МІНІСТЕРСТВО ОХОРОНИ ЗДОРОВ’Я УКРАЇНИ 

ХАРКІВСЬКИЙ НАЦІОНАЛЬНИЙ МЕДИЧНИЙ УНІВЕРСИТЕТ 

 

 

 

 

 

 

CARBOHYDRATES: MONOSACCHARIDES. STRUCTURE AND 

FUNCTIONS OF DI- AND POLYSACCHARIDES. 

Methodical instructions for 1
st
 year students’ self-work 

in Biological and bioorganic chemistry 

 

 

 

 

 

ВУГЛЕВОДИ: МОНОСАХАРИДИ. СТРУКТУРА І ФУНКЦІЇ ДИ- ТА 

ПОЛІСАХАРИДІВ 

Методичні вказівки для самостійної роботи студентів 1-го курсу 

з біологічної та біоорганічної хімії 

 

 

 

 

 

Затверджено 

Вченою радою ХНМУ 

Протокол №     від             2018 

 

 

 

 

 

 

 

 

 

 

 

 

Харків 2018 



 2 

Carbohydrates: monosaccharides. Structure and functions of di- and 

polysaccharides: methodical instructions for 1
st
 year students’ self-work / 

compiled by A.O. Syrovaya, V.N. Petyunina, V.O. Makarov et al. – 2
nd

 

edition, revised, corrected and expanded – Kharkiv: KhNMU, 2018. – 28 p. 

 

Compiled by: 

A.O. Syrovaya, 

V.N. Petyunina, 

V.O. Makarov, 

S.V. Andreeva, 

L.V. Lukianova, 

S.N. Kozub, 

T.S. Tishakova, 

O.L. Levashova, 

E.V. Savelieva, 

N.N. Chalenko, 

O.S. Kalinenko, 

O.A. Zavada, 

N.V. Kopoteva, 

M.A. Vodolazhenko 

H.A. Chistiakova 

 

Вуглеводи: моносахариди. Структура і функції ди- та полісахаридів: 

метод. вказ. для студентів 1 курсу / уклад. Сирова Г.О., Петюніна 

В.М., Макаров В.О. та ін. – 2-е вид., переробл., випр., доп. – Харьков: 

ХНМУ, 2018. – 28 с. 

 

Укладачі: 

Г.О. Сирова, 

В.М. Петюніна, 

В.О. Макаров, 

С.В. Андрєєва, 

Л.В. Лук’янова, 

С.М. Козуб, 

Т.С. Тішакова, 

О.Л. Левашова, 

О.В. Савельєва, 

Н.М. Чаленко, 

О.С. Каліненко, 

О.О. Завада, 

Н.В. Копотєва, 

М.О. Водолаженко 

Г.О. Чистякова 



 3 

Subject I “Carbohydrates: monosaccharides. Structure and functions of di- and 

polysaccharides” 

 

1. Number of hours – 4. 

 

2. Material and methodological support. 

a) Tables: 

- Graph structure of the subject; 

- Classification of carbohydrates; 

- Glycosidic ОН-group; 

- Ring-chain tautomerism; 

- Tautomeric transformations of D-glucose; 

- Disaccharides (lactose, maltose, sucrose); 

- Composition of vegetable starch; 

- Pentoses (ribose, arabinose, xylose); 

- Ascorbic acid; 

- Heparin Гепарин; 

- Glycolysis Гліколіз; 

- Chondroitin-6-sulfate; 

- Hyaluronic acid. 

b) Reactants and equipment: rack with test tubes, graduated pipets, burner; 

solutions: 0,5% glucose, fructose, starch, 1% sucrose, maltose, lactose, 5% CuSO4, 

10% NaOH, concentrated HCl, 1 drop of diluted I2 solution. 

 

Educational literature: 

1. Biological and Bioorganic chemistry: in two books: Textbook. Textbook 1. 

Bioorganic chemistry / B.S. Zimenkovsky, V.A.Muzyhenko, I.V. Nizhenkovska, 

G.O. Syrova; edited by B.S. Zimenkovsky, I.V. Nizhenkovska. – K.: AUP 

―Medicina‖, 2017. – 288 p. 



 4 

2. Fundamentals of bioorganic chemistry: manual / A. O. Syrovaya, E. R. 

Grabovetskaya, V. N. Petiunina. – Kharkiv : KhNMU, 2016. – 191 p. 

3. Carbohydrates: oligo- and polysaccharides: Methodical instructions for 1
st
 year 

students’ / compiled by A.O. Syrovaya, L.G. Shapoval, V.N. Petyunina, E.R. 

Grabovetskaya, N.M. Tkachuk, V.A. Makarov, S.V. Andreeva, S.A. Nakonechnaya, 

L.V. Lukyanova, R.O. Bachinsky, S.N. Kozub, T.S. Tishakova, O.L. Levashova, 

N.V. Vakulenko, N.N. Chalenko. – Kharkiv: KhNMU, 2013. – 30 p. 

4. Carbohydrates: monosaccharides. Structure and functions of di- and 

polysaccharides: methodical instructions for 1
st
 year students’ self-work / 

compiled by A.O. Syrovaya, V.N. Petyunina, V.O. Makarov et al. – 2
nd

 edition, 

revised, corrected and expanded – Kharkiv: KhNMU, 2018. – 28 p. 

5. Text of Lectures. 

 

3. Substantiation of the subject. 

Carbohydrates are probably the most abundant and widespread organic 

substances in nature, and they are essential constituents of all living things. They 

participate in metabolic and energy-releasing processes in the human and animal 

body. Carbohydrates as main components of food provide energy for life functions. 

Carbohydrates are the precursors for synthesis of other compounds in the body, for 

example, fats, amino acids, steroids. 

Carbohydrates and their derivatives are used in applied medicine: 40% solution of 

glucose, glycosides (for example, digitalis – as cordial agent and dextran as blood 

substitute). 

Disorders of carbohydrate metabolism are characteristic for many diseases such as 

diabetes mellitus, lactose and fructose intolerance, galactosemia, glycogen storage 

diseases, damages of liver and nervous system. 

Knowledge about the structure of mono- and polysaccharides and their properties 

can be used in practice of future doctors and in medico-biological investigations. 



 5 

4. The purpose of the subject: 

1. To know the classification of monosaccharides by number of carbon atoms and 

functional groups, depending on the ring size and location hemiacetal hydroxyl. 

2. To study the most stable conformation of the hexoses. 

3. To learn the properties associated with the existence of a hemiacetal (glycoside) 

hydroxyl in monosaccharide molecules 

4. To be able to illustrate properties of monosaccharides linked to the presence of 

carbonyl and hydroxyl groups (oxidation, reduction, the formation of ethers, esters, 

hexoses epimerization in an alkaline medium). 

5. To know the monosaccharide composition, structure, conformation of the most 

important disaccharides (maltose, lactose, cellobiose, sucrose). 

6. To learn Find out the fractional composition of starch, linear and spatial structure 

of amylose and amylopectin and glycogen – glycogen. 

7. To learn the basic chemical properties of starch: hydrolysis, the compound 

inclusion.  

8. To know the composition and structure of the major heteropolysaccharides: 

hyaluronic acid, heparin, chondroitin sulfate. 

 

5. Practical skills: 

1. To be able to predict the properties of important monosaccharides. 

2. To be able to carry out the reaction for monosaccharides. 

3 To be able to predict the properties of the polysaccharides. 

4. To be able to carry out qualitative reaction for the polysaccharides. 

 



 6 

 

 

 

6. Graph structure of the subject. 

 

Carbohydrates 

Monosaccharides 

Aldoses 

Tetroses 

Trioses 

Pentoses 

Hexoses 

Ketoses 

Tetroses 

 
Pentoses 

Trioses Hexoses 

Homopolysaccharides 

High-molecular 

Polysaccharides 

Heteropolysaccharides 

Oligosaccharides 

Non-reducing 

Sucrose 

Reducing 

Maltose 

Starch Hyaluronic acid 

Chondroitinsulfates 

Acyclic Cyclic 

Oxidation 

Reduction 

Утворення 

озазонів 

Epimerization  

Ethers 

formation 

Esters 

formation 

 

Glycoside 

formation 



 7 

 

 

 

 

 

7. Plan of students’ work. 

№ Stages Time Training and visual aids Location 

1. Motivational 

characteristics and plan of 

the subject. Answers to the 

students’ questions 

25 min  

C
la

ss
 r

o
o
m

 

2. Control of students' 

knowledge baseline 

20 min Tests for initial control 

3. Students’ knowledge 

correction by solving of 

educational tasks 

(individual work) 

60 min Methodical instruction for 

students, lecture notes, reference 

data, posters. Manuals, reference 

materials, tables. 

4. Laboratory work 35 min Reactants and equipment 

5. Control of knowledge 25 min Tests for control 

6. Analysis and conclusions. 

Home work 

15 min  

 



 8 

8. Tasks for self-work: 

 

- list of questions to be study: 

 

1. Classification of carbohydrates. Isomerism. Tautomeric forms of 

monosaccharides. Mutarotation. 

2. Chemical reactions of monosaccharides with the participation of carbonyl-

group: oxidation-reduction reactions (qualitative reactions for the detection of 

aldehyde group). 

3. Glycoside formation, their role in the structure of oligo- and 

polysaccharides, nucleosides, nucleotides and nucleic acids. Phosphate esters of 

glucose and fructose, their significance in carbohydrate metabolism. 

4. Ascorbic acid as derivative of hexoses, biological role of vitamin С. 

5. Oligosaccharides: structure, properties. Disaccharides (sucrose, lactose, 

maltose), their biomedical significance. 

6. Polysaccharides. Homopolysaccharides: starch, glycogen, cellulose, 

dextran – structure, hydrolysis, biomedical significance. Qualitative reaction of 

starch. 

7. Heteropolysaccharides: determination, structure. Structure and biomedical 

significance of glucosaminoglycans (mucopolysaccharides) – hyaluronic acid, 

chondroitin sulfates, heparin. 



 9 

Teaching tasks and examples of their solution 

 

Task №1. What isomers are characteristic for monosaccharides? What is the 

difference between optical isomers? 

 

Example of solution: Pentoses and hexoses are the most common in nature. Usually 

they have unbranched chains, so quantity of the isomers is expected to be quite small. 

However,  monosaccharides contain several asymmetric carbon atoms and therefore 

they show optical isomerism. Thus, aldohexoses have four asymmetric carbon atoms 

and 16 optical antipodes. They are divided into eight pairs of D-and L-hexoses which 

differ in the arrangement of substituents around asymmetric carbon atoms and have 

the same properties, except for sign of rotation. 

 

C

C

C

C

C

CH
2
OH

O

H

H

H

H

H

OH

OH

OH

C

C

C

C

C

CH
2
OH

O

H

H

H

H

H

OH

OH

C

C

C

C

C

CH
2
OH

O

H

H

H

H

H

OH

OH

НО НО

НО

НО

НО

*

*

*

*

*

*

*

*

*

*

*

*

1

2

3

4

5

6

1

2

3

4

5

6

1

2

3

4

5

6

 

 

Isomers which have different arrangement of hydroxyl groups at some chiral 

centers have not only different optical activity but also differ in some physical and 

chemical properties and named differently (glucose, galactose, mannose, etc.).  

The aldehyde and keto-formulas clearly explain the reactions of these 

substances. However, there are some properties which can not be explained by the 

structure of these formulas. Aldoses do not give some characteristic aldehyde 



 10 

reactions. Glucose, e.g., under normal conditions does not produce coloration with 

Schiff’s reagent. At the same time, some reactions (formation of glycosides) can not 

be explained by oxo forms. 

 

Task №2. What is the essence of tautomeric transformations of 

monosaccharides, what is their influence on the chemical properties? 

 

Example of solution: Aldehyde or keto structure is one of tautomeric forms of 

monosaccharides and most of saccharides exist as cyclic tautomeric forms which are 

internal hemiacetals of polyhydric aldehydes and ketones. 

Tautomeric transition of aldehyde or ketone form into cyclic one is the 

formation of internal hemiacetal due to displacement of hydrogen atom from 

hydroxyl group at the fifth or fourth carbon atom to a carbonyl group. As a result the 

carbon atoms become connected through oxygen with the formation of six- or five-

membered ring: 

 

CH
2
OH

O

H

H

H

H

H

OH

OH

HO

OH C

CH
2
OH

H

H

H

H

H

OH

HO

O

OH

C

CH
2
OH

O

H

H

H

H

H

OH

OH

HO

HO

OH

-D-Glucose(I) D-Glucose -D-Glucose(II)

C

 

 

The formation of the cyclic form is accompanied by formation of new hydroxyl 

group which is absent in the open-chain form. It is called hemiacetal hydroxyl group. 

) 



 11 

Its properties differ from the other hydroxyl groups because of two reasons. First of 

all, it is in equilibrium with the carbonyl group and second of all, it is bound with 

carbon connected to oxygen of the cycle which attracts electronic density. Carbon 

atom which is linked to a hemiacetal hydroxyl group is asymmetric, thus the 

existence of two cyclic isomers is possible. They are named as - and -anomers - 

the forms in which the location of hemiacetal hydroxyl group is the same as the 

location of hydroxyl at the asymmetric carbon atom which defines belonging of the 

saccharide to D- and L-series. 

English chemist Haworth offered to represent cyclic forms of monosaccharides 

in the form of regular polygons that lie perpendicular to the plane of the figure: 

 

CH
2
OH

H
HH

H

H
OH

OH

OH H

OH H

HO

OH

CH
2
OH

CH
2
OH

H
OH

O
O *

*
1

23

4

5

 

-D-glucopyranose   -D-fructofuranose 

 

Cyclic monosaccharides can exist in the same conformations as other cycles, which 

consist of tetragonal carbon atoms, e.g., chair conformation. 

 

OH

HO

HO

CH
2
OH

O

O

H

 

 



 12 

Task №3. What biologically important products can be obtained by oxidation 

and reduction of glucose? 

 

Example of solution: The presence of different functional groups in 

monosaccharides, as well as their ability to tautomeric transformations results in high 

reactivity and variety of chemical properties of monosaccharides. They easily enter 

oxidation reactions. Products depend on the strength of the oxidizing agents and the 

pH. 

Glucose on reaction with bromine water in neutral medium is oxidized into 

hydroxy acid with same number of carbon atoms: 

 

C C C C C C C C C C C C

H

H

H H HOH

OH OHOH OHH

O

H

H H HOH

OHOH OHH

O

OH

HOBr

H

H Br

HO

+ + H

 

D-glucose D-gluconic acid 

 

Stronger oxidizing agents (e.g., concentrated nitric acid) oxidize not only 

aldehyde group but also the primary alcohol group into carboxyl groups. The 

products are dibasic hydroxy acids: 

 

C C C C C C C C C C C C

H

H

H H HOH

OH OHOH OHH

O

H

O  
H H HOH

OH OH OHH

O O

OHHO
 

D-glucose     D-glucaric (saccharic) acid 

 

The most pronounced transformations of monosaccharides take place in 

alkaline medium. Interaction with the ammoniacal silver nitrate or copper(II) 



 13 

hydroxide results in breaking of the carbon chain with formation of mixture of 

different hydroxy acids. 

Reduction with hydrogen in the presence of metallic nickel converts 

monosaccharides into polyhydric alcohols: 

 

C C C C C C C C C C

H

H

H H HOH

OH OHOH OHH

O

H

H H HOH

OHOH OHH
Ni

HOH
2
C CH

2
OH

H2

 

D-glucose     D-glucitol (sorbitol) 

 

Glucose is reduced into hexatomic alcohol sorbitol, which is used as a sugar 

substitute for diabetics. 

 

Task №4. Write the reaction of monosaccharides with phosphoric acid. 

 

Example of solution: The alcoholic hydroxyls of glucose participate in the formation 

of ethers with alcohols and esters with acids. Phosphoric acid esters of 

monosaccharides are of great biological importance. 

 

O

H

OHH

OH

OH

H

H

OH

H

CH
2
OH

O

H

H

OH

OH

H

H

OH

H

H
3
PO

4

CH
2
OH

O P

O

OH

OH

+ + H2O

 

-D-glucopyranose 1-phosphate--D-glucopyranose 

 

Phosphate formation is the first step of the biochemical transformations of 

monosaccharides. 



 14 

Task №5. What transformations of monosaccharides occur in alkaline 

medium? 

 

Example of solution: In alkaline medium monosaccharides undergo isomerization 

via the formation of the enol form: 

 

C
O
..

H

CH OH

C

C

C

CH
2
OH

HHO

OHH

OHH

C
O

H

C OH

C

C

C

CH
2
OH

HHO

OHH

OHH

H

C

C

C

C

CH
2
OH

HHO

OHH

OHH

CH
2
OH

O

 

D-glucose Endiol form D-fructose 

 

Isomerization of monosaccharides and their derivatives takes place in 

important biochemical transformations. 

 

Task №6. What transformations of monosaccharides take place under the 

action of microorganisms? 

Example of solution: Conversion of monosaccharides by the action of 

microorganisms is called fermentation. Depending on the process conditions and the 

type of microorganisms there are several types of fermentation: 

 

                     2С2Н5ОН+2СО2                                     alcohol 

С6Н12О6            2СН3-СНОН-СООН                         lactic 

                      СН3 – (СН2)2 – СООН+2СО2+2Н2      butyric 

 



 15 

The highest reactivity of the hemiacetal hydroxyl group as compared to other 

hydroxyl groups allows, under certain conditions (boiling of glucose in alcohol 

solution containing 2% of dry hydrochloric acid), to obtain acetals of saccharides – 

glycosides. 

O

H

OHH

OH

OH

H

H

OH

H

CH
2
OH

O

H

H

OH

OH

H

H

OH

H

CH
2
OH

O

HO CH
3

CH
3

+ + H2O

 

-D-glucopyranose methyl--D-glucopyranoside 

 

Some natural glycosides serve as medicines, e.g., cardiac glycosides. 

 

Task №7.What is the biological role of monosaccharides? 

 

Example of solution: Ribose and deoxyribose are of great biological 

importance. They are the components of ribonucleic and deoxyribonucleic acids.  

The most common aldohexose is glucose. It is also known as grape sugar, as it 

is contained in the grape juice. Glucose is also contained in other sweet fruits. There 

are about 0.1% of glucose in blood. 

Fructose is the representative of ketohexoses. This one is the sweetest of all 

carbohydrates. In large quantity it is found in honey. 

 

Task №8. Give the structure of the amino sugars. Characterize their properties. 

 

Example of solution: Derivatives of monosaccharides obtained by substitution of 

alcoholic hydroxyl with amino group are called amino saccharides. They possess 

strong reducing properties. Residues of amino saccharides enter the composition of 



 16 

certain polysaccharides. 

O

H

OHH

OH

OH

H

H

H

CH
2
OH

O

H

H OHOH

H

H

OH

H

CH
2
OH

NH
2 NH

2  

2-deoxy-2-amino--D-galactopyranose 2-deoxy-2-amino--D-glucopyranose 

(galactosamine) (glucosamine) 

 

Task №9. Which polysaccharides are called oligosaccharides? Give examples. 

Characterize bonds between the monosaccharide units and chemical properties. 

 

Example of solution: All polysaccharides can be regarded as anhydrides of simple 

sugars which are obtained by removal of one or more molecules of water from two 

and more monosaccharides molecules. Polysaccharides are divided into two 

subgroups: oligosaccharides - relatively low-molecular weight carbohydrates, which 

give a small number of molecules of monosaccharides on hydrolysis (name is derived 

from the Greek "olіgos" - few) and high-molecular weight polysaccharides which are 

composed of hundreds and thousands of monosaccharide residues. 

Oligosaccharides exhibit a number of properties which are similar to those of 

simple carbohydrates: they are highly soluble in water and have a sweet taste. 

Disaccharides are the most important. They all are glycosides, that is, a 

molecule of water is released from two molecules of monosaccharides with 

obligatory participation of hemiacetal (glycosidic) hydroxyl group. Hydroxyl group 

of the second molecule which participates in the formation of a glycosidic bond may 

be either alcoholic or hemiacetal one. In the first case the disaccharide molecule has 

one hemiacetal hydroxyl, and therefore such compounds have similar properties with 



 17 

monosaccharides, i.e. they can be easily oxidized, so they are known as reducing 

disaccharides. 

If the disaccharide molecule is formed involving hemiacetal hydroxyls of both 

monosaccharides they are known as non-reducing disaccharides. 

The reducing disaccharides are able to tautomerism due to the presence of 

hemiacetal hydroxyl group in the molecule. Therefore, they enter chemical reactions 

that are characteristic for monosaccharides (oxidation with silver oxide, osazones 

formation, etc.). The most important reducing disaccharides are maltose (malt sugar) 

and lactose (milk sugar). 

 

O

CH
2
OH

H

H

H

H
H

OH

OH
OH

O

CH
2
OH

H

H

H
H

OH

OH

H

OH

O

O

CH
2
OH

H

H

H
H

OH

OH
OH

H

OH

O

CH
2
OH

H

H

H
H

OH

OH
OH

H

OH
1 4

+
H2O, H+

 

-maltose -D-glucopyranose  -D-glucopyranose 

 

In maltose molecule two residues of -D-glucose are linked by 1,4-glycosidic 

bond; lactose consists of residues of D-galactose and D-glucose in β-form. 

Sucrose is an example of non-reducing sugars. It consists of residues of D-

glucose and D-fructose. Sucrose has no free glycosidic hydroxyl, so it can not be 

transformed into the open carbonyl form and therefore does not reduce silver oxide 

and copper(II) hydroxide. Like all polysaccharides, sucrose is capable of hydrolyzing 

and exhibits the properties of polyols. 

 



 18 

Task №10. Which compounds are called homopolysaccharides? 

 

Example of solution: Polysaccharides are high-molecular weight substances, which 

are composed of hundreds or thousands of monosaccharide residues. These residues 

may be identical (homopolysaccharides) or different (heteropolysaccharides). Starch 

and cellulose are the main homopolysaccharides. These polysaccharides are 

hydrolyzed into glucose. The composition of both compounds is expressed as 

(C6H10O5)n. Glucose residues are joined by glycosidic linkages in the long chains, 

wherein one molecule provides its hemiacetal hydroxyl and second molecule 

provides its alcoholic hydroxyl group: 

 

O

CH
2
OH

H

H

H

H
H

OH

OH
O

O

CH
2
OH

H

H

H
H

OH

OH
O

O

CH
2
OH

H

H

H

H

OH

OH

O

CH
2
OH

H

H

H
H

OH

OH
O

H H

O

H

O1 4

 

amylose 

Cellulose and starch are practically deprived of reducing properties, as they 

have only one hemiacetal hydroxyl group per several hundreds or even thousands of 

glucose residues. 

 

Task №11. What are the products of partial and complete hydrolysis of starch? 

 

Example of solution: At rapid heating starch breaks into simpler molecules which 

are called dextrins with the same molecular formula as that of the starch, but with a 

smaller number of units. Further refluxing with mineral acids gives subsequent 

cleavage with formation of maltose initially and then glucose. Thus, a simplified 

starch hydrolysis can be represented as follows: 



 19 

(С6Н10О5)n(C6Н10О5)х(С12Н22О11)С6Н12О6 

starch dextrin maltose glucose 

 

Task №12. Give the structures of the vegetable and animal starch. 

 

Example of solution: Analysis of the structure of starch showed that it is not a 

unified substance, but it is a mixture of the two fractions - amylose and amylopectin. 

In most plants starch is comprised of 15-20% of amylose and 80-85% of 

amylopectin. Amylose molecule is constructed from -D-glucose units linked by 1,4-

glycosidic bonds. 

Amylose molecule contains from 200 to 1000 glucose units and has a spatial 

structure, forming a spiral coil which consists of six glucose residues. This spatial 

structure is a consequence of the axial location of hemiacetal hydroxyl group in 

glucose. Inside spiral amylose molecule there is a channel with a diameter of about 5 

nm. This channel can include molecules of suitable size, forming a special kind of 

complexes, the so-called inclusion compounds. Complex of amylose with iodine can 

serve as example of such compounds. It is blue in color, and its formation is used for 

the qualitative determination of starch. 

Amylopectin is branched polysaccharide with a molecular weight of over one 

million (polymerization degree is 6000). Amylopectin, as well as amylose, consists of 

α-D-glucose, but its molecule has more than 30 branches due to 1,6-glycosidic 

linkages. Due to branched structure amylopectin has spherical shape. 

 



 20 

O

CH
2
OH

H

H

H

H
H

OH

OH
O

O

CH
2
OH

H

H

H
H

OH

OH
O

O

CH
2

H

H

H

H

OH

OH
O

H

O

H

O

1
1

6

4

 

amylopectin 

 

Animal starch - glycogen is contained in all animal organisms. Its molecules 

are very similar to those of amylopectin, but glycogen molecules are much more 

branched. Glycogen is well soluble even in cold water. Glycogen serves as storage 

carbohydrate in the organism.  Its content in liver is about 20% and about 4% in 

muscles. All the processes of life, primarily the work of the muscles, are 

accompanied by the breakdown of glycogen, this process leads to release of energy. 

 

Task №13. Give the composition and structure of cellulose. 

 

Example of solution: Cellulose is the most abundant naturally occurring 

polysaccharide. It forms walls of the plant cells, gives the mechanical strength and 

elasticity to the plant tissues. The average molecular weight of the cellulose of plant 

origin is in the range of 100,000 to 1,000,000. Cellulose consists of residues of  

-D-glucose linked by 1,4-glycosidic bonds and has a linear structure: 

 



 21 

O

CH
2
OH

HH

H

H

OH

OH

O

CH
2
OH

H

H

H
H

OH

OH
O

O

CH
2
OH

H

H

H

OH

OH
H

H
O

H

O

H

HO

4 41 1

 

cellulose 

 

Task №14. What are heteropolysaccharides? What are their constituent parts?  

 

Example of solution: Heteropolysaccharides are polysaccharides built from the 

residues of different monosaccharides. They are widely distributed in nature in the 

form of complexes with proteins. Hyaluronic acid is contained in connective tissue, 

vitreous body of the eye, synovial fluid. On hydrolysis it produces glucosamine, 

glucuronic acid and acetic acid. The structural components of hyaluronic acid are 

glucuronic acid and N-acetylglucosamine linked by 1,3-glycosidic bonds: 

 

O

COOH

H

H

H
H

OH

OH

O

CH
2
OH

H

H
H

HNCOCH
3

OHH

O

H

O

H
 

O 1

3

 

-D-glucuronic acid N-acetyl-D-glucosamine 

1,3-glycosidic linkage 

 

Heteropolysaccharide - heparin is in the organs and tissues of animals and 

humans. Especially there are a lot of heparine in the liver, lungs, heart, and skeletal 



 22 

muscles. It was isolated in a crystalline state, and is widely used as substance for 

preventing blood coagulation (anticoagulant). Heparin molecule includes glucuronic 

acid, L-iduronic acid and partially sulfated glucosamine: 

 

O

COOH

H

H

H
H

OH

OH

O

CH
2
OSO

3
H

H

H

HNSO
3
H

H

H

OH
O

H H

O

CH
2
OSO

3
H

H

H

HNCOCH
3H

OH

H

O

COOH

H

H

H

H

OSO
3
H

OH

H

1 4

1

4 1 4
OO

O

 

heparin 

 



 23 

Revision exercises 

№ 1 

1. Write the formula of -D-glucopyranose (Haworth formula). Specify atom which 

determines its belonging to the D-series. 

2. What are the monosaccharide units in cellulose? Write a fragment of cellulose 

structure and specify the linkage between the monosaccharides. 

3. Write the reduction reaction of alkaline copper(II) hydroxide solution with glucose. 

What is the use of this reaction? 

 

№ 2 

1. Write the formula of -D-glucopyranose and its 6-phosphate (Haworth formulas). 

Specify atom which determines its belonging to the D-series.  

2. Write the hydrolysis of sucrose. Name the product. Specify the glycosidic bond in 

sucrose molecule. 

3. What property of glucose is the basis of its interaction with Fehling's reagent? 

Specify the composition of the reagent. 

 

№ 3 

1. Write the formula of -D-galactopyranose (Haworth formula). Specify atom which 

determines its belonging to the D-series. 

2. What are mucopolysaccharides? Write the structure of the components of 

chondroitin-6-sulfate and specify the nature of the linkage between them. 

3. Write the reaction of glucaric acid formation from D-glucose. Specify the 

conditions. 

 

№ 4 

1. Write the formula of -D-galactopyranose (Haworth formula). Specify atom which 

determines its belonging to the D-series. 



 24 

2. Show the structure of chondroitin-4-sulfate. Name monomers. 

3. Which properties of glucose are shown in "silver mirror" test? 

№ 5 

1. Write open-chain formulae of D-mannose and D-xylose. Specify atom which 

determines its belonging to the D-series. 

2. Write the reaction equation of glycoside formation from disaccharide maltose and 

ethanol. 

3. Which reaction can prove the existence of several hydroxyl groups in hexose? 

 

№ 6 

1. Show phenomenon of ring-chain tautomerism on example of D-ribose (furanose 

cycle). Which biopolymers contain D-ribose? 

2. Name fractions of vegetable starch. How do they differ in structure? 

3. Which polysaccharides are called homopolysaccharides? Name the 

monosaccharide units of dextran and specify the nature of bonds between them. Give 

structure of the fragment of the main chain. 

 

№ 7 

1. Write the formula of -D-ribofuranose (Haworth formula). Specify atom which 

determines its belonging to the D-series. 

2. Write formula of disaccharide consisting of D-glucuronic acid and N-

acetylglucosamine linked by 1,3-glycosidic bond. Which biopolymer is composed of 

such disaccharides? 

3. Write the reaction of D-glucuronic acid decarboxylation. Name the product 

obtained. 

 



 25 

№ 8 

1. Write the formula of -D-deoxyribofuranose (Haworth formula). Specify atom 

which determines its belonging to the D-series. 

2. Give the structure of amylopectin. Which products are obtained by its hydrolysis? 

3. Write the reaction of oxidation of D-galactose into D-galactonic acid. Specify the 

conditions. 

№ 9 

1. Write the formula of -D-deoxyribofuranose (Haworth formula). Specify atom 

which determines its belonging to the D-series.  

2. Give the structure of sucrose and explain the reason for the absence of reducing 

properties. 

3. Give an equation for the formation of D-gluconic acid from D-glucose. What is the 

oxidizing agent? 

 

№ 10 

1. Write open-chain formulae of D-ribulose and D-xylulose. Specify atom which 

determines its belonging to the D-series. 

2. What are the monosaccharide units of glycogen? Write the structure of the 

glycogen molecule and show the chain branching.  

3. What property of glucose is shown in Trommer reaction? 

 

№ 11 

1. Write the formula of -D-fructofuranose (Haworth formula). Specify atom which 

determines its belonging to the D-series.  

2. Write the hydrolysis of lactose (milk sugar). Name the products and bond in the 

molecule of lactose. 

3. Write the reaction of glucose reduction with ammoniacal silver oxide solution. 

What is the use of this reaction? 



 26 

№ 12 

1. Write the formula of -D-fructofuranose (Haworth formula). Specify atom which 

determines its belonging to the D-series.  

2. Write the hydrolysis of sucrose. Name the resulting monosaccharides. Does 

sucrose possess reducing properties? 

3. Write reaction equation of glucose with Fehling’s reagent. 

 

№ 13 

1. Write the formula of 1,6-diphosphate--D-fructofuranose in the open-chain form 

and in Haworth formula. Specify atom which determines its belonging to the D-

series. 

2. Write the hydrolysis of maltose (malt sugar). Name the products and bond in the 

molecule of maltose. 

3. How to obtain pentoses from hexuronic acids? 

 

№ 14 

1. Write 2--D and 2--D-glucosamine in pyranose ring as Haworth formulas. 

Specify atom which determines its belonging to the D-series.  

2. Write the hydrolysis of cellobiose. Name the products and bond in this molecule. 

3. What reaction can show reducing properties of glucose? 

 

№ 15 

1. Write 2--D and 2--D-galactosamine in pyranose ring as Haworth formulas. 

Specify atom which determines its belonging to the D-series.  

2. Write formula of disaccharide consisting of D-glucuronic acid and N-

acetylglucosamine linked by 1,3-glycosidic bond. Which biopolymer is composed of 

such disaccharides? 

3. What reaction can prove the presence of some hydroxyl groups in glucose? 



 27 

SUGGESTED READINGS 

1. Biologically important classes of bioorganic compounds. Biopolymers and 

their structural components: Theoretical course of biological and bioorganic 

chemistry, Module 1 / A.O. Syrovaya, E.R. Grabovetskaya, N.M. Tkachuk et al. – 

Kharkov: KhNMU. – 2013.– 183 p. 

2. Zurabyan S.E. Fundamentals of bioorganic chemistry / S.E. Zurabyan – M.: 

Geotar-Med. – 2003. – 320 p. 

3. Biological and Bioorganic Chemistry: in two books: Textbook. Textbook 1. 

Bioorganic Chemistry / B.S.Zimenkovsky, V.А.Muzychenko, I.V.Nizhenkovska, 

G.О.Syrova; edited by B.S.Zimenkovsky,  I.V.Nizhenkovska. —К. :AUP «Medicina», 

2017. — 288 p. 



 28 

Навчальне видання 

 

Вуглеводи: моносахариди. Структура і функції ди- та полісахаридів 

 

Методичні вказівки для самостійної роботи студентів 1-го курсу з 

біологічної та біоорганічної хімії 

 

 

 

Упорядники: 

Сирова Ганна Олегівна,  

Петюніна Валентина Миколаївна, 

Макаров Володимир Олександрович, 

Андрєєва Світлана Вікторівна, 

Лук’янова Лариса Володимирівна,  

Козуб Світлана Миколаївна, 

Тішакова Тетяна Станіславівна, 

Левашова Ольга Леонідівна, 

Савельєва Олена Валеріївна, 

Чаленко Наталія Миколаївна, 

Каліненко Ольга Сергіївна, 

Завада Оксана Олександрівна, 

Копотєва Наталія Василівна, 

Водолаженко Марія Олександрівна, 

Чистякова Галина Олексіївна. 

 

 

Відповідальний за випуск: Водолаженко М.О. 

Комп’ютерний набір та верстка: Водолаженко М.О.