CHEMISTRY-VIII NOTES PREPARED BY Dr.

DHONDIBA VISHWANATH SURYAWANSHI, GFGC KR PURAM BENGALURU-36

Carbohydrates 4 hours Max. Marks: 10

Derivatives of monosaccharides: Amino sugars, Haworth Structure and biological
importance of β-D-glucosamine, β-D-galactosamine and their N-acetylated forms:
N-acetyl muramic acid (NAMA);N-acetylneuraminic acid (NANA).
Sugar acids- Open or ring structure and biological importance of D-gluconic acid,
D-glucuronic acid and D-glucaric acid. Sugar phosphates - Haworth structure and
biological importance of Glucose-6-P, Fructose-6-P, Fructose-1,6-di-P, β-D-
ribose-5-P and β-D-deoxyribose-5-P.
Structure (Haworth) and biological importance of oligosaccharides- Isomaltose,
cellobiose, trehalose.
Polysaccharides- source, comparative account of partial structure and biological
function of starch,glycogen, cellulose, chitin and inulin.

Introduction: Carbohydrates are the most abundant class of biological molecules.

They are widely distributed in plants, animals and microorganisms. Carbohydrates
include simple sugars, glycogens, starches, celluloses and complex carbohydrates
such as mucopolysaccharides, glycolipids and glycoproteins. Green plants
synthesizes carbohydrates from water and carbon dioxide using solar energy.

Carbohydrates perform a wide variety of functions. They are the main source of
energy in cells. Energy is generated by the biological oxidation of simple sugars
like glucose (4kcal/g). Large polysaccharides like cellulose and chitin serve as
structural materials. Starch in plants and glycogen in animals serve as storage
forms of energy. Oligosaccharides are associated with proteins and lipids which
possess structural and regulatory role. Sugar phosphates are components of nucleic
acids and coenzymes.

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CHEMISTRY-VIII NOTES PREPARED BY Dr. DHONDIBA VISHWANATH SURYAWANSHI, GFGC KR PURAM BENGALURU-36

Classification of carbohydrates:

1) Monosaccharides: Those carbohydrates which are in simplest form, they do

not undergo hydrolysis and they are building block of carbohydrates are
called monosaccharides. Monosaccharides are water soluble and sweet in
test so it is also called simple sugars.
Examples: Glucose, fructose, galactose, etc.
Derivatives of monosaccharides: Those compounds in which carbonyl
group or alcoholic group of monosaccharides are replaced by the other
groups called derivatives of monosacchrides.
For example: amino sugar, sugar acids, sugar phosphate.
a) Amino sugar derivatives: Those derivative of sugars in which a
hydroxyl group (especially at C-2) is replaced by amino group is called
amino sugars. The amino group of amino sugar is further undergoes
acetylation to form acetylamino sugar.
Examples: β-D-Glucosamine, N-Acetyl β-D-Glucosamine, α-D-
Galactosamine, N-Acetyl α-D-Galactosamine.

Haworth Structure of β-D-Glucosamine:

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CHEMISTRY-VIII NOTES PREPARED BY Dr. DHONDIBA VISHWANATH SURYAWANSHI, GFGC KR PURAM BENGALURU-36

CH2OH
H O OH
H
OH H
HO H
H NH2
Haworth structure of D - Glucosamine

Biological importance of β-D-Glucosamine:

1) It is present in Heparin which acts as blood anticoagulant

Haworth Structure of N-Acetyl β-D-Glucosamine:

CH2OH
H O OH
H
OH H
HO H
H NHCOCH 3
Haworth structure of N - Acetyl D - Glucosamine

Biological importance of N – Acetyl β-D-Glucosamine:

1) It is present in bacterial cell wall in the form of chitin and Hyaluronic acid.
2) Chitin is a major component of shells of lobsters, crabs (crustaceae) and
scales of insects.
3) Hyaluronic acid is present in vitreous humour of eye, synovial fluid of
joints.
4) It is readily prepared by the acid hydrolysis of chitin and hence it is often
called chitosamine
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CHEMISTRY-VIII NOTES PREPARED BY Dr. DHONDIBA VISHWANATH SURYAWANSHI, GFGC KR PURAM BENGALURU-36

Haworth Structure of β-D-Galactosamine:

CH2OH
OH O OH
H
OH H
H H
H NH2
Haworth structure of D - Galactosamine

Biological importance of β-D-Galactosamine:

1) It is readily undergo acetylation to form N-acetyl β-D-Galactosamine

2) It is a component of chondro proteins found in cartilage, adult bone, cornea,
skin, tendons and heart values
3) Galactosamine is readily undergoes hydrolysis to form chondrosamine.

Haworth Structure of N –Acetyl -β-D-Galactosamine:

CH2OH
OH O OH
H
OH H
H H
H NHCOCH3
Haworth structure of N - Acetyl D - Galactosamine

Biological importance of N –Acetyl β-D-Galactosamine:

1) It is a component of chondro proteins found in cartilage, adult bone, cornea,

skin, tendons and heart values

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CHEMISTRY-VIII NOTES PREPARED BY Dr. DHONDIBA VISHWANATH SURYAWANSHI, GFGC KR PURAM BENGALURU-36

2) Galactosamine is readily undergoes hydrolysis to form chondrosamine.

Haworth structure of N –Acetyl muramic acid (NAMA):

CH2OH
H O OH
H
COOH
H C CH3 H H
HO
O

H NHCOCH3
Haworth structure of N - Acetyl muramic acid

Biological importance of N –Acetyl Muramic acid (NAMA): It is act as biopolymer

in the bacterial cell wallHaworth structure of N –Acetyl Neuraminic acid
(NANA):

H
O
O
H3C C NH COOH
H OH
H OH
CH2OH H OH
H H

OH H
Haworth structure of N - Acetyl Neuraminic acid
(NANA)

Biological importance of N –Acetyl Neuraminic acid (NANA): it is the

predominant sialic acid found in mammalian cells.

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CHEMISTRY-VIII NOTES PREPARED BY Dr. DHONDIBA VISHWANATH SURYAWANSHI, GFGC KR PURAM BENGALURU-36

b) Sugar acid derivatives: Those derivative of sugars in which a carbonyl

(aldehydic) group or primary alcoholic group or both groups undergo
oxidation to form acids called sugar acids or acid derivatives of
monosaccharides. They are three types of sugar acids.
1) D –Gluconic acid (Aldonic acid): Those derivative of D –(glucose)
sugars in which a aldehydic group is undergo oxidation using
bromine water at pH 5 to form acids called D- Gluconic acid ( aldonic
acid).
COOH
CHO
O H OH
H OH Hydrolysis HO H
Br2/H2O H OH
HO H
HO H H OH
H OH pH -5
H OH H OH
H OH
H O CH 2OH
CH 2OH
CH 2OH
D -Glucose D - Gluconic acid
D- Gluconolactone

Open chain structure of D- Gluconic (aldonic acid):

COOH
H C OH
HO C H
H C OH
H C OH
CH 2OH

Open chain structure of D - Gluconic acid

Biological importance of D- Gluconic (aldonic acid):

i) It is readily form salt with calcium which is soluble in water.

ii) It maintain the calcium level in the blood of the organism

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CHEMISTRY-VIII NOTES PREPARED BY Dr. DHONDIBA VISHWANATH SURYAWANSHI, GFGC KR PURAM BENGALURU-36

2) D -Glucuronic acid (Alduronic acid): Those derivative of D –

glucose (sugars) in which a primary alcoholic (CH2OH) group is
undergo oxidation using enzyme catalyst to form acid called D –
glucose ( alduronic acid).

CHO CHO

H OH H C OH
Enzyme
HO H
HO C H
H OH H C OH
H OH H C OH
CH 2OH
COOH
D -Glucose D -Glucuronic acid (Alduronic acid)

Open chain and Haworth structure of D -Glucuronic acid (alduronic acid):

CHO COOH
H C OH O H
H
HO C H H
OH H
H C OH
HO OH
H C OH
H OH
COOH

Open chain structure of D - Glucuronic acid Haworth structure of D - Glucuronic acid

Biological importance of D -Glucuronic acid (alduronic acid):

i) It is essential component of structural polysaccharides such as hyaluronic

acid (connective tissue) and chondroitin(cartilage)
ii) It is also a component of heparin, a polysaccharide present in blood vessels
which prevents coagulation of blood.
iii) It helps in detoxification of drugs in the system
iv) It is a component of pectin.
3) D –Glucaric acid (Aldaric acid): Those derivative of D –glucose
(sugars) in which both primary alcoholic (CH2OH) group and

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CHEMISTRY-VIII NOTES PREPARED BY Dr. DHONDIBA VISHWANATH SURYAWANSHI, GFGC KR PURAM BENGALURU-36

aldehydic group are undergo oxidation using conc. HNO 3 to form

dicarboxylic acid called D –Glucaric acid (aldaric acid).

CHO COOH

H OH H C OH
Conc. HNO 3
HO H
HO C H
H OH H C OH
H OH H C OH
CH 2OH
COOH
D -Glucose Aldaric acid (D -Glucaric acid)

Open chain structure of D –Glucaric acid (aldaric acid):

COOH
H C OH
HO C H
H C OH
H C OH
COOH
Open chain structure of Aldaric acid (D -Glucaric acid)

Biological importance of aldaric acid: It is used as identification of sugars

C) Sugar phosphate: Those derivative of sugars in which a hydroxyl (-

OH) group at position C-1 or C-6 is replaced by phosphate (PO4) group
to form phosphate ester is called sugar phosphates or phosphate
derivatives of monosaccharides.

Examples: Glucose-6-P, Fructose-6-P, Fructose-1, 6-di-P, β-D-ribose-5-P and β-

D-deoxyribose-5-P.
Haworth structure of glucose -6-phosphate:

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CHEMISTRY-VIII NOTES PREPARED BY Dr. DHONDIBA VISHWANATH SURYAWANSHI, GFGC KR PURAM BENGALURU-36

O
-
H 2C O P O
-
O
H O H
H
OH H
HO OH

H OH
 -D - Glucose - 6 - Phosphate

Haworth structure of Fructose - 6-phosphate:

-
O
- HO
O P O CH2 O

O OH H
H CH 2OH
H OH
D - Fructose - 6 - Phosphate

Haworth structure of Fructose -1, 6-diphosphate:

-
O
- HO
O P O CH2 O
-
O OH H o
H H2C O P O
-
H OH O
D - Fructose - 1, 6 - Diphosphate

Haworth structure of β-D-Ribose-5-Phosphate:

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CHEMISTRY-VIII NOTES PREPARED BY Dr. DHONDIBA VISHWANATH SURYAWANSHI, GFGC KR PURAM BENGALURU-36
-
O
- HO
O P O CH2 O

O OH H
H H
H OH
D -Ribose - 5 -Phosphate

Haworth structure of β-D-2-Deoxyribose-5-Phosphate:

-
O
- HO
O P O CH2 O

O OH H
H H
H H
D -2 -Deoxyribose - 5 -Phosphate

Biological importance of sugar phosphate:

1) These are important intermediates in the metabolism of carbohydrates

2) These are stable at neutral pH and negative charge
3) These are prevents their diffusion out of the cell
4) These are activates sugars for subsequent chemical transformation
5) Ribose – 5 phosphate and 2 –deoxyribose – 5-phosphate are the components
of nucleic acids and some coenzymes.

Oligosccharides: Those Oligosaccharides are the carbohydrates which yield a

definite number (2-9) of monosaccharide on hydrolysis (by cleavage of either
linkage which links two or more monosaccharides).

Examples: -

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CHEMISTRY-VIII NOTES PREPARED BY Dr. DHONDIBA VISHWANATH SURYAWANSHI, GFGC KR PURAM BENGALURU-36

1) Isomaltose: It is also called 6-O-α-D Glucopyranosyl –D-glucopyranose.

It is a product of partial hydrolysis of amylopectin of starch and
glycosen. It is a reducing sugar and gives two molecules of glucose on
hydrolysis.
In isomaltose, the glycosidic bond is formed between C-1 of one glucose
unit and C-6 of the second glucose unit (α -1, 6)

Haworth structure of isomaltose:

CH 2OH

H O H
H
OH H
HO
H OH O

CH2

H O H
H
OH H
HO OH
H OH

Haworth structure of Isomaltose

Biological importance of isomaltose: It is found in amylopectin and

glycogen it provides the energy for organism

2) Cellobiose: It is also called 4-O-β-D Glucopyranosyl –D-glucopyranose.

It is a product of partial hydrolysis of cellulose. It is made up of two
glucose unitsjoined through β-1,4 glycosidic linkage

Haworth structure of Cellobiose:

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CHEMISTRY-VIII NOTES PREPARED BY Dr. DHONDIBA VISHWANATH SURYAWANSHI, GFGC KR PURAM BENGALURU-36
CH 2OH
CH 2OH
H O
H H O OH
OH H O H
OH H
HO
H H
H OH
H OH

Haworth structure of Cellobiose

Biological importance of cellobiose: It is a reducing sugar formed

during the digestion of cellulose by cellulases, the enzymes present in
microorganisms.
3) Trehalose: It is also called 1-O-α-D Glucopyranosyl –1 – α -D-
glucopyranose. It is made up of two glucose units joined through α-(1,1)
glycosidic linkage. It is non – reducing sugars.
Haworth structure of trehalose:

CH 2OH H
H
H O O
H HOH 2C OH
OH H
O OH H
HO
H
H OH H
H OH
Haworth structure of Trehalose

OR

CH 2OH OH
H H
H O HO
H
H
OH H OH H
HO HOH 2C
O H
H OH O
OH
Haworth structure of Trehalose

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CHEMISTRY-VIII NOTES PREPARED BY Dr. DHONDIBA VISHWANATH SURYAWANSHI, GFGC KR PURAM BENGALURU-36

Biological importance of trehalose: It is non reducing sugar which involved in

the circulating fluid (hemolymph) of insects in which it serves as a storage form of
energy.

Polysaccharides: These are the carbohydrates of high molecular weight which

yield many (more than 9) monosaccharide molecules on hydrolysis.
Examples:
1) Starch: The most important storage of polysaccharide in plant cell is starch.
It contains two components amylose(25%) and amylopectin(75%)
i) Amylose: It consists of linear chains of D-glucose units joined
through α-1,4 glycosidic linkages. Its molecular mass can vary from
few thousand about 150000. It is soluble in water, it gives blue colour
with iodine. The iodine atoms occupy a position in the interior of a
helical coil of glucose units that is formed when amylose is suspended
in water.
Haworth structure of amylose:

CH 2OH
H CH 2OH
H O
H H O H
OH H H
OH H
O
O
H OH O
H OH
 linkage

Haworth structure of amylose

n

ii) Amylopectin: It is branched polysaccharides. In this molecule short

chains of glucose units linked through α, (1,4) linkages are joined to
each other through α (1,6) linkages. The molecular mass of
amylopectin is high upto (1 million), branching occurs every 24 -30
residues. It gives red colour with iodine.

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CHEMISTRY-VIII NOTES PREPARED BY Dr. DHONDIBA VISHWANATH SURYAWANSHI, GFGC KR PURAM BENGALURU-36

Haworth structure of amylopectin:

CH 2OH
H CH 2OH
H O
H H O H
OH H H
OH H
O

H OH O (1,6) linkage
H OH
 linkage
O

CH2
H CH 2OH
H O
H H O H
OH H H
OH H
O
O
H OH O
H OH
 linkage

Haworth structure of amylopectin n

2) Glycogen: It is a branched chain polymer similar to amylopectin. It contains

of glucose chains joined through α, (1, 4) linkages are joined to each other
through α (1,6) linkages. The branching is more extensive than in
amylopectin. Branching occurs every 8 -10 glucose residue.

Haworth structure of glycogen:

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CHEMISTRY-VIII NOTES PREPARED BY Dr. DHONDIBA VISHWANATH SURYAWANSHI, GFGC KR PURAM BENGALURU-36

CH 2 OH
H CH 2 OH
H O
H H O H
OH H H
OH H
O

H OH O (1,6) linkage
H OH
linkage
O

CH2
H CH 2 OH
H O
H H O H
OH H H
OH H
O
O
H OH O
H OH
linkage
Haworth structure of glycogen
n

Biological importance of glycogen:

1) It is the main storage polysaccharide of animal cells.
2) It abundant in the liver and also in skeletal muscle.
3) It is reserve source of energy for animals.
4) It undergoes hydrolysis enzymatically to yield glucose which is readily
oxidized to provide energy.
3) Cellulose: It is a linear polymer consisting of 10000 -15000 D – glucose
units. In this respect it resembles amylose. In cellulose, the glucose residues
are linked by β (1,4) glycosidic bonds. It is highly resistant to hydrolysis by
acids. Hydrolysis by strong acids results in glucose as the final product.
Haworth structure of cellulose:

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CHEMISTRY-VIII NOTES PREPARED BY Dr. DHONDIBA VISHWANATH SURYAWANSHI, GFGC KR PURAM BENGALURU-36

CH 2OH
CH 2OH
H O
H H O
O H
OH H O
OH H
O
H
H OH H
H OH
 linkage
n

Haworth structure of cellulose

Biological importance of cellulose:

1) It is found in the cell wall of plants
2) It is the most abundant organic compound in nature.
3) Flax and cotton contain up to 99% cellulose while wood contains 41-53%
cellulose
4) Cellulose is also not acted upon by amylases present in the digestive tract
of humans and most other higher animals. The only vertebrates able to
use cellulose as food are cattle and other ruminant animals. The extra
stomachs of the these animals contain bacteria which secrete cellulase (α,
β-glucosidase) that catalyses the hydrolysis of cellulose to form glucose.
5) Snails, termites and wood – rot fungi are some other species which
secrete cellulose and metabolise cellulose.
4) Chitin: It is linear homopolysaccharide composed of N-acetylglucosamine
residues in β (1,4) linkage. The only chemical difference from cellulose is
the replacement of the hydroxyl group at C-2 with an acetylated amino acid.
Haworth structure of chitin:

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CHEMISTRY-VIII NOTES PREPARED BY Dr. DHONDIBA VISHWANATH SURYAWANSHI, GFGC KR PURAM BENGALURU-36

CH 2OH
CH 2OH
H O
H H O
O H
OH H O
OH H
O
H
H H
NHCOCH 3 H
NHCOCH 3
 linkage n

Haworth structure of chitin

Biological importance of chitin: It is principal component of the hard

exoskeletons of nearly a million species of anthropods insects, lobsters and crabs.
5) Inulin: It is linear homopolysaccharide composed of 2 fructose residues in
β (2, 1) linkage. It is a non-reducing sugar.
Haworth structure of Inulin:
.

HO CH2 O

H OH
H CH2
OH H

HO CH2 O O

H OH
H CH2
OH H

HO CH2 O O

H OH
H H2C
OH H

n
.
Haworth structure of inulin

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CHEMISTRY-VIII NOTES PREPARED BY Dr. DHONDIBA VISHWANATH SURYAWANSHI, GFGC KR PURAM BENGALURU-36

Biological importance of inulin: It occurs in dahlia, dandelions, garlic,

onion, etc. as a storage polysaccharide. It is a polymer of 30 - 40 fructose
units i.e. fructosan with β (2, 1) linkage.

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