BIOMOLECULES

Agitha R. Menon
PGT
AECS, Indore
 Carbohydrates
• generally produced by plants
• Most have a general formula, Cx(H2O)y
(were known as hydrates of carbon)
• Ex.Glucose (C6H12O6) fits into the formula
C6(H2O)6.
• Definition: the carbohydrates are
optically active polyhydroxy aldehydes/
ketones or the compounds which produce
 How are Carbohydrates
classified?
• On their behavior towards hydrolysis,they
are divided into
 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.
 According to the functional group
present
• Aldose – If the carbohydrate contains an
aldehyde. Aldotriose – containing three
carbon atoms(Ex. Glyceraldehyde),
aldotetrose, aldopentose (Ex. Ribose),
aldohexose (Ex. Glucose)
• Ketose - If the carbohydrate contains a
ketone. Ketotriose, ketotetrose,
ketopentose, ketohexose(Ex.
Fructose)
 Monosaccharides
Aldoses (e.g., glucose) Ketoses (e.g., fructose)
have an aldehyde have a keto group,
group at one end.
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 6
 D vs L Designation
CHO CHO
D & L designations
are based on the H C OH HO C H
configuration CH2OH CH2OH
about the single
asymmetric C in D-glyceraldehyde L-glyceraldehyde
glyceraldehyde.
CHO CHO
The lower H C OH HO C H
representations are
Fischer CH2OH CH2OH
Projections. D-glyceraldehyde L-glyceraldehyde
7
 Sugar Nomenclature

For sugars with more O H O H

than one chiral C C
center, D or L refers
to the asymmetric H – C – OH HO – C – H
Carbon farthest
from the aldehyde
HO – C – H H – C – OH
or keto group. H – C – OH HO – C – H
Most naturally H – C – OH HO – C – H
occurring sugars CH2OH CH2OH
are D isomers.
D-glucose L-glucose
 As reducing or non reducing sugars
-
• All those carbohydrates which reduce
Fehling’s solution and Tollens’ reagent
are referred to as reducing sugars.
• In disaccharides, if the reducing groups
of monosaccharides i.e., aldehydic or ketonic
groups are bonded, these are non-reducing
sugars e.g. sucrose. On the other hand,
sugars in which these functional groups
are free, are called reducing sugars, for
example, maltose and lactose.
 Glucose
• Source: It is
present in sweet
fruits and
honey.
• Ripe grapes
also contain
glucose in large
amounts.
Preparation of Glucose:
 Structure of Glucose
Molecular formula C6H12O6
Glucose Reaction Reagent Products Proves that
On prolonged all the six
heating with HI, it carbon atoms
forms n-hexane are linked in a
straight chain.
Glucose reacts These reactions
with confirm the
hydroxylamine presence of a
to form an oxime
carbonyl group
and adds a
(>C = O) in
molecule of
hydrogen glucose.
cyanide to give
cyanohydrin.
 Molecular formula, C6H12O6
Glucose Reaction Reagent Products Proves that
Glucose gets the carbonyl group
oxidised to six is present as an
carbon carboxylic
aldehydic group.
acid (gluconic acid)
on reaction with a
mild oxidising
agent like
bromine water.

Acetylation of which confirms the

glucose with presence of five –
acetic anhydride
OH groups
gives glucose
attached
pentaacetate
to different carbon
atoms.
On oxidation with This indicates the
nitric acid, glucose presence
as well as gluconic
of a primary
acid both
alcoholic (–OH)
yield a dicarboxylic
acid, saccharic group in glucose.
acid.
Pentoses and CHO
hexoses can 1

cyclize as the H
2
C OH
ketone or HO C H
aldehyde reacts 3 D-glucose
with a distal OH. H C OH (linear form)
4
H C OH
5
Glucose forms an CH2OH
intra-molecular 6
hemiacetal, as the 6 CH2OH 6 CH2OH
C1 aldehyde & 5 5 O
C5 OH react, to H O H H OH
form a 6-member 4
H
OH H 1 4
H
OH H 1
pyranose ring, H
OH
named after OH
3 2
OH
3 2
pyran. H OH H OH
-D-glucose -D-glucose

These representations of the cyclic sugars

09/11/23 are called Haworth projections. 14
 6 CH 2 OH 6 CH 2 OH
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
-D -glucose -D -glucose

Cyclization of glucose produces a new asymmetric center

at C1. The 2 stereoisomers are called anomers,  & .
Haworth projections represent the cyclic sugars as
having essentially planar rings, with the OH at the
anomeric C1:
 (OH below the ring)
  (OH above the ring).
09/11/23 15
 Reactions and facts about glucose which
cannot be explained by its open chain
structure
• Despite having the aldehyde group, glucose does not give Schiff’s
test and it does not form the hydrogensulphite addition
product with NaHSO3.

• The pentaacetate of glucose does not react with hydroxylamine

indicating the absence of free —CHO group.

• Glucose is found to exist in 2 different crystalline forms which

- α and β. The α-form of glucose (m.p. 419 K) is obtained by
crystallisation from concentrated solution of glucose at 303 K while
the β-form (m.p. 423 K) is obtained by crystallisation from hot and
saturated aqueous solution at 371 K.

This behaviour could not be explained

by the open chain structure.
 Fructose
Fructose is an important ketohexose.

It is obtained along with glucose by the hydrolysis of

sucrose. CH OH
1 2

2C O

HO C H
1 CH2OH
3 HOH2C 6 O
H C OH
4 5 H HO 2

H C OH H 4 3 OH
5
OH H
6
CH2OH

D-fructose (linear) -D-fructofuranose

Fructose forms a 5-member furanose ring, by reaction

of the C2 keto group with the OH on C5.
Its two cyclic forms, α and The cyclic structures of two
β, are obtained by the anomers of fructose are
addition of -OH at C5 to the represented by Haworth
(>C=O) group. The ring, structures as given.
thus formed, is a 5
membered furanose ring.
References:

1. NCERT Class XII Chemistry Vol 2

2. Google images