In the name of God

Carbohydrates

SUGAR

Dr. M. Borji (CLS, PhD)

 Carbohydrates

• carbohydrates are the most abundant biomolecules on Earth.

• What is the biological importance of carbohydrates?

 Carbohydrate Functions
• Carbohydrates provide the majority of energy in most organisms.

• Carbohydrates are structural components of cell membrane

• Carbohydrate serve as metabolic intermediates ( glucose – 6 phosphate)

• Carbohydrates (ribose, 2-deoxy ribose) are component of the nucleotides
that form DNA, RNA.

• Carbohydrates play roles in cellular intercommunication, immunity

Chemical Structure
• In scientific literature, the term "carbohydrate" has many synonyms,
like "sugar" (in the broad sense), "saccharide", "glucide", "hydrate of
carbon" or "polyhydroxy compounds with aldehyde or ketone".

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
Chemical Structure, Cont………..

• Carbohydrates are made of carbon, hydrogen, and oxygen

atoms, always in a ratio of 1:2:1

• Many, but not all, carbohydrates have the empirical formula

(C H2O)n. Some also contain nitrogen, phosphorus, or
sulfur.
 Carbohydrate Classification
Monosaccharides - simple sugars with multiple OH
groups. Based on number of carbons (3, 4, 5, 6, 7), a
monosaccharide is a triose, tetrose, pentose or hexose,
heptose.

Oligosaccharides - a few (2-6) monosaccharides

covalently linked.

Polysaccharides - polymers consisting of chains of

monosaccharide or disaccharide units.
 Monosaccharides

Aldoses (e.g., glucose) have Ketoses (e.g., fructose) have

an aldehyde group at one a keto group, usually at C2.
end.

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
Representative Monosaccharides
 Functional group
Aldehyde Ketone
3 Triose Trilose
4 Tetrose Tetrulose

5 Pentose Pentulose

6 Hexose Hexulose

7 Heptose Heptulose
Monosaccharaides Have Asymmetric
Centers
• All the monosaccharides except dihydroxyacetone contain one
or more asymmetric (chiral) carbon atoms and thus occur in
optically active isomeric forms.
• Glucose (+), Fructose (-)
 Cont.……….
• The simplest aldose, glyceraldehyde, contains one chiral canter
(the middle carbon atom) and therefore has two different optical
isomers, or enantiomers.
 D and L

D & L designations are based on the

configuration about the single
asymmetric C in glucose.

• Fischer Projections.
Epimers are carbohydrates that differ in the location of the -OH
group in one location.
Mannose and Galactose are epimers of Glucose
Epimerase is a convert enzyme ( Gal to Glu) in Liver.
Chemical properties of monosaccharide
• Osazone Formation • Oxidation
• By phenylhydrazine (PhNHNH2) • Gluconic acid
• specific Osazone crystal for • Glucuronic acid
every monosaccharide • Glucosaccharic acid

 Sugars as reducing agent

• To Reduce
•

Fehling and Benedict test

 1
CH2OH

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 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 CH 2OH 6 CH 2OH
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 b-D-glucose

Cyclization of glucose produces a new asymmetric center at

C1. The 2 stereoisomers are called anomers,  & b.
Haworth projections represent the cyclic sugars as having
essentially planar rings, with the OH at the anomeric C1:
  (OH below the ring)
 b (OH above the ring)
 Carbohydrate derivatives

COOH CHO
CH2OH
H C OH H C OH
H C OH
HO C H HO C H
H C OH
H C OH H C OH
H C OH
H C OH H C OH
CH2OH
CH2OH COOH
D-ribitol
D-gluconic acid D-glucuronic acid

sugar alcohol - lacks an aldehyde or ketone; e.g., ribitol.

sugar acid - the aldehyde at C1, or OH at C6, is oxidized
to a carboxylic acid; e.g., gluconic acid, glucuronic acid.
 Carbohydrate derivatives
CH2OH CH2OH

H O H H O H
H H
OH H OH H
OH OH OH O OH
H NH2 H N C CH3
H
-D-glucosamine -D-N-acetylglucosamine

amino sugar - an amino group substitutes for a

hydroxyl. An example is glucosamine.
The amino group may be acetylated, as in N-
acetylglucosamine.
 O H

H3C C NH O COO
R HC OH
H H R=
HC OH
H OH
CH2OH
OH H
N-acetylneuraminate (sialic acid)

N-acetylneuraminate (N-acetylneuraminic acid, also called sialic acid) is

often found as a terminal residue of oligosaccharide chains of
glycoproteins.
Sialic acid imparts negative charge to glycoproteins, because its carboxyl
group tends to dissociate a proton at physiological pH, as shown here.
Carbohydrate derivatives
 Oligosaccharides
• is a saccharide polymer containing a small number (typically 2 to 6)
of monosaccharides (simple sugars).

A disaccharide consists of two sugars • Maltose comes from the

joined by an O-glycosidic bond. hydrolysis of large polymeric
oligosaccharides such as starch
The three common Disaccharides are: and glycogen and is in turn
• Maltose (1 4)αglu+ α glu hydrolyzed to glucose by
• Lactose (1 4)β glu+ β gal .
• Sucrose (1 2) α glu+ β fru
 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
(1 4) glycosidic 6 CH 2OH

5
6 CH 2OH

O 5 O OH
link between C1 - C4 H
H
H
H
OH of 2 glucoses. 4
OH H 1 O 4
OH H 1

H
It is the  anomer OH H
3 2 3 2

H OH H OH
(C1 O points down). cellobiose
Cellobiose, The b(1 4) glycosidic linkage is represented as
a zig-zag,
 Reducing Properties of Disaccharides

Disaccharides with 1,4 linkage are reducing because they have a free

aldehyde group in one of the two monosaccharides.

Lactose & maltose are reducing sugars.

Sucrose with 1,2 linkage, no aldehyde or ketone group is free,

therefore sucrose is a non reducing sugar

 Polysaccharides
 Contain many linked monosaccharides and vary in chain length and
molecular weigh.
 The monosaccharide units may be linked linearly, or the chains may
be branched.
 Polysaccharides formed from Glucose.
 Is the energy-storing carbohydrate of plants. It is the form in which glucose is
stored by plants for later use.
 Is made up of glucose units joined mainly by 1,4-α-glycosidic bonds, although
the chains may have a number of branches attached through 1,6- α –glycosidic
bonds.

Starch can be separated into two fractions:

amylose and amylopectin.
In amylose, which constitutes about 20% of starch, the glucose units
(50 to 300) are in a continuous chain, with 1,4 linkages
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
 is highly branched.
• May contain 300 to 5000 glucose units,
• Chains with consecutive 1,4 links average only 25 to 30 units in
length.
• These chains are connected at branch points by 1,6 linkages.
• Because of this highly branched structure, starch granules swell and
eventually form colloidal systems in water.
• Is the energy-storing carbohydrate of animals.
• Like starch, it is made of 1,4- and 1,6-linked glucose units.
• Glycogen has a higher molecular weight than starch (perhaps
100,000 glucose units), and its structure is even more branched
than that of amylopectin, with a branch every 8 to 12 glucose units.
• Glycogen is produced from glucose, transported to the liver,
muscles, where it is stored for later use.
• Glycogen helps maintain the glucose balance in the body by
removing and storing excess glucose from ingested food and later
supplying it to the blood when various cells need it for energy.
 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 is an unbranched polymer of β-glucose joined by 1,4-β-

glycosidic bonds.
 a major constituent of plant cell walls.
 The role of cellulose is to impart strength and rigidity to plant cell
walls.
Dextrin: Produced during incomplete hydrolysis of starch or glycogen.
Glycosaminoglycans (mucopolysaccharides) are linear polymers of
repeating disaccharides.
i. The constituent monosaccharides tend to be modified, with acidic
groups, sulfated hydroxyl and amino groups, etc.
ii. Glycosaminoglycans tend to be negatively charged, because of the
prevalence of acidic groups.
iii. Also are found in the Extracellular matrix.
 CH2OH
D-glucuronate 6
 H 5 O
6COO H
4 1 O
O H
H 5
H OH H
4 H 1 3 2
OH
H H NHCOCH3
3 2 O
H OH N-acetyl-D-glucosamine
hyaluronate

Hyaluronate (hyaluronan) is a glycosaminoglycan with a repeating

disaccharide consisting of 2 glucose derivatives, glucuronate
(glucuronic acid) & N-acetyl-glucosamine. The glycosidic linkages
are β(13) & β(14).
Heparin, a soluble glycosaminoglycan
found in granules of mast cells, has a
structure similar to that of heparan sulfates,
but is more highly sulfated.
When released into the blood, it inhibits clot
formation by interacting with the protein
antithrombin.
Thank you for your attention