CARBOHYDRATES

General Information
CHO= Aldehyde
C=O = Ketones
R-COO-R= Ester
OH= Alcohol
R-COOH= Carboxyl Acid
What are Carbohydrates??
They are hydrates of Carbon
Made up of Carbon, hydrogen, Oxygen
They are polyhydroxyaldehyde or ketones or
compounds which produce them on
hydrolysis.
Sugar- mean carbohydrates soluble in water
and sweet in taste.
Carbohydrates (glycans) have the
following basic composition:
I
(CH2O)n or H - C - OH
I
FUNCTIONS
Source of energy (4Cal/grams)
 They are structure of cell membrane and
cellular functions such as cell growth, adhesion
and fertilization
 They are structural components of many
organisms. i.e. fiber (cellulose) of plants,
exoskeleton of some insects and the cell wall of
microorganisms.
Precursors for many organic compounds (fats,
amino acids).
 Serve as the storage form of energy
(glycogen) to meet the immediate energy
demands of the body.
CLASSIFICATION

 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.
(Homopolysaccharides and
Heteropolysaccharides)
 Monosaccharides
Aldoses (e.g., glucose) Ketoses (e.g., fructose)
have an aldehyde group have a keto 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
Based on Number of Carbon atom
Monosacccharides are classified as:
Triosis(3C)
Tetroses(4C)
Pentoses (5C)
Hexoses (6C)
Heptoses (7C)

What will be Glucose and Fructose??????

Monosaccharides Aldoses Ketoses

Trioses Glyceraldehyde Dihydroxyacetone

Tetroses Erythrose Erythrulose

Pentoses Ribose Ribulose

Hexoses Glucose Fructose

Heptoses Glucoheptose Sedoheptulose

 Stereoisomerism is an important
character of monosaccharides.
Stereoisomers are the compounds
that have the same structural
formulae but differ in their spatial
configuration.
 Glyceraldehyde has one
asymmetric carbon atom
therefore it exists as two
stereoisomers.
 The number of asymmetric
carbon atoms (n) determines the
possible isomers of a given
compound which is equal to 2
raise to n.

Enantiomers
Enantiomers are a special type of
stereoisomers that are mirror
images of each other.
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
D-glyceraldehyde L-glyceraldehyde
asymmetric C in
glyceraldehyde. CHO CHO

The lower H C OH HO C H
representations are CH2OH CH2OH
Fischer
Projections. D-glyceraldehyde L-glyceraldehyde
Optical activity of Sugars
Optical activity is a characteristic feature of
compounds with asymmetric carbon atom.
When a beam of polarized light is passed
through a solution of an optical isomer, it will
be rotated either to the right or left.
The term dextrorotatory (+) and levorotatory
(-)
Epimers
If two monosaccharides differ from each other
in their configuration around a single specific
carbon (other than anomeric) atom.
Hemiacetal & hemiketal formation

H H
An aldehyde
can react with C O + R' OH R' O C OH
an alcohol to R R
form a aldehyde alcohol hemiacetal
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
The hydroxyl group of monosaccharides can react with its own aldehyde or keto
functional group to form hemiacetal and hemiketal.

C1 reacts with alcohol group at C5 to form two types of cyclic hemiacetals namely alpha
and Beta
Mutarotation of Fructose
 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, a & b.
Haworth projections represent the cyclic sugars as
having essentially planar rings, with the OH at the
anomeric C1:
 a (OH below the ring)
 b (OH above the ring).
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 + C H 3 -O H HO H
H OH H OH
H OH H OCH3
 -D -glucopyranose m ethanol m ethyl- -D -glucopyranose
OLIGOSACCHARIDES

• 2-10 Monosaccharides joined

together.

• They are joined upon hydrolysis.

• Number of Monosaccharides
define oligosaccharides

• Eg: Disaccharides (2
monosaccharides)
• Trisaccharides (3
 6 CH 2 O H 6 CH 2 O H

Disaccharide H
5 O H H
5 O H

s: 4
H
OH H 1 4
H
OH H 1

Maltose, a OH 3 2
O
3 2
OH

cleavage H OH m altose H OH

product of
6 CH 2 O H 6 CH O H
starch (e.g., 5
2

O 5 O OH
amylose), is a H
H
H
H
O
disaccharide
4 1 4 1
OH H OH H
H H
with an a(1® 4) O H 3 2 3 2

glycosidic link H OH
cellobiose
H OH

between C1 - C4
Cellobiose, a product of cellulose breakdown, is the
OH of 2 equivalent b anomer (O on C1 points up).
otherwise
glucoses.
The b(1® 4) glycosidic linkage is represented as a zig-
zag, but one glucose is actually flipped over relative
to the other.
 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 a (O
points down from
ring), the linkage is
a(12).
Sucrose is the major carbohydrate
produced in photosynthesis.
It is transported into the storage organs of
plants (such as roots, tubers and seeds)
Sucrose is the most abundant among the
naturally occurring sugars.
It has distinct advantages over other
sugars as a storage and transport form.
This is due to the fact that in sucrose,
both the functional groups (aldehyde and
keto) are held together and protected
from oxidative attacks.
 Lactose
Lactose, milk sugar, is
composed of galactose
& glucose, with b(14)
linkage from the
anomeric OH of
galactose.
Its full name is b-D-
galactopyranosyl-(1
4)-a-D-glucopyranose
Complex Carbohydrates
Polysaccharides
long carbohydrate chains of
monosaccharides linked by glycosidic
bonds
alpha (a) bonds (starch)
beta (b) bonds (found in fiber)

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 amylose

Complex Carbohydrates
Starch amylopectin
 plant storage form of
carbohydrate
 long branched or
unbranched chains of
glucose
 amylose
 amylopectin

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Amylose
Glucose subunits.
Long unbranched
chains.
Alpha 1-4
glycosidic
linkages.
 CH 2OH CH 2 OH
H O H H O H amylopectin
H H
OH H OH H 1
O
OH
O
H OH H OH

CH 2OH CH 2OH 6 CH 2 CH 2OH CH 2OH

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

Amylopectin is a glucose polymer with mainly a(14)

linkages, but it also has branches formed by a(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.
Dextrin
Breakdown products of starch.
Enzyme- amylase
Starch is subsequently hydrolysed
through different dextrins and then
finally to glucose and maltose.
 CH 2 OH CH 2 OH
O O
glycogen
H H H H
H H
OH H OH H 1
O
OH
O
H OH H OH

CH 2 OH CH 2 OH 6 CH 2 CH 2 OH CH 2 OH
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 a(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.
 CH 2 OH 6 CH OH CH 2 OH CH 2 OH CH 2 OH
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
c e llu lo s e
Cellulose, a major constituent of plant cell walls, consists
of long linear chains of glucose with b(1®4) linkages.
Every other glucose is flipped over, due to b 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 Schematic of arrangement of
bundles - microfibrils. cellulose chains in a microfibril.
Complex Carbohydrates
Fiber
Dietary Fiber
 non-digestible carbohydrates (chains of
monosaccharides) and lignin that are intact
and intrinsic in plants (includes
oligosaccharides)
Functional Fiber
 isolated, non-digestible carbohydrates that
have beneficial physiological effects in
humans

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OXIDATION
Terminal aldehyde, keto or alcohol group gets
oxidised.
Aldehyde CHO---------COOH forms gluconic
acid
Alcohol group CH2OH-----COOH gucuronic
acid
D-Galactose--------- D- Dulcitol
D Mannose----------- D-Mannitol
D-Fructose-----------D-Mannitol+ D-
Sorbitol
D- Ribose------------D- Ribitol
The sugars that differ in these 2 carbon
configuration give same type of osazones,
since the difference is masked by binding
with phenylhydrazine.

Therefore, glucose, mannose and

fructose gives same type of osazones.
Glycoproteins
Proteins are covalently bound to
carbohydrate which are referred as
glycoproteins.
The blood group antigens contain
carbohydrates as glycoprotein or glycolipid.
The carbohydrate content plays an important
role in blood grouping.
Glycoprotein play important roles in human
body- i.e. as enzymes, hormones, transport
proteins, receptors and structural proteins.
Digestion & Absorption

1. Mouth
chewing
salivary amylase

2. Stomach
fibers remain in the
stomach longer, delays
gastric emptying

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Digestion & Absorption
Small Intestine
pancreas secretes enzyme pancreatic amylase
enzymes located on the cell membranes of the
intestinal epithelial cells complete digestion

maltase
maltose glucose + glucose

sucrase
sucrose glucose + fructose

lactase
lactose glucose + galactose
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47
Digestion & Absorption
Large Intestine
 resistant starches and fibers may be
digested by bacteria
 produces short chain fatty acids
 absorbed by the intestine and used for energy

(dietary fiber yields about 2 kcal/g)

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THANK
YOU
Assignment:
1) Biological importance of different
monosaccharides, Disaccharides and
polysaccharides.
2) Look into and learn the structures to
understand the difference in each sugar.