CARBOHYDRATE METABOLISM

Structure

March 5, 2013
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Outline
Di and oligosaccharides
Polysaccharides
Homo and heteropolysaccharides
Glycoconjugates

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Disaccharides: Sucrose
Sucrose is formed by linking a Dglucose with b D-fructose to give a 1,2
glycosidic link.
CH2OH
H
H
OH

O H HO 2CH2
1
H

HO
H

OH

H
OH

HO
H

CH2OH
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Disaccharides: Lactose
Lactose is formed by joining b Dgalactose to a D-glucose to give a 1,4
glycoside

CH2OH
HO
H

CH2OH

O
H
OH

OH

b D-galactose

O H

H
1

O
H

H
4
OH
H

OH

OH

a D-glucose

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Disaccharides: Maltose
Maltose is formed by linking two a-Dglucose molecules to give a 1,4
glycosidic link.

CH2OH

CH2OH
H
HO

H
OH
H

O H
H

OH

O H
H
OH

OH

OH

4-O-a-D-glucopyranosyl-a-D-glucopyranose

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Oligosaccharide
An oligosaccharide is a saccharide polymer
containing a small number (typically three to
ten of component sugars, also known as
simple sugars. The name derived from the
Greek oligos, meaning "a few".
Fructo-oligosaccharides (FOS), which are
found in many vegetables, consist of short
chains of fructose molecules. Inulin has a
much higher degree of polymerization than
FOS and is a polysaccharide
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Oligosaccharide
Fructooligosaccharides (FOS) also
sometimes called oligofructose or
oligofructan, is a class of
oligosaccharides used as an artificial
or alternative sweetener
Two different classes of FOS mixtures
are produced commercially, based on
inulin degradation or processes
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Oligosaccharide-Inulin
Inulins are a group of naturally occurring
polysaccharides (several simple
sugars linked together) produced by
many types of plants. They are belong
to a class of fibers known as fructans.
Inulin is used by some plants as a
means of storing energy and is
typically found in roots or rhizomes.
Most plants which synthesize and store
inulin do not store other materials such
as starch
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Polysaccharides: Cellulose
Cellulose is the major structural
polymer in plants. It is a liner
homopolymer composed of b Dglucose units linked b-1,4. The
repeating disaccharide of cellulose
is b-cellobiose.
Animals lack the enzymes
necessary to hydrolyze cellulose.
The bacteria in ruminants (eg.
cows) can digest cellulose so that
they can eat grass, etc.
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Polysaccharides: Starch
Starches are storage forms of glucose
found in plants.
They are polymers of a linked glucose.
If the links are only 1,4, the polymer is
linear and is called amylose.
Amylose usually assumes a helical
configuration with six glucose units
per turn.
If the links are both 1,4 and 1,6, the
polymer is branched and is called
amylopectin.
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Polysaccharides: amylose/amylopectin
H

H
OH
H

O H
H

OH

H
OH

O H
H

H
OH
H

OH

OH

O H
H

OH

O H
H
OH

OH

OH

CH2OH

CH2

O H
H

H
OH

Amylopectin
1,6 link at branch

H
OH

O H

amylose

H
OH
CH2OH

O H
H

H
OH

H
OH
CH2OH
H

CH2OH

CH2OH
H

O H
H
OH

CH2OH

CH2OH

CH2OH

CH2OH

H
O

H
OH
H

O H
H
OH

O H
H
OH

OH

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Polysaccharides: glycogen
The storage carbohydrate in animals
is glycogen. It is a branched chain
polymer like amylopectin but it has
more frequent branching (about
every 10 residues). Glycogen is
stored in liver and muscle cells.
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Polysaccharides
Bacterial cell walls have
heteropolysaccharides as major
components.

The polymers consist of chains of

alternating N-acetyl-b-D-glucosamine
and N-acetylmuramic acid (next slide).
The parallel chains are linked by short
peptide residues.
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Polysaccharides

CH2OH
O OH
H
H
O
H
HO
H
CH3CH H HN C CH3
O
COO
N-acetyl muramic acid

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Glycoconjugates
Glycoconjugates are compounds that
covalently link carbohydrates to
proteins and lipids.
Proteoglycans and glycoproteins are
two kinds of glycoconjugates that
contain protein.

Proteoglycans:
Proteoglycans have a very high
carbohydrate to protein ratio, often
95:5, and are found in the extracellular
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matrix.

Glycoproteins
These materials contain carbohydrate
residues on protein chains.
Important examples of glycoprotein are
antibodies-chemicals which bind to
antigens and immobilize them.

The carbohydrate part of the

glycoprotein plays a role in
determining the part of the antigen
molecule to which the antibody binds.

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Glycoproteins:
The human blood groups A, B, AB,
and O depend on the
oligosaccharide part of the
glycoprotein on the surface of
erythrocyte cells.

The terminal monosaccharide of the

glycoprotein at the nonreducing
end determines blood group.
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Glycoproteins:
Type
A
B
AB
O

Terminal sugar
N-acetylgalactosamine
a-D-galactose
both the above
neither of the above

O is the universal donor

AB is the universal acceptor

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Reducing and Nonreducing Sugar

Sugars which are capable to reduce the
oxidizing agents such as Tollen
reagents(AgO), Fehling reagents(CuO)
called the Reducing Sugars.
Examples: glucose, fructose, maltose,
lactose etc
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Reducing sugar
A reducing sugar is any sugar that, in basic
solution, forms some aldehyde or ketone.
This allows the sugar to act as a reducing
agent, for example in the Maillard reaction
and Benedict's reaction.

Those sugar which are unable to reduce

the such above oxidizing agents is
called the Non-reducing sugars.
Examples: Sucrose, Trehalose

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Maillard Reaction:
The Maillard reaction is a chemical reaction
between an amino acid and a reducing
sugar. Like caramelization (is the oxidation
of sugar), it is a form of non-enzymatic
browning
-This reaction is the basis of the flavoring
industry, since the type of amino acid
determines the resulting flavor.
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The End
Carbohydrates II
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