OPTOM FASLU MUHAMMED

© SSER Ltd.
 The Nature of Carbohydrates
Carbohydrates are compounds of great importance in both the biological and
commercial world
They are used as a source of energy in all organisms and as structural materials in
membranes, cell walls and the exoskeletons of many arthropods
All carbohydrates contain the elements carbon (C), hydrogen (H) and oxygen (O)
with the hydrogen and oxygen being present in a 2 : 1 ratio
THE GENERAL FORMULA OF A CARBOHYDRATE IS:

Cx(H2O)y
EXAMPLES

The formula for glucose is C6H12O6

The formula for sucrose is C12H22O11
Carbohydrates (glycans) have the following
basic composition: I
(CH2O)n or H - C - OH
I
 Monosaccharides - simple sugars with multiple OH
groups. Based on number of carbons (3, 4, 5, 6), a
monosaccharide is a triose, tetrose, pentose or hexose.
 Disaccharides - 2 monosaccharides covalently linked.
 Oligosaccharides - a few monosaccharides covalently
linked.
 Polysaccharides - polymers consisting of chains of
monosaccharide or disaccharide units.
 THE CLASSIFICATION OF CARBOHYDRATES
Carbohydrates are classified as either sugars or polysaccharides

CARBOHYDRATES

SUGARS POLYSACCHARIDES

MONOSACCHARIDES DISACCHARIDES STORAGE STRUCTURAL

Monosaccharides are Disaccharides are GLYCOGEN and CELLULOSE
single sugar units thatdouble sugar units that STARCH are and CHITIN are
include: include: storage important
GLUCOSE SUCROSE carbohydrates; structural
FRUCTOSE MALTOSE animal cells store carbohydrates;
GALACTOSE LACTOSE glucose as cellulose forms
glycogen and the fabric of
plant cells store many cells walls
glucose as starch and chitin is a
major component
of the
exoskeletons of
GLUCOSE many arthropods
 MONOSACCHARIDES
Monosaccharides are single sugar units that form the building blocks for
the larger carbohydrates
There are many different monosaccharides; they vary according to the number
of carbon atoms that they possess and in the way the atoms are arranged
in the molecules
Glucose, the main source of energy for most organisms, is a hexose sugar with
six carbon atoms and the formula C6H12O6
Glucose exists in both straight chain and ring form with rings forming when
1 glucose is dissolved in water
H C O H
2 6
H C O H H C O H
3 5
H O C H C O
H H
4
H C O H 4
H
1
C C
5 O H H
H C O H H O O H
3 2
6 C C
H C O H
H O H
H
CHAIN STRUCTURE RING STRUCTURE
Classification of Monosaccharides

•The monosaccharides are the simplest of the carbohydrates,

since they contain only one polyhydroxy aldehyde or ketone
unit.

•Monosaccharides are classified according to the number of

carbon atoms they contain:

•Thepresence of an aldehyde is indicated by the prefix aldo-

and a ketone by the prefix keto-.

Monosaccharide
3C- triose (DHAP) glyceraldehyde
4C- tetrose erythrose
5C- pentose arabinose
6C- hexose
 GLUCOSE
This straight chain 1
representation of the glucose H C O ALDEHYDE GROUP
molecule shows how the
carbon atoms are numbered
2
Glucose, in common with H C O H
many other hexose sugars
has an aldehyde group 3 The carbon atom
as part of the structure H O C H of the carbonyl group
is referred to as the
The carbon atom that 4 ANOMERIC CARBON
forms part of this aldehyde H C O H ATOM and, for glucose,
group is always carbon 1
this is carbon 1
5
The C = O carbonyl group H C O H
has reducing properties such
that all monosaccharides 6
are reducing sugars H C O H
The remainder of the molecule
is a series of bonded carbon H
atoms with attached hydrogen
atoms and hydroxyl (OH) groups
 GLUCOSE
In solution glucose exists in ring form
Glucose forms a H
six-membered ring when
the hydroxyl group (OH) 6
on carbon 5 adds to the H C O H
aldehyde group on
5
carbon 1 C O
H H
4
H
C 1
C
O H H
H O O H
3 2
C C

H O H
 Hemiacetal & hemiketal formation

H H
An aldehyde can
C O + R' OH R' O C OH
react with an
alcohol to form R R
a hemiacetal. aldehyde alcohol hemiacetal

R R
A ketone can
react with an C O + "R OH "R O C OH
alcohol to form R' R'
a hemiketal. ketone alcohol hemiketal
 1
CHO
Pentoses and
H C OH
hexoses can cyclize 2
HO C H
as the ketone or 3 D-glucose
aldehyde reacts H C OH (linear form)
4
with a distal OH. H
5
C OH

Glucose forms an 6
CH2OH
intra-molecular 6 CH2OH 6 CH2OH
hemiacetal, as the 5 O 5 O
H H H OH
C1 aldehyde & H H
4 H 1 4 H 1
C5 OH react, to OH OH
OH OH OH H
form a 6-member 3 2 3 2

pyranose ring, H OH H OH

named after pyran. α-D-glucose β-D-glucose

These representations of the cyclic sugars are called

Haworth projections.
Fructose forms either
 a 6-member pyranose ring, by reaction of the C2 keto
group with the OH on C6, or
 a 5-member furanose ring, by reaction of the C2 keto
group with the OH on C5.
 6 CH2OH 6 CH2OH
5 O 5 O
H H H OH
H H
4 H 1 4 H 1
OH OH
OH OH OH H
3 2 3 2
H OH H OH
α-D-glucose β-D-glucose

Cyclization of glucose produces a new asymmetric center

at C1. The 2 stereoisomers are called anomers, α & β.
Haworth projections represent the cyclic sugars as having
essentially planar rings, with the OH at the anomeric C1:
 α (OH below the ring)
 β (OH above the ring).
 GLUCOSE
The ring structure of glucose is usually represented in
Howarth projection

C H 2O H
H O H
H 1
O H H
HO O H
H O H
 ISOMERS
Each hexose sugar exists in both alpha and beta forms

These ISOMERS can be distinguished by the arrangement of the

OH and H groups about the extreme right carbon atom IN the ring
 Monosaccharides
Aldoses (e.g., glucose) have Ketoses (e.g., fructose) have
an aldehyde group at one end. a keto group, usually at C2.
H O
C CH2OH

H C OH C O

HO C H HO C H

H C OH H C OH

H C OH H C OH

CH2OH CH2OH

D-glucose D-fructose
 D vs L Designation

CHO CHO
D & L designations
H C OH HO C H
are based on the
configuration about CH2OH CH2OH
the single asymmetric D-glyceraldehyde L-glyceraldehyde
C in glyceraldehyde.
CHO CHO
The lower H C OH HO C H
representations are
CH2OH CH2OH
Fischer Projections.
D-glyceraldehyde L-glyceraldehyde
 Sugar Nomenclature

For sugars with more O H O H

than one chiral center, C C
D or L refers to the H – C – OH HO – C – H
asymmetric C farthest HO – C – H H – C – OH
from the aldehyde or H – C – OH HO – C – H
keto group. H – C – OH HO – C – H
CH2OH CH2OH
Most naturally occurring
D-glucose L-glucose
sugars are D isomers.
D & L sugars are mirror O H O H
images of one another. C C
They have the same H – C – OH HO – C – H
name, e.g., D-glucose HO – C – H H – C – OH
& L-glucose. H – C – OH HO – C – H
Other stereoisomers H – C – OH HO – C – H
have unique names, CH2OH CH2OH
e.g., glucose, mannose, D-glucose L-glucose
galactose, etc.
The number of stereoisomers is 2n, where n is the
number of asymmetric centers.
The 6-C aldoses have 4 asymmetric centers. Thus there
are 16 stereoisomers (8 D-sugars and 8 L-sugars).
 Properties of glucose
• Oxidation
• Monosaccharides are easily oxidised by the
oxidising agents.
• With mild reagents such as Tollen’s reagent
Glucose gives Gluconic acid.
Pottasium ferricyanide can be reduced to
ferrocyanide .(test for sugars having free
carbonyl groups. Hence also called
reducing sugars.
• Strong oxidizing agents like Conc nitric acid
yields dicarboxylic acid Saccharic acid.
• Reduction
• Free CHO & C=O of monosacchrides are
reduced to alcohol by sodium amalgam and
water.
• Glucose yields Sorbitol & Mannitol.
• Free CHO & C=O groups of sugar reacts
with phenyl hydrazine to form
corresponding osazone.
• Glucose – Glucosazone
• Reaction with HCN – Cyanohydrin
• Esterification- The hydroxyl group of
alcohols in the carbohydrate may be
converted to esters by treatment with
acetylating agents.(Glucose Penta Acetate)
Formation of Phosphate Esters
•Phosphate esters can form at the 6-carbon of
aldohexoses and aldoketoses.

• •Phosphate esters of monosaccharides are

found in the sugar-phosphate backbone of
DNA and RNA, in ATP, and as intermediates
in the metabolism of carbohydrates in the
body.
• Methylation
• Reacting with methyl alcohol monosaccrides
yields glycosides
• Fermentation
• Mono sacchrides like glucose & fructose
yields ethanol & Carbon dioxide on
hydrolysis
• MUTAROTATION
The two stereoisomeric forms of glucose,
i.e., α-D-glucose and β-D-glucose exist in
separate crystalline forms and thus have
different melting points and specific
rotations. For example α-D-glucose has a
m.p. of 419 K with a specific rotation of
+112° while β-D-glucose has a m.p. of 424
K and has a specific rotation of +19°.
• However, when either of these two forms is
dissolved in water and allowed to stand, it
gets converted into an equilibrium mixture
of α-and β-forms through a small amount of
the open chain form.
• As a result of this equilibrium, the specific
rotation of a freshly prepared solution of α-
D-glucose gradually decreases from of
+112° to +52.7° and that of β-D-glucose
gradually increases from +19° to +52.7°.
•
• This change in specific rotation of an
optically active compound in solution with
time, to an equilibrium value, is called
mutarotation.
• During mutarotation, the ring opens and
then recloses either in the inverted position
or in the original position giving a mixture
of α-and-β-forms.
• All reducing carbohydrates, i.e.,
monosaccharides and disacchardies
(maltose, lactose etc.) undergo mutarotation
in aqueous solution.
Galactose
Ring structure
Fructose

CH2OH

C O

HO C H

H C OH

H C OH

CH2OH

D-fructose
 H OH H OH
4 6 H O H O
HO 5 HO
HO 2 H HO OH
3 H OH 1 H OH
H OH H H

α-D-glucopyranose β-D-glucopyranose

Because of the tetrahedral nature of carbon bonds,

pyranose sugars actually assume a "chair" or "boat"
configuration, depending on the sugar.
The representation above reflects the chair configuration
of the glucopyranose ring more accurately than the
Haworth projection.
 Glycosidic Bonds
The anomeric hydroxyl and a hydroxyl of another sugar
or some other compound can join together, splitting out
water to form a glycosidic bond:
R-OH + HO-R'  R-O-R' + H2O
E.g., methanol reacts with the anomeric OH on glucose
to form methyl glucoside (methyl-glucopyranose).
H OH H OH
H O H2O H O
HO HO
HO H + CH3-OH HO H
H OH H OH
H OH H OCH3
α-D-glucopyranose methanol methyl-α-D-glucopyranose
 6 CH2OH 6 CH2OH

Disaccharides: H
5 O H H
5 O H
H H
Maltose, a cleavage 4 OH H 1 4
OH H 1

product of starch OH 3 2
O
3 2
OH

(e.g., amylose), is a H OH maltose H OH

disaccharide with an
α(1→ 4) glycosidic 6 CH2OH 6 CH2OH

5 O 5 O
link between C1 - C4 H
H
H
H
OH

OH of 2 glucoses. 4
OH H 1 O 4
OH H 1

H H
It is the α anomer OH 3 2 3 2

H OH
(C1 O points down). cellobiose
H OH

Cellobiose, a product of cellulose breakdown, is the

otherwise equivalent β anomer (O on C1 points up).
The β(1→ 4) glycosidic linkage is represented as a zig-zag,
but one glucose is actually flipped over relative to the other.
Other disaccharides include:
 Sucrose, common table sugar, has a glycosidic bond
linking the anomeric hydroxyls of glucose & fructose.
Because the configuration at the anomeric C of glucose
is α (O points down from ring), the linkage is α(1→2).
The full name of sucrose is α-D-glucopyranosyl-(1→2)-
β-D-fructopyranose.)
 Lactose, milk sugar, is composed of galactose &
glucose, with β(1→4) linkage from the anomeric OH of
galactose. Its full name is β-D-galactopyranosyl-(1→ 4)-
α-D-glucopyranose
 CH2OH 6CH OH CH2OH CH2OH CH2OH
2
O 5 O O H O H O OH
H H H
H H H H H
OH H 1 O 4 OH H 1 O OH H O OH H O OH H
OH H H H
H 2 H
3
H OH H OH H OH H OH H OH
cellulose
Cellulose, a major constituent of plant cell walls, consists
of long linear chains of glucose with β(1→4) linkages.
Every other glucose is flipped over, due to β linkages.
This promotes intra-chain and inter-chain H-bonds and
van der Waals interactions,
that cause cellulose chains to
be straight & rigid, and pack
with a crystalline arrangement
in thick bundles - microfibrils.
See: Botany online website; Schematic of arrangement of
website at Georgia Tech. cellulose chains in a microfibril.
 CH2OH 6CH OH CH2OH CH2OH CH2OH
2
O 5 O O H O H O OH
H H H
H H H H H
OH H 1 O 4 OH H 1 O OH H O OH H O OH H
OH H H H
H 2 H
3
H OH H OH H OH H OH H OH
cellulose

Multisubunit Cellulose Synthase complexes in the plasma

membrane spin out from the cell surface microfibrils
consisting of 36 parallel, interacting cellulose chains.
These microfibrils are very strong.
The role of cellulose is to impart strength and rigidity to
plant cell walls, which can withstand high hydrostatic
pressure gradients. Osmotic swelling is prevented.
Explore and compare structures of amylose & cellulose
using Chime.
 DISACCHARIDES
Disaccharides are sugars composed of two monosaccharides covalently bonded
together by a glycosidic linkage

Maltose, also known as malt sugar, is formed from two glucose molecules

Lactose, or milk sugar, is a disaccharide formed when the monosaccharides

glucose and galactose bond

Sucrose is common household sugar and is formed when the monosaccharides

glucose and fructose bond

MALTOSE = GLUCOSE + GLUCOSE

LACTOSE = GLUCOSE + GALACTOSE
SUCROSE = GLUCOSE + FRUCTOSE
 THE FORMATION OF MALTOSE
Maltose forms C H 2O H C H 2O H
when two alpha
O H H
glucose molecules H H
H H
undergo a H H
O H O H
condensation H O O H HO O H
reaction and form H O H H O H
a glycosidic bond
between the two G LUCO SE G LUCO SE
molecules
- H2O condensation reaction
6 6
C H 2O H C H 2O H
H 5 O H H 5 O
4
H 1 4
H 1 MALTOSE
O H H O O H H
HO 3 2 3 2 O H
H H O H
1 4α glycosidic bond
MALTOSE IS A DISACCHARIDE FORMED WHEN TWO ALPHA
GLUCOSE MOLECULES ARE COVALENTLY BONDED TOGETHER
 REDUCING SUGARS
All the monosaccharides and many of the disaccharides are
REDUCING SUGARS
Benedict’s test is used to determine the reducing properties of the
different sugars

Benedicts solution is a turquoise solution

containing copper ions and sodium
hydroxide; the copper ions exist as Cu2+
in this reagent
If a sugar is a reducing sugar then the Cu2+
(Cupric ions)

ions are reduced to Cu+ (Cuprous) which, in the

presence of alkaline sodium hydroxide,
Copper oxideform copper oxide
is insoluble and precipitates
out of the solution as a brick-red
precipitate
 REDUCING SUGARS

When Benedicts test is performed with the disaccharides maltose and

sucrose, the following result is obtained:

Sucrose is a Maltose is a
non-reducing sugar reducing sugar

SUCROSE MALTOSE
RESULT RESULT
 REDUCING SUGARS
Why is sucrose a non-reducing sugar?
6 6
C H 2O H C H 2O H
H 5 O H H 5 O
4 H 1 4
H 1
O H H O O H H
HO 3 2 3 2 O H 6

H O H H O H
MALTOSE 5
Sugars reduce Benedicts solution when the anomeric 4 1
carbon atom is made available to reduce the copper 3 2
ions in the solution
The anomeric carbon atom is the carbon of the
carbonyl group present in the straight chain form 6
H C O
1
of the sugar
2
H C O H
5 2
H O
3
C H The anomeric carbon atom for glucose 4 3
4
is carbon 1 1
H C O H
5
H C O H
6
SUCROSE
H C O H

H
 REDUCING SUGARS
Why is sucrose a non-reducing sugar?
6 6
C H 2O H C H 2O H
H 5 O H H 5 O
4 H 1 4
H 1
O H H O O H H
HO 3 2 3 2 O H 6

H O H H O H
MALTOSE 5
Sugars reduce Benedicts solution when the anomeric 4 1
carbon atom is made available to reduce the copper 3 2
ions in the solution
H
1
H C O H 6
2
C O
3
H O C H 2
5
H
4
C O H The anomeric carbon atom for fructose 4 3
is carbon 2 1
5
H C O H

H
6
C O H Fructose bonds to glucose to form SUCROSE
H sucrose
 Why is sucrose a non-reducing sugar?
This potential anomeric carbon
atom is unavailable This potential anomeric carbon
6 6 atom is available to reduce
C H 2O H C H 2O H
Benedict’s reagent
H 5 O H H 5 O
4 H 1 4
H 1
O H H O O H H
HO 3 2 3 2 O H 6

H O H H O H
MALTOSE 5
4 1
When maltose is boiled with Benedict’s reagent, the 3 2
region of the ring containing the anomeric carbon
atom (carbon 1) may open exposing a carbonyl
group capable of reducing Benedicts reagent – ONLY 6
AN ANOMERIC CARBON ATOM THAT IS NOT
INVOLVED IN THE FORMATION OF THE
5 2
GLYCOSIDIC BOND MAY BE EXPOSED
4 3
1
The one available anomeric carbon atom is sufficient
for this molecule to reduce Benedict’s solution and SUCROSE
thus MALTOSE is a reducing sugar
 Sucrose is formed when glucose forms a glycosidic bond
with fructose H
1
H C O H
6 The anomeric carbon
glucose atom for fructose
2
C O
5 is carbon 2 3
H O C H
4 1
4
3 2 H C O H
5
glycosidic H C O H
6 bond 6
H C O H

H
5 2 The anomeric carbon 1
atom for glucose H C O
4 3
1 is carbon 1 2
fructose H C O H
3
SUCROSE H O C H

As both the anomeric carbon atoms are involved in forming H

4
C O H
the glycosidic bond when glucose and fructose join, 5
there are no potentially free anomeric carbon atoms available H C O H
to reduce Benedict’s solution 6
H C O H
SUCROSE IS A NON-REDUCING SUGAR
H
 TEST FOR SUCROSE
In order to determine if sucrose is present in a sample or solution then the
following procedure is performed;
The sample or solution under consideration is boiled for at least fifteen minutes
in hydrochloric acid
Boiling in acid breaks glycosidic bonds – the glycosidic bond is hydrolysed
This procedure is called ACID HYDROLYSIS
The solution is then neutralised by adding drops of alkali while testing
with pH paper
Benedict’s test is now performed on the resulting solution
If a brick-red precipitate forms then sucrose was present in the original solution
Acid hydrolysis breaks the glycosidic bonds in the sucrose molecules
releasing free glucose and free fructose into the solution
Glucose and fructose are both monosaccharides and therefore reducing sugars
If no precipitate is obtained then sucrose was not present in the original sample
The need to neutralise the solution following acid hydrolysis is due to the
fact that the Benedict’s test requires an alkaline medium
 POLYSACCHARIDES
Polysaccharides are large polymers of the monosaccharides
Unlike monosaccharides and disaccharides, polysaccharides are either
insoluble or form colloidal suspensions

The principal storage polysaccharides are STARCH AND GLYCOGEN

Starch is a polymer of alpha glucose and is, in fact, a mixture of

two different polysaccharides – AMYLOSE AND AMYLOPECTIN

AMYLOSE – long unbranched chain of glucose

units
STARCH

AMYLOPECTIN – highly branched polymer

of glucose units
 CH2OH 6CH OH CH2OH CH2OH CH2OH
2
O 5 O H O H O H H O H
H H H H H
H H H H H
OH H 1 4 OH H 1 OH H OH H OH H
O O O O OH
OH 2
3
H OH H OH H OH H OH H OH
amylose

Polysaccharides:
Plants store glucose as amylose or amylopectin, glucose polymers
collectively called starch.
Glucose storage in polymeric form minimizes osmotic effects.
Amylose is a glucose polymer with α(1→4) linkages.
The end of the polysaccharide with an anomeric C1 not involved in a
glycosidic bond is called the reducing end.
Soluble in water, formed of 300-400 glucose units.
End of the chain have reducing property.
 CH2OH CH2OH
H O H H O H amylopectin
H H
OH H OH H 1
O
OH
O
H OH H OH

CH2OH CH2OH 6 CH2 CH2OH CH2OH

H O H H O H H 5 O H H O H H O H
H H H H H
OH H OH H OH H 1 4 OH H OH H
4 O O
O O OH
OH 2
3
H OH H OH H OH H OH H OH

Amylopectin is 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.
The branches produce a compact structure & provide multiple chain
ends at which enzymatic cleavage can occur.
Insoluble in water
Partially digested form is called dextrin.
 CH2OH CH2OH
H O O
glycogen
H H H
H H
OH H OH H 1
O
OH
O
H OH H OH

CH2OH CH2OH 6 CH2 CH2OH CH2OH

H O H H O H H 5 O H H O H H O H
H H H H H
OH H OH H OH H 1 4 OH H OH H
4 O O
O O OH
OH
3 2
H OH H OH H OH H OH H OH

Glycogen, the glucose storage polymer in animals, is

similar in structure to amylopectin.
But glycogen has more α(1→6) branches.
The highly branched structure permits rapid glucose release
from glycogen stores, e.g., in muscle during exercise.
The ability to rapidly mobilize glucose is more essential to
animals than to plants.
 AMYLOSE STRUCTURE

Amylose is formed by a series of condensation reactions that bond

alpha glucose molecules together into a long chain
forming many glycosidic bonds

C H 2O H C H 2O H C H 2O H
H O H H O H H O H
H H H
O H H O O H H O OH H O
HO
H O H H O H H OH
G LUCO SE G LUCO SE G LUCO SE

The amylose chain, once formed, coils into a helix

AMYLOSE STRUCTURE

O
O
O

O
O

O
O

O
O
O
O

O
O
O
O
O

O
O

O
O
O
O

O
O
O
O
O

O
O

O
O
O

THE AMYLOSE HELIX

 AMYLOPECTIN STRUCTURE
Amylopectin consists of a straight chain of alpha glucose units with branch points
occurring at approximately every twelth glucose unit along the straight chain
The branch points form when carbon 6 of a glucose molecule in the straight chain
forms a glycosidic bond with carbon 1 of a glucose molecule positioned above
the chain
C H 2O H C H 2O H
H O H H O H
H H 1
OH H O O H H
HO
B r a n c h p o in t
H OH H O H O 1 6 g ly c o s id ic b o n d
G LUCOSE G LUCOSE
6
C H 2O H C H 2O H CH 2

H O H H O H H O H
H H H
OH H O OH H O OH H O
HO
H O H H O H H O H
G LUCO SE G LUCO SE G LUCO SE

1 4 c h a in
 AMYLOPECTIN STRUCTURE

This highly branched amylopectin molecule is wrapped around the amylose to

make up the final starch molecule
This large insoluble molecule with branch points that allow for easy
access for enzymes when breaking down the molecule, makes
starch an ideal food storage compound
 REACTION BETWEEN STARCH AND IODINE SOLUTION
When iodine solution is added to a suspension of starch, the iodine
molecules pack inside the amylose helix to give a blue-black colour

When iodine reacts with the starch in a

piece of bread, the bread itself develops
the blue-black colour

N.B. Iodine is virtually insoluble in water – ‘Iodine Solution’ is really

iodine dissolved in an aqueous solution of Potassium Iodide (KI)
 GLYCOGEN

GLUCOSE IS STORED AS GLYCOGEN IN

LARGE AMOUNTS IN BOTH THE LIVER
AND SKELETAL MUSCLES
 GLYCOGEN
Glycogen is often referred to as animal starch
Glycogen has the same overall structure as amylopectin but
there is significantly more branching in this molecule

C H 2O H C H 2O H
More of these
H O H H O H branch points form
H H 1
O H H O O H H
HO
B r a n c h p o in t
H O H H O H O 1 6 g ly c o s id ic b o n d
GLUCO SE GLUCOSE
6
C H 2O H C H 2O H CH 2

H O H H O H H O H
H H H
O H H O O H H O OH H O
HO
H OH H OH H OH
G LUCO SE GLUCO SE GLUCOSE

1 4 c h a in
 STRUCTURAL POYSACCHARIDES
Cellulose is one of the most important structural polysaccharides as it is the
major component of plant cell walls
Cellulose is a polymer of beta glucose units where each glucose molecule
is inverted with respect to its neighbour
6 6
CH2OH H OH CH2OH H OH
H 5 O 3 2 5 O 3 2
O OH H O OH H
H 4 1 H 4 1
4
OH H
1 H O 4
OH H
1 H
HO 3 2 5 3 2 5 O
O
H OH 6
CH2 OH H OH 6
CH2 OH
GLUCOSE GLUCOSE GLUCOSE GLUCOSE

1 4 glycosidic bonds

The orientation of the beta glucose units places many hydroxyl (OH) groups
on each side of the molecule
Many parallel chains of beta glucose units form and each chain forms hydrogen
bonds between the OH groups of adjacent chains
 STRUCTURAL POYSACCHARIDES

The bundles of parallel chains forming hydrogen bonds

with each other creates a molecule that confers rigidity
and strength to the structures of which they form a part

hydrogen bonds between parallel chains of beta glucose

The rigidity and strength of plant cell walls is a consequence

of the incorporation of cellulose into their structure
 STRUCTURAL POYSACCHARIDES

CHITIN
Chitin is a polysaccharide forming the exoskeletons of many
invertebrates. It is a polymer of N-acetylglucosamine in beta 1 to
4 glycosidic linkage. It is the major element in the exoskeleton of
insects and crustacea where it affords protection and support.

N -A c e ty lg lu c o s a m in e
 Benedict’s Reagent
Sucrose (table sugar) contains two sugars
(fructose and glucose) joined by their glycosidic
bond in such a way as to prevent the glucose
isomerizing to aldehyde, or the fructose to alpha-
hydroxy-ketone form.
Sucrose is thus a non-reducing sugar which does
not react with Benedict's reagent..
The products of sucrose decomposition are
glucose and fructose, both of which can be
detected by Benedict's reagent.
• The Benedict’s test is used to differentiate
between reducing and nonreducing sugars.
• In the test, Cu2+ is reduced to Cu+ and the
reducing sugar is oxidized to a carboxylic acid
• The appearance of copper (I) oxide, which is
brick red, confirms the sugar to be a reducing
sugar.
• Nonreducing sugars do not react.
• Iodine Test
• The iodine test is used to differentiate between starch and
glycogen.
• Starch contains amylose, a polymeric chain of glucose residues
bonded together by a-1,4’ linkages. Amylose form an a-helix.
• Molecular iodine can intercalate into the a-helical structure. The
resulting complex is bluish black.
• The extensive branching of glycogen deters the formation of an
a-helix. The addition of molecular iodine to a solution of
glycogen does not give a bluish black color; instead, the color of
the solution is reddish purple
• Osazone Formation
• Osazones are formed by the reaction of a sugar with
phenylhydrazine.

• An osazone is a solid derivative of a sugar containing two

phenylhydrazone moieties. From the observation
of the rate at which the osazone forms and the appearance
of the precipitate can differentiate between
• epimeric sugars.
• Osazones form at different rates for different sugars:
fructose reacts very rapidly, while glucose takes longer to
react. The appearance of the precipitate can also be
different.
• The crystalstructure ranges from coarse (for glucose) to
very fine (for arabinose).
• Barfoed’s Test
• The Barfoed’s test also differentiates between
reducing and nonreducing sugars, but because
it is more sensitive than the Benedict’s test,
• it can be used to differentiate between
reducing monosaccharides and reducing
disaccharides.
• The reduction of Cu2+ to copper (I) oxide
occurs more rapidly for monosaccharides than
for disaccharides.
 Acknowledgements

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