
11 Buffer capacity. The role of buffer solutions in biological systems.
Buffer capacity. Factors that are influenced on the buffer capacity. Determination of
the buffer capacity by acid and base. What are the buffer capacity values of blood
plasma by acid and base. What is the base supply of blood. Acid-base equilibrium.
12 Colligative properties. Osmosis. Semipermeable membranes (the determination and the
samples). Osmotic pressure. van t-Hoff Law. Osmotic concentration. Isotonic coefficient of
van t Hoff and its relationship with the dissociation degree. Hypotonic, isotonic, hypertonic
solutions and their meaning in medicine. Biological meaning of osmosis.
Membrane equilibrium by Donnan.
13 Module 1 Comprehensive check
14 Thermodynamics, direction of the chemical processes.
Chemical thermodynamics as a branch of the physical chemistry. Thermodynamic
system, types and the examples of the thermodynamic systems, intensive and
extensive parameters of the system. The first law of thermodynamics. Internal
energy of system. Enthalpy. Thermochemical equations. The standard enthalpy of
formation and combustion. Hess s law. Calorimetry. The energetic characteristics of
biochemical processes. Thermochemical calculations for the estimation of the
calorie content in foodstuff and the dietotherapy.
15 Kinetics of biochemical reactions. The rate of the homogeneous and heterogeneous
reactions and its dependence on the concentration. The law of mass action states.
The rate constants. The rate of the reaction. The kinetic equations of zero-, first- and
second-orders reactions. Conception of the reaction mechanism. Molecularity of the
reaction. The dependence of the reaction rate on the temperature. Vant-Hoff s rule.
The characteristic properties of the temperature coefficient for the biological
processes. Collision theory. Activation energy. Arrhenius equation. Transition states.
16 Chemical equilibrium. Solubility. Reversible and irreversible chemical reactions.
Chemical equilibrium. Thermodynamic conditions of equilibrium. The constant of
the chemical equilibrium and its expression. The shift of chemical equilibrium
changing temperature, pressure and concentration. Le Chatelier s principle.
Solubility and precipitation reactions. The conditions of solubility and
precipitation. Solubility product. The role of the heterogeneous equilibrium (in the
presence of the salts) in the general homeostasis of human organism.
17 Potentiometry. Galvanic cell. Determination, its structure, the schema. Electrode potential.
The half-cells. Nernst s equation, Standard electrode potential. Reference electrodes:
hydrogen electrode, saturated calomel electrode. Structure and their standard electrode
potentials. Electrodes for pH measurements: hydrogen, glass electrodes, their structure,
schema of the electrodes. Electro motive force. Concentrated galvanic cell, the
 principle, the schema, the equation. Determination of pH using hydrogen-
hydrogen, saturated calomel-hydrogen, saturated calomel-glass galvanic cells,
the schema, equation of pH calculation. Measurement of pH using pH meter.
18 Determination of redox potentials. Redox systems (determination, the examples).
Mechanism of redox potential appearing. Nernst equation, the depending factors
of redox potential, the standard redox potential. Biological meaning of the redox
system. Diffusion and membrane potentials.
19 Sorption of biological active substance at the interface of liquid-gas. Surface
tension and surface energy. Surface phenomena at the interface liquid-gas: the
structure of the surface layer, surface tension. Gibbs equation, surface activity.
Surface active and inactive agents. Duclo-Traube s rule. Methods of surface
tension determination. Surface tension of biological systems.
20 Sorption of biological active substance at the interface of solid-liquid.
Basic aspects of adsorption. Determinations: sorption, physical and chemical adsorption,
absorption, the adsorbents and adsorbates. Adsorption at the surface of the solid.
Isotherms and equation of Langmur, BET, Freundlich. The value of sorption.
Hemosorption. Enterosorption. Adsorption significance for the living organisms.
21 Ion exchange. Chromatography. The adsorption of the electrolytes (selective and
ion exchange). Panet- Phayance rule. The natural and synthetic ion-exchangers.
The role of ionic exchange in the processes of vital functions. Adsorption therapy.
Chromatography. The principles of the method. Classification of the
chromatographic analysis: by the phase stage; by techniques; by distribution
mechanism. Adsorption chromatography, ion-exchange chromatography and
partition chromatography. Application of chromatography in biology and medicine.
22 Preparation, purification and properties of colloidal solutions. Definition of
colloids. Synthesis of the colloidal systems. Purification of colloids. Artificial
kidney. Micelle structure. Panet-Phayance rule. Colloidal solutions in medicine.
Classification of the colloids: by particle size, dispersed and dispersing phases,
interfacing interaction. Molecular-kinetic properties of colloids (Brownian
movement, diffusion in sols, osmotic pressure) Optical properties of colloids.
Tyndall s effect. Electrophoresis and its application in medical practice.
23 Coagulation of colloidal solutions. Colloidal stability. Kinetic and aggregative
stability of sols, the stability factors. Coagulation and the factors influenced on the
coagulation. Coagulation mechanism. Schulz-Hardy s rule. Coagulation ability of
electrolytes. Reciprocal coagulation. Coagulation concentration. Colloidal
stability. Coagulation application in the water purification process.
24 Properties of biopolymers. Isoelectric point of proteins. Polymers. Isoelectric state
and isoelectric point of the proteins. Protection action of proteins, protection number,
biological meaning. Swelling of polymers (definition, mechanism, factors). The fixed
water, properties and biological meaning. The stability of polymers. Factors of
stability. Gelatinization of polymer solution, mechanism, factors, biological meaning.
Galantines, reaction in galantines, biological meaning.
25 Module 2 Comprehensive check
 Plan of Practical lessons
For I-st Year Foreign Students of the Medical Faculty
(Bioorganic Chemistry)

1 Nomenclature, isomerization, electronic structure of chemical bonds.

Main aspects of the International (systematic) nomenclature IUPAC. Space isomerization
of bioactive compounds: cys trans isomers, enantomers, conformation isomerization
(definition, examples, meaning for biological processes). Distribution of electron density
in organic molecules: electron inductive and mesomeric effects. Classification of organic
compounds according to the structure of carbon skeleton and the nature of functional
groups. Hybridization of the carbon atom, electronic structure of its chemical bonds.
Electronegativity of chemical elements.
2 Reactivity of alkanes, alkenes, arenes. The classsification of chemical reactions by
mechanism. The types of chemical bond breakage, free radicals, nucleophilic and
electrophilic particulares (defenition, examples). The mechanism of substitution radical
reaction (SR) beside the carbon atom in alkanes the mechanism of halogenation reaction,
biological meaning of free radicals. The mechanism of addition electrophilic reaction in
alkenes ( ); mechanism of halogenation reaction, biological meaning. The mechanism
of substitution electrophilic reaction in benzene (SE); mechanism of halogenation
reaction, biological meaning. I and II order substituents. The influence of functional
group on reactivity of arenas. The formulas of ethane, propane, butane, hexane, benzene,
methylbenzene, benzoic acid and their isomers.
3 Reactivity of halides, alcohols, phenols and amines. Acidity and basicity according to
Brensted and Loury. The dependence of the acidity of alcohols, phenols on carbon chain
length and on type of substitute. The dependence of the basicity of amines and phenols
on carbon chain length and on type of substitute. The mechanism of nucleophilic
substitution (SN) beside the non-saturated carbon atom in halogenated organic
compounds. Interaction with a base, ammonia, amines (formation of primary, secondary,
tertiary amines and quaternary bases). The mechanism of nucleophylic substitution (SN)
in alcohols. Interaction with a hydrogen chloride. The mechanism of elemination reaction
of alcohols. Formulas to know: propanol, isopropanol, butanol, isobutanol, phenol and its
derivative; primary, secondary, tertiary and quaternary bases, colamine, aniline.
4 Reactivity of aldehydes and ketons. Electronic structure of the oxo-group.The mechanism
of nucleophilic addition reaction ( N) to the trigonal carbon atom. Interaction with
alcohols: mechanism of formation of half-acetalles and acetalles. Their biological
meaning. Interaction with amines: mechanism of addition-detachment. Biological
meaning of imines. Aldolic condensation: mechanism of alkaline catalysis; biological
meaning (synthesis of the citrate in organism (citrate acid) and neuraminic acid).
Oxidation and reduction of aldehydes and ketones. The examples of these reactions in
human organism.
5 Nucleophilic substitution in carboxylic acids. The electronic structure of the carboxyl
group and carboxylate anion. Acidity of the carboxylic acids. The influence of the
different substituents on acidity of carboxylic acids. Salts of carboxylic acids, the
 mechanism of their formation. The formation of salts of carboxylic acids in human
organism. Mechanism of nucleophilic substitution (SN) beside the trigonal carbon atom:
mechanism of the ester and thioethers formation; mechanism of acidic and alkaline
hydrolysis of esters; Formation and hydrolysis of esters and thioethers in human organism.
Synthesis of biological active substances with acetyl-KoA in human organism.
6 Lipids and phospholipids. Lipids, saponificated lipids (definition). Higher fatty acids:
saturated and unsaturated, spatial structure of unsaturated acids, chemical characteristics.
Fats as triacylglycerols, their composition, structure, classification, chemical properties
(hydrolysis, iodine number, peroxide oxidation). Phosphoglycerols: composition, structure
of phosphatidylcholine, phosphatidylcolamine, phosphatidylserine and their biological
meaning. Non-saponificated lipids. Structure of cholesterine, bile acids
7 Heterofunctional compounds. Hydroxo-acids (lactic, tartratic, citric, - oxybutyric,
malic acids), properties, specifical reactions: appearance in the organism and
biological meaning of these compounds. Oxo-aicds (pyruvic, aceto-acetic, oxalo-
acetic acids). Keto-enole tautomery. Chemical properties, reaction of
decarboxylation. Phenol acids and their derivatives. Uses of salicylic acid and its
derivatives (Sodium salicylates, methylsalicylate, salol, acetylsalicyllic acid).
8 Amino acids: definition, composition, structure. Acid-base properties of amino acids.
Chemical reactions of amino acids by carboxyl-group: ester and halogen anhydrides
formation. Biological meaning of these reactions. Chemical reactions of amino acids by
amino-group: N-acyl derivatives formation, interaction with nitrite acid, formaldehyde,
phenylisothyocyanate. Biological significance of these reactions. Decarboxylation of
amino acids and biological meaning of biogenic amines formation.
9 Proteins. Definition, protein s molar mass. Analysis of peptides and proteins: determination
of amino acidical order in proteins by Edman s method. Peptide and protein synthesis
using protection and activation of functional groups. The first decoded and synthesised
proteins and peptides: insulin, vasopressin, oxytocin; their composition, structure, biological
meaning. Formation and properties of peptide bond. Physical and chemical properties of
peptides (amphotericity, amphion, salts; isoelectric state (IES), isoelectric point (IEP).
Levels of protein structural organisation: primary, secondary, tertialy, quaternary. Types
and nature of chemical bond. Methods of extraction, separation and purification of proteins.
Determination methods of protein s molar mass.
10 Monosaccharides. Carbohydrates. The classification of carbohydrates. Glucose:
non-cyclic form: Fisher projection, D- and L-configuration; cyclic form (pyranose
and furanose): Heuorse`s projection, and - anomers; conformation: - D and - D
configuration. Tautorotation (birotation). Chemical properties of glucose:
formation of helates, and N glycosides, alkylation, acetylation. The formules to
know: glucose, fructose, ribose, desoxyribose and their derivatives (glycone,
glycarone, glycurone acids, glycosamines, phospho esters). Ascorbic acid,
structure, biological meaning. Qualitative reactions on monoatomic alcohols and
aldehyde group. Qualitative reaction on fructose (Selivanov s reaction).
11 Oligo- and Polysaccharides. Disaccharides. Disaccharides classification according to
their ability to oxydative-reductive reactions. Saccharose structure, lactose structure:
reductive abilies and oxy-groups (helates appearance, alkylation, acetylation).
Homopolysaccharides: starch, glycogen, cellulose, dextranes: composition, structure,
primary and secondary structure, chemical properties, biological meaning.
 Starch hydrolysis, qualitative reaction for starch determination.
12 Heterocyclic compounds. Heterocycles classification according to the cycle size, quantity
and the nature of heteroatoms. Pentamerous heterocycles with one heteroatom (pyrrole).
Benzopyrrole (indole) as a part of tryptophan and its metabolites (tryptamine, serotonin)
and toxic compounds (skatole, indole). Pentamerous heterocycles with two heteroatoms
(pyrazole). Pyrazole derivatives as medical preparations. Hexamerous heterocycles with
one (pyridine) and two (pyrimidine) heteroatoms, their main properties. Pyrimidine nitrogen
bases and their tautomery. Heterocyclic compounds (purine) and its derivatives (nitrogen
bases of nucleic acids, uric acid). Main properties, tautomerism.
13 Nucleic acids, structure, composition and biological significance. Structural
components of nucleic acids, chemical properties. Qualitative reaction. Nucleosides:
definition, structure, types of linkages, nomenclature, properties. Nucleotides:
difinition, structure, types of linkages, nomenclature, properties. Nucleoside
phosphate, the meaning of ATP. The role of nucleotides in the formation of
coenzymes. RNA and DNA: structure, types, types of linkages, complementary
pairs. Biological significance of nucleic acids. DNA duplex. Complementary pairs.
14 Practical skills: Theoretical essential principles of structure and reactivity of
bioorganic .
15 Module 3 Comprehensive check