Carbohydrates

BIN ter
2
CARBOHYDRATES
Carbohydrates are the most abundant biomolecules on earth. Oxidation of
carbohydrates is the central energy-yielding pathway in most non-photosynthetic
cells.
Definition:Carbohydrates are polyhydroxy aldehydes or ketones, or substances that
yield such compounds on hydrolysis.
carbohydrates have the empirical formula (CH2O)n.
There are three major classes of carbohydrates:
1. Monosaccharides
Monosaccharides, or simple sugars, consist of a single polyhydroxy aldehyde or
ketone unit. The most abundant monosaccharide in nature is the six-carbon sugar D-
glucose, sometimes referred to as dextrose.
2. Oligosaccharides
Oligosaccharides consist of short chains of monosaccharide units, or residues,
joined by characteristic linkages called glycosidic bonds. The most abundant are the
disaccharides, with two monosaccharide units. Example: sucrose (cane sugar).
3. Polysaccharides
The polysaccharides are sugar polymers containing more than 20 or so
monosaccharide units, and some have hundreds or thousands of units. Example:
starch.
Polysaccharides are of two types based on their function and composition. Based on
function, polysaccharides of two types storage and structural.
A. Storage polysaccharide - starch.
B. Structural polysaccharide - cellulose.
21FT3251- Biochemistry Department ofFood Technology IIISemester
- UNIT 1

SBT1102 - Biochemistry BTE/BME/BIN II Semester
3
General properties of carbohydrates
• Carbohydrates act as energy reserves, also stores fuels, and metabolic
intermediates.
• Ribose and deoxyribose sugars forms the structural frame of the genetic
material, RNA and DNA.
• Polysaccharides like cellulose are the structural elements in the cell walls of
bacteria and plants.
• Carbohydrates are linked to proteins and lipids that play important roles in cell
interactions.
• Carbohydrates are organic compounds, they are aldehydes or ketones with
many hydroxyl groups.
Physical Properties of Carbohydrates
• Steroisomerism - Compound shaving same structural formula but they differ in
spatial configuration. Example: Glucose has two isomers with respect to
penultimate carbon atom. They are D-glucose and L-glucose.
• Optical Activity - It is the rotation of plane polarized light forming (+)
glucose and (-) glucose.
• Diastereoisomeers - It the configurational changes with regard to C2, C3, or
C4 in glucose. Example: Mannose, galactose.

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• Annomerism - It is the spatial configuration with respect to the first carbon
atom in aldoses and second carbon atom in ketoses.
Biological Importance
• Carbohydrates are chief energy source, in many animals, they are instant
source of energy. Glucose is broken down by glycolysis/ kreb's cycle to yield
ATP.
• Glucose is the source of storage of energy. It is stored as glycogen in animals
and starch in plants.
• Stored carbohydrates acts as energy source instead of proteins.
• Carbohydrates are intermediates in biosynthesis of fats and proteins.
• Carbohydrates aid in regulation of nerve tissue and is the energy source for
brain.
• Carbohydrates gets associated with lipids and proteins to form surface
antigens, receptor molecules, vitamins and antibiotics.
• They form structural and protective components, like in cell wall of plants and
microorganisms.
• In animals they are important constituent of connective tissues.
• They participate in biological transport, cell-cell communication and activation
of growth factors.
• Carbohydrates that are rich in fibre content help to prevent constipation.
• Also they help in modulation of immune system.
Monosaccharides
• The word “Monosaccharides” derived from the Greek word “Mono” means
Single and “saccharide” means sugar
• Monosaccharides are polyhydroxy aldehydes or ketones which cannot be
further hydrolysed to simple sugar.
• Monosaccharides are simple sugars. They are sweet in taste. They are
soluble in water. They are crystalline in nature.
• They contain 3 to 10 carbon atoms, 2 or more hydroxyl (OH) groups and one
aldehyde (CHO) or one ketone (CO) group.
Classification of Monosaccharides

5
Monosaccharides are classified in two ways. (a) First of all, based on the
number of carbon atoms present in them and (b) secondly based on the presence of
carbonyl group.
The naturally occurring monosaccharides contain three to seven carbon
atoms per molecule. Monosaccharides of specific sizes may be indicated by names
composed of a stem denoting the number of carbon atoms and the suffix -ose. For
example, the terms triose, tetrose, pentose, andhexose signify monosaccharides
with, respectively, three, four, five, and six carbon atoms. Monosaccharides are also
classified as aldoses or ketoses. Those monosaccharides that contain an aldehyde
functional group are called aldoses; those containing a ketone functional group on
the second carbon atom are ketoses. Combining these classification systems gives
general names that indicate both the type of carbonyl group and the number of
carbon atoms in a molecule. Thus, monosaccharides are described as aldotetroses,
aldopentoses, ketopentoses, ketoheptoses, and so forth. Glucose and fructose are
specific examples of an aldohexose and a ketohexose, respectively.

6
Trioses
Trioses are “Monosaccharides” containing 3 carbon atoms. The molecular formula of
triose is C3H6O3
Characteristics
• Trioses are simple sugars
• They are soluble in water
• They are sweet in taste.
• The triose may contain an aldehyde group (aldotriose) or a ketone group
(ketotriose). Example Glycerose and Dehydroxyacetone
Tetroses
Tetroses are “Monosaccharides” containing 4 carbon atoms. The molecular formula
of tetrose is C4H8O4
Characteristics

SBT1102 - Biochemistry
• Tetroses are simple sugars
• Tetroses are soluble in water
• They are crystalline forms.
• The tetroses may contain an aldehyde group (
(ketotetrose).
Pentoses
Pentoses are “Monosaccharides” containing 5 carbon atoms. It is an important
component of “nucleic acid”. The molecular formula of Pentose is C5H10O5
Characteristics
• Pentoses are simple sugars
• Pentoses are soluble in water
• The pentoses may contain an aldehyde group (aldopentose) or a ketone
group (ketopentose).
Erythrose
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Tetroses are simple sugars
Tetroses are soluble in water
They are sweet in taste.
forms.
The tetroses may contain an aldehyde group (aldotetrose) or a ketone group
are simple sugars
Pentoses are soluble in water
forms.
The pentoses may contain an aldehyde group (aldopentose) or a ketone
II Semester
aldotetrose) or a ketone group
The pentoses may contain an aldehyde group (aldopentose) or a ketone

Hexoses
Hexoses are “Monosaccharides
of Hexose is C6H12O6
Characteristics
• Hexoses are simple sugars
• Hexoses are soluble in water
• The pentoses may contain an aldehyde group (aldohexose
(ketohexose).
Structure of Monosaccharides
1. Straight or Open Chain Structure
arranged in a straight line. It is also called open chain structure because the two
ends remain separate and they are not linked. Open chain structure are of two
types –
• (a)Structure proposed by Fittig and Baeyer
• (b)Structure proposed by Fischer known as Fischer’s Projection Formula
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Hexoses are “Monosaccharides” containing 6 carbon atoms. The molecular formula
Hexoses are simple sugars
Hexoses are soluble in water
forms.
The pentoses may contain an aldehyde group (aldohexose) or a ketone group
Structure of Monosaccharides
Straight or Open Chain Structure: Here 6 carbon atoms of glucose are
(a)Structure proposed by Fittig and Baeyer
ucture proposed by Fischer known as Fischer’s Projection Formula
II Semester
” containing 6 carbon atoms. The molecular formula
) or a ketone group
Here 6 carbon atoms of glucose are
ucture proposed by Fischer known as Fischer’s Projection Formula.

2. Cyclic or Ring Structure:
Haworth (1929) proposed this formula and hence the name Haworth’s Projection
Formula. The sugar molecules exist in two type of rings which are as follows
(a)Furanose Ring – 5 membered ring
(b)Pyranose Ring- 6 membered ring
Properties of Monosaccharides
1.Colour - colourless
2.Shape - crystalline
3.Solubility – water soluble
4.Taste - sweet
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or Ring Structure: Here the atoms are arranged in the form of a ring.
Formula. The sugar molecules exist in two type of rings which are as follows
5 membered ring
6 membered ring
Properties of Monosaccharides
II Semester
Here the atoms are arranged in the form of a ring.
Formula. The sugar molecules exist in two type of rings which are as follows –

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5.Optical activity – Optically active. (a) Dextrorotatory (‘d’ form) and (b) Levorotatory
(‘l’ form)
6.Mutarotation – The change in specific rotation of an optically active compound is
called mutarotation. +1120 +52.50 +190 α-D-glucose β -D-glucose
7. Glucoside formation -
Glucose + Methyl alcohol = Methyl glucoside
8. Esterification –

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9. Reducing agents –
Monosaccharides reduce oxidizing agent such as hydrogen peroxide. In such
reaction, sugar is oxidized at the carbonyl group and oxidizing agent becomes
reduced.
C6H12O6 + 2 Cu(OH)2→C6H12O7 + Cu2O + 2H2O
Glucose Fehling’s GluconicCuprous
solutionacid oxide
10. Formation of Osazone –
Disaccharides
Disaccharides consist of two sugars joined by an O-glycosidic bond.
The most abundant disaccharides are sucrose,lactose and maltose.
Other disaccharides include isomaltose, cellobiose and trehalose.
The disaccharides can be classified into:
1. Homodisaccharides

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2. Heterodisaccharides.
Hommodisaccharides Maltose
(malt sugar )
Isomaltose Celebiose
structure 2α-glucose 2 α-glucose 2β-D-glucose
Type of bond α-1-4
glucosidicbond
α1-6
glucosidicbond
β1-4
glucosidicbond.
Anomeric Carbon Free Free Free
Reducing Property Reducing Reducing Reducing
Produced by It is produced
from starch by the
action of amylase
by the hydrolysis
of some
polysaccharides
such as dextran
by the acid
hydrolysis of
cellulose
Heterodisaccharides: are formed of 2 different monosaccharide units
Heterodisaccharides Sucrose Lactose
Composition α-D-glucose+ β–D-fructose β-D-galactoseand β-D-
glucose
Type of bond α-1-β-2 glucosidic bond OR
β 2-α-1 fructosidic bond
a β (14)
galactosidicbond
AnomericC no free aldehydeor free

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ketonegroup
Reducing property is not a reducing sugar Reducing
Composition α-D-glucose+β–D-fructose β-D-galactoseandβ-D-
glucose
AnomericC nofreealdehydeorketonegroup free
Effectofhydrolysis The hydrolysis of sucrose to
glucose and fructose is
catalysed by sucrose (also
called invertase),
Hydrolysed by the
intestinal lactase
enzyme into galactose
and glucose
Present in Table sugar
Cane sugar,
beet sugar
Milk sugar
It may appear in urine in
late pregnancy and
during lactation

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Polysaccharides
Polysaccharides contain hundreds or thousands of carbohydrate units.
• Polysaccharides are not reducing sugars, since the anomeric carbons are
connected through glycosidic linkages.
• Nomenclature:
Homopolysaccharide- a polysaccharide is made up of one type of
monosaccharide unit
Heteropolysaccharide- a polysaccharide is made up of more than one type of
monosaccharide unit
Starch
• Starch is a polymer consisting of D-glucose units.
• Starches (and other glucose polymers) are usually insoluble in water because
of the high molecular weight, but they can form thick colloidal suspensions
with water.

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• Starch is a storage compound in plants, and made of glucose units
• It is a homopolysaccharide made up of two components: amylose and
amylopectin.
• Most starch is 10-30% amylose and 70-90% amylopectin.
• Amylose – a straight chain structure formed by 1,4 glycosidic bonds
between α-D-glucose molecules.
Structure of Amylose Fraction of Starch
• The amylose chain forms a helix.
• This causes the blue colour change on reaction with iodine.
• Amylose is poorly soluble in water, but forms micellar suspensions
• Amylopectin-a glucose polymer with mainly α -(1→4) linkages, but it also has
branches formed by α -(1→6) linkages. Branches are generally longer than
shown above.
Structure of Amylopectin Fraction of Starch
• Amylopectin causes a red-violet colour change on reaction with iodine.
• This change is usually masked by the much darker reaction of amylose to
iodine.
Glycogen
• Storage polysaccharide in animals
• Glycogen constitutes up to 10% of liver mass and 1-2% of muscle mass
H O
OH
H
OH
H
OH
CH2OH
H
O H
H
OH
H
OH
CH2OH
H
O
H
H H O
O
H
OH
H
OH
CH2OH
H
H H O
H
OH
H
OH
CH2OH
H
OH
H
H O
O
H
OH
H
OH
CH2OH
H
O
H
1
6
5
4
3
1
2
amylose
H O
OH
H
OH
H
OH
CH2OH
H
O H
H
OH
H
OH
CH2OH
H
O
H
H H O
O
H
OH
H
OH
CH2
H
H H O
H
OH
H
OH
CH2OH
H
OH
H
H O
O
H
OH
H
OH
CH2OH
H
O
H
O
1 4
6
H O
H
OH
H
OH
CH2OH
H
H H O
H
OH
H
OH
CH2OH
H
H
O
1
OH
3
4
5
2
amylopectin

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• Glycogen is stored energy for the organism
• Similar in structure to amylopectin, only difference from starch: number of
branches
• Alpha(1,6) branches every 8-12 residues
• Like amylopectin, glycogen gives a red-violet color with iodine
Cellulose
• The β-glucose molecules are joined by condensation, i.e. the removal of
water, forming β-(1,4) glycosidic linkages.
• The glucose units are linked into straight chains each 100-1000 units long.
• Weak hydrogen bonds form between parallel chains binding them into
cellulose microfibrils.
• Cellulose microfibrils arrange themselves into thicker bundles called
microfibrils. (These are usually referred to as fibres.)
• The cellulose fibres are often “glued” together by other compounds such as
hemicelluloses and calcium pectate to form complex structures such as plant
cell walls.
• Because of the β-linkages, cellulose has a different overall shape from
amylose, forming extended straight chains which hydrogen bond to each
other, resulting in a very rigid structure.

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• Cellulose is an important structural polysaccharide, and is the single most
abundant organic compound on earth. It is the material in plant cell walls that
provides strength and rigidity; wood is 50% cellulose.
• Most animals lack the enzymes needed to digest cellulose, although it
does provide needed roughage (dietary fiber) to stimulate contraction of the
intestines and thus help pass food along through the digestive system
• Some animals, such as cows, sheep, and horses, can process cellulose
through the use of colonies of bacteria in the digestive system which are
capable of breaking cellulose down to glucose; ruminants use a series of
stomachs to allow cellulose a longer time to digest. Some other animals such
as rabbits reprocess digested food to allow more time for the breakdown of
cellulose to occur.
• Cellulose is also important industrially, from its presence in wood, paper,
cotton, cellophane, rayon, linen, nitrocellulose (guncotton), photographic films
(cellulose acetate), etc.
CHITIN
• Chitin is a polymer that can be found in anything from the shells of beetlesto
webs of spiders. It is present all around us, in plant and animal creatures.
• It is sometimes considered to be a spinoff of cellulose, because the two are
very molecularly similar.
• Cellulose contains a hydroxy group, and chitin contains acetamide.
• Chitin is unusual because it is a "natural polymer," or a combination of
elements that exists naturally on earth.
• Usually, polymers are man-made. Crabs, beetles, worms and mushrooms
contain large amount of chitin.
• Chitin is a very firm material, and it help protect an insect against harm and
pressure

Inulin
• Inulin is stored in the tubers of the dahlia and artichoke and in the roots of
dandelion. It is also found in onion and garlic.
• Inulin (Fig. 8–4) has a molecular weight of about 5,000 and consists of about
30–35 fructose units per molecule.
• It is formed in the plants by eliminating a molecule of water from the glycosidic
OH group on carbon atom 2 of one
group on carbon atom 1 of the adjacent
Pectin
• Pectins are found as intercellular substances in the tissues of young plants
and are especially abundant in ripe fruits such as guava, apples and pears.
• Pectin is a polysaccharide of
carboxyl groups are, either partly or completely, esterified with methyl alcohol
and others are combined withcalcium or magnesium ions. Chemically, they
are called polygalacturonides
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is stored in the tubers of the dahlia and artichoke and in the roots of
dandelion. It is also found in onion and garlic.
4) has a molecular weight of about 5,000 and consists of about
ructose units per molecule.
lants by eliminating a molecule of water from the glycosidic
OH group on carbon atom 2 of one β-D-fructose unit and the alcoholic OH
group on carbon atom 1 of the adjacent β-D-fructose unit.
are found as intercellular substances in the tissues of young plants
Pectin is a polysaccharide of α-D-galacturonic acid where some of the free
groups are, either partly or completely, esterified with methyl alcohol
are called polygalacturonides
II Semester
is stored in the tubers of the dahlia and artichoke and in the roots of
4) has a molecular weight of about 5,000 and consists of about
lants by eliminating a molecule of water from the glycosidic
fructose unit and the alcoholic OH
are found as intercellular substances in the tissues of young plants
galacturonic acid where some of the free
groups are, either partly or completely, esterified with methyl alcohol

19
Mucopolysaccharides
Polysaccharides that are composed not only of a mixture of simple sugars but
also of derivatives of sugars such as amino sugars and uronic sugars are called
mucopolysaccharides.
Hyaluronic acid
• It is the most abundant member of mucopolysaccharides and is found in
higher animals as a component of various tissues such as the vitreous body
of the eye, the umbilical cord and the synovial fluid of joints.
• It is a straight-chain polymer of D-glucuronic acid and N-acetyl- D-
glucosamine (NAG) alternating in the chain. Its molecular weight approaches
approximately, 5,000,000. linkages invloved, β-1 → 3 and β-1 → 4.
Chondroitin
• Chondroitin is of limited distributioin. It is found in cartilage and is also a
component of cell coats. It is a parent substance for two more widely
distributed mucopolysaccharides, chondroitin sulfate A and chondroitin sulfate
B.
• Chondroitin is similar in structure to hyaluronic acid except that it contains
galactosamine rather than glucosamine. It is, thus, a polymer of β-
Dglucuronido- 1, 3-N-acetyl-D-galactosamine joined by β- 1 → 4 linkages.
• The two chondroitin sulfate A and C are widely distributed and form major
structural components of cartilage, tendons and bones.
• Chondroitin sulfates may be regarded as derivatives of chondroitin where, in
thegalactosamine moiety, a sulfate group is esterified either at carbon 4 as in
chondroitin sulfate A or at carbon 6 as in chondroitin sulfate C

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• The two linkages involved in both types of chondroitin sulfate would,
obviously, be the same. These are β-1 → 3 and β-1 → 4.
Dermatan Sulfate
• Dermatan sulfate is a mucopolysaccharide structurally similar to chondroitin
sulfate A except that the D-glucuronic acid is replaced by L-iduronic acid
• The two linkages involved are α-1 → 3 and β-1 → 4. Dermatan sulfate is also
known byits conventional name, chondroitin sulfate B.
Keratosulfate
• Keratosulfate differs from other mucopolysaccharides in that the uronic acid
component is replaced by D-galactose. Here, the second acetylated amino
sugar component (which is N-acetyl-D-glucosamine in this case) is esterified
by a sulfate group at carbon 6. Although, the two alternating linkages involved
are β-1 → 4 and β-1 → 3, in this case the linkage between the repeating
disaccharide units is β-1 →3 rather than β-1 → 4.
Heparin
• composed of D-glucuronic acid units, most of which (about 7 out of every 8)
are esterified at C2 and D-glucosamine-N-sulfate (= sulfonylaminoglucose)

units with an additional O
polymer are alternating
corresponds to about 5
• Heparin acts as an anticoagulant. It
the prothrombin thrombin
fibrinogen.
The following table is the list of biologically important polysaccharides and their
functions. Polysaccharides are
Name of the
Polysaccharide
Composition
Starch
Polymer of glucose
containing a straight
chain of glucose molecules
(amylose) and a branched
(amylopectin)
Glycogen Polymer of glucose
Cellulose Polymer of glucose
Insulin Polymer of fructose
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units with an additional O-sulfate group at C6. Both the linkages of the
polymer are alternating α-1 → 4. Thus, the sulfate content is very high and
corresponds to about 5–6 molecules per tetrasaccharide repeating unit.
Heparin acts as an anticoagulant. It prevents coagulation of blood by inhibiting
thrombin conversion. This eliminates the effect of thrombin on
Polysaccharides are complex carbohydrates.
Composition Occurrence Functions
Polymer of glucose
containing a straight
(amylose) and a branched
(amylopectin)
In several plant
species as main
storage
carbohydrate
storage of
reserve food
Polymer of glucose
Animals (equivalent
of starch)
Storage of
reserve food
Polymer of glucose
Different regions of
plant, in sieve tubes
of phloem
Cell wall matrix
Polymer of fructose
In roots and tubers
(like Dahlia)
Storage of
reserve food
II Semester
sulfate group at C6. Both the linkages of the
4. Thus, the sulfate content is very high and
6 molecules per tetrasaccharide repeating unit.
prevents coagulation of blood by inhibiting
conversion. This eliminates the effect of thrombin on
Functions
storage of
reserve food
Storage of
reserve food
Cell wall matrix
Storage of
reserve food

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Pectin
Polymer of galactose and
its derivatives
Plant cell wall Cell wall matrix
Hemi cellulose
Polymer of pentoses and
sugar acids
Plant cell wall Cell wall matrix
Lignin Polymer of glucose
Plant cell wall (dead
cells like
sclerenchyma)
Cell wall matrix
Chitin Polymer of glucose
Bodywall of
arthropods. In some
fungi also
Exoskeleton
Impermeable to
water
Murein
Polysaccharide cross
linked with amino acids
Cell wall of
prokaryotic cells
Structural
protection
Hyaluronic acid Polymer of sugar acids
Connective tissue
matrix, Outer coat of
mammalian eggs
Ground
substance,
protection
Chrondroitin
sulphate
Polymer of sugar acids
Connective tissue
matrix
Ground
substance
Heparin
Closely related to
chrondroitin
Connective tissue
cells
Anticoagulant
Gums and
mucilages
Polymers of sugars and
sugar acids
Gums - bark or
trees. Mucilages -
flower
Retain water in
dry seasons

Carbohydrates

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