DISACCHARIDES

4th lec.1st year MBBS.

IMDC
 disaccharide
• consist of two monosaccharides joined
covalently by an O-glycosidic bond,
which is formed when a hydroxyl
group of one sugar reacts with the
anomeric carbon of the other. This
reaction represents the formation of an
acetal from a hemiacetal (such as
glucopyranose) and an alcohol (a hydroxyl
group of the second sugar molecule).
• N-glycosyl bonds join the anomeric carbon
of a sugar to a nitrogen atom in
glycoproteins and nucleotides
• Glycosidic bonds are readily hydrolyzed by
acid but resist cleavage by base.
• General formula is C12 H22 O11
maltose
 maltose

• Malt sugar
• Reducing
• Shows mutarotation
• Osazone formation(sun flower like)
• Sweet sugar , soluble in water
• Sources = starch, baby foods, cereals
isomaltose
Trehalose
 Trehalose
• a disaccharide of D-glucose that, like
sucrose, is a nonreducing sugar.
• No mutarotation
• is a major constituent of the
circulating fluid (hemolymph) of
insects, serving as an energy-
storage compound.
• Also found in fungi & yeast
•
lactose
• -D- Galactopyranosyl
(1-4)α-D-
glucopyranoside
• Milk sugar, about
5%.
• At body temp-, a
mixture of both α
and β form in 2:3
ratio
• Synthesized by secr-
cells
 lactose
• Dextrorotatory
• Reducing
• Can form osazone (powder puff or
hedge hoge)
• Shows mutarotation
• Hydrolyzed by “Lactase”
• Lactose intolerance
•
 lactulose
• Galactose + Fructose
• Through β C1 of galactose and C4 of
fructose
• Neither absorbed nor broken down
• NH3 intoxication
sucrose
 sucrose
• Table sugar
• Sources
• Very soluble & very sweet
• Non reducing
• No osazone formation
• No mutarotation
• Dextrorotatory
• Invert sugar
 Cleavage of Sucrose
(α -glucosidase or invertase)
CH 2OH
O
H H HOCH 2 O H
H
OH H H HO
HO O CH2 OH

H OH OH H

H2 O

CH 2OH
O HOCH 2 O H
H H
H H HO
OH H H CH2 OH
HO OH
OH H
H OH

Glucose Fructose
 Reducing end of sugars
• The oxidation of a sugar’s anomeric carbon
by cupric or ferric ion (the reaction that
defines a reducing sugar) occurs only with
the linear form, which exists in equilibrium
with the cyclic form(s).
• When the anomeric carbon is involved in a
glycosidic bond, that sugar residue cannot
take the linear form and therefore
becomes a nonreducing sugar.
• In describing disaccharides or
polysaccharides, the end of a chain with a
free anomeric carbon (one not involved in
a glycosidic bond) is commonly called the
reducing end.
 Artificial sweetners
• Secharine
• Aspartame(L-aspartyl L-
phenylalanine)
Saccharin(benzoic sulfimide)
C7H5NO3S
 oligosaccharides
• Oligosaccharides are short polymers of several
monosaccharides joined by glycosidic bonds.
At one end of the chain, the reducing end, is a
monosaccharide unit whose anomeric carbon is
not involved in a glycosidic bond
• contain from 3 to roughly 12 monosaccharides
linked together.
• They are often found attached through N- or O-
glycosidic bonds to proteins to form
glycoproteins. (O2 atom of serine or
threonine by o- linkage, nitrogen of aspargine
by N- glycosidic)
• Integral membrane proteins contains covalently
attached units on their extracellular face.
• Many secreted proteins e.g. antibodies,
coagulation factors contain .
• Helps in molecular targeting & cell-cell
recognition
• Required for endocytosis.
 POLYSACCHARIDES
• Most carbohydrates found in nature occur
as polysaccharides, polymers of medium
to high molecular weight.
• also called glycans, differ from each
other in the identity of their recurring
monosaccharide units, in the length of
their chains, in the types of bonds linking
the units, and in the degree of branching.
• Homopolysaccharides
contain only a single type of monomer;

• heteropolysaccharides
contain two or more different kinds
Complex Carbohydrates
• Cellulose
 Most abundant carbohydrate on the
planet!
– Component of plant cell walls
– Indigestible by animals
• β 1-4 bonds


• Starch
– Energy storage molecule in plants
– Can be digested by animals
• α 1-6 bonds
 Cellulose
• Cellulose is a linear
polysaccharide in which
some 1500 glucose
rings link together. It is
the chief constituent of
cell walls in plants.
• Human digestion cannot
break down cellulose for
use as a food, animals
such as cattle and
termites rely on the
energy content of
cellulose. They have
protozoa and bacteria
with the necessary
enzymes in their
digestive systems. Only
animals capable of
breaking down cellulose
are tunicates.
 Starches
• Starches are carbohydrates in
which 300 to 1000 glucose
units join together. It is a
polysaccharide used to
store energy for later use.
Starch forms in grains with
an insoluble outer layer
which remain in the cell
where it is formed until the
energy is needed. Then it
can be broken down into
soluble glucose units.
Starches are smaller than
cellulose units, and can be
more readily used for
energy. In animals, the
equivalent of starch is
glycogen, which can be
stored in the muscles or in
the liver for later use.
•
• α-1,6 bonds
• Glycogen
 polysaccharides can be linked to other
molecules to form glyco-proteins and glyco-lipids
 Glycoproteins
Some examples

• Polysaccharide component of antibodies has

major effect on antibody function


• Polysaccharides attached to proteins on

surface of red blood cells (RBC) determine
blood type (A,B,O)


• Polysaccharides are attached to proteins in

the Golgi apparatus through a process of
post-translational modification
•
• Different types of cells do different post-
tranlational modifications
– More about this later
 Glycolipids
• Polysaccharides can also be attached to lipid
molecules

•An outer-membrane constituent of gram negative bacteria, LPS, which includes O-

antigen, a core polysaccharide and a Lipid A, coats the cell surface and works to
exclude large hydrophobic compounds such as bile salts and antibiotics from
invading the cell. O-antigen are long hydrophilic carbohydrate chains (up to 50
sugars long) that extend out from the outer membrane while Lipid A (and fatty acids)
anchors the LPS to the outer membrane.
 Glycolipids

• Polysaccharides
(blue) are also
used in animal
cells to link
surface proteins
and lipid anchors
to the
membrane.