DISACCHARIDES

Disaccharides are formed by joining 1 molecule of

monosacharide to another by a covalent bond known
as –o-glycosidic bond. O-glycosidic bond is formed
when a hydroxyl group of 1 sugar reacts with the
anomeric carbon of the other.
Contd.
Because monosacharides have multiple OH groups,
various glycosidic linkages are possible.
Indeed, the wide array of these linkages in concert
with the wide variety of monosaccharides and their
many isomeric forms makes complex carbohydrates
structurally diverse molecules. When an anomeric
carbon becomes involved in a glycosidic bond, it
cannot be oxidized by cuprous or ferric ions.
The sugar which its anomeric carbon is involved in
glycosidic bond no longer acts as a reducing sugar.
However, the sugar which has a free anomeric
carbon which is not involved in glycosidic bond is
known as the reducing end of the chain.
Contd.
Glycosidic bonds are readily hydrolysed by acid (but
not by base). Therefore, disaccharides can be
hydrolysed to yield their free monosaccharide
components by boiling with dilute acids.
E.g. of disaccharides that are abundantly present in
nature are maltose, lactose and sucrose.
• Maltose: Maltose is produced by hydrolysis of
starch and is in turn hydrolysed to glucose by
enzyme known as maltase.
• Maltose is made up of 2 glucose molecules
joined together by a glycosidic linkage
between the C-1 atom of 1 sugar and the
hydroxyl (oxygen) atom in C-4 of adjacent
sugar.
Contd.
The sugar on the C-1 side of the link is in the α-
configuration. Hence, the maltos linkage is called α-
1, 4-glycosidic bond.
 NB: Naming of disaccharides.
1. Start with the non-reducing end to the left.
2. Start with O- to denote that the linkage involves
oxygen.
3. Configuration is given. i.e. α or β.
4. Ring structure, wher 5 or 6 membered ring. i.e.
Furanosyl or Pyranosyl residue.
5. The 2 carbon atoms involved in linkage with arrow
connecting them.
6. Followed by the configuration of 2nd
monosaccharides.
7. Ring structure of the 2nd monosaccharide residue.
 lactose

This occurs only in milk. It consists of galactose joined

to glucose by a β-1,4-glycosidic linkage. Lactose is
hydrolysed to galactose & glucose by enzyme lactase in
humans and β-galactosidase in bacteria.

Many adults are unable to metabolize the milk sugar-

lactose and experience gastrointestinal disturbances if
they drink milk (lactose intolerance). Lactose
intolerance (hypolactasea)is most commonly caused by
a deficiency of the enzyme lactase which cleaves
lactose into glucose and galactose.
 Sucrose
Sucrose is a common table sugar and is obtained
commercially from sugar cane or beet. It is a
disaccharide of glucose and fructose. Sucrose contains
no free anomeric carbon atom. The anomeric carbon
of both monosacharide units are involved in glycosidic
bond. Sucrose is therefore not a reducing sugar and
has no reducing end.
Sucrose is a major intermediate product of
photosynthesis. In many plant s, it is the principal form
in which sugar is transported from the leaf to other
parts of plants where there are vascular systems
 Trehalose
Trehalose is another type of disaccharide made up of 2
glucose units. The anomeric carbon of both glucose
moieties are involved in glycosidic bond, therefore, it is
a non-reducing sugar like sucrose.
Trehalose is a major constituent of the circulating fluid
(haemolymph) of insects in which it serves as an energy
storage compound.
 OLIGOSACCHARIDES
• Oligosaccharides are carbohydrates built by the linkage of two or more
monosaccharides by O-glycosidic bonds.
• They are found in both prokaryotic and eukaryotic organisms, either as
naturally occurring substances or as hydrolysis products of natural
materials. Several are constituents of the sweet nectars or saps extruded
from plants and trees
• Examples are Cycloamyloses and Stachyose
• Stachyose is typical of the oligosaccharide components found in
substantial amounts in beans, peas, bran and whole grains. They are
metabolized by bacteria in the intestine (thy are not affected by digestive
enzymes) and hence the cause of flatulence that often accompanies the
consumption of these foods
• Another example is Amygdalin (found in bitter almonds and in the kernels
or pits of cherries, peaches and apricots) whose hydrolysis product yield
Laetrile (it is claimed to have some anticancer properties)
• Oligosaccharides also occur widely as
components of antibiotics derived from
various sources e.g Streptomycin. Some of
these antibiotics also show antitumor activity
e.g Bleomycin A2
 Polysaccharides and Proteoglycans

Polysaccharides
Large polymeric oligosaccharides formed by the linkage
of multiple monosaccharides are called
polysaccharides. Most of the carbohydrates found in
nature occur as polysaccharide polymers of high
molecular wt. Polysaccharides are also known as
glycans. Polysaccharides are different from each other
in:
Contd.
Polysaccharides are different from each other in:
1. The identity of their reoccurring
monosaccharide units.
2. The length of their chains.
3. The types of bonds linking the units.
4. The degree of branching.

Polysaccharides play vital role in energy storage

and in maintaining the structural integrity of an
organism. Polysaccharides can be classified into
two:
5. Homopolysaccharides.
6. Heretopolysaccharides.
 Homopolysaccharides

This class of polysaccharides contain only 1 type of

monomeric unit. i.e. all the monsaccharide units are
the same. There are two types/classes;
1. Storage homopolysaccharide.
2. Structural homopolysaccharide.
 Storage homopolysaccharides. Eg. Starch &
glycogen
Starch and glycogen are the most important storage
polysaccharides in nature (in plants and animal cells
respectively). They are stored fuels and both occur
intracellularly as large clusters or granules.
Both are heavily hydrated because they have many
exposed hydroxyl groups available to hydrogen bond
with water.
 Starch
It is especially abundant in tubers such as yam, cassava,
potatoes and in seeds such as corn. It contains 2 types of
glucose polymer viz Amylose & Amylopectin. Amylose
consists of long unbranched chains of D-glucose units
linked by (α(1-4) linkages. The chain varies in mol. wt from
a few thousand to 500,000 while Amylopectin has a high
mol. wt of up to 1 million and is highly branched.
Amylopectin has about 1 α-1, 6- linkage in 12-30
α-1, 4- linkages. More than half of the carbohydrates
ingested by human beings is starch. Both amylopectin and
amylose are rapidly hydrolysed by α-amylase, an enzyme
secreted by the salivary glands.
 Glycogen

It is the main storage polysaccharide in animal cells.

Like starch, glycogen is made up of amylose and
amylopectin. The glucose units are linked by α-1, 4-
glycosidic bond and the branches by α-1, 6-glycosidic
bonds.
Branches are found in about 10 glucose units making
glycogen a highly branched molecule and therefore
more compact than starch. Glycogen is abundant in the
liver (where it may constitute 7% of the wet weight)
and skeletal muscle.
 Structural homopolysaccharides. E.g. Cellulose
and Chitin
Cellulose:
It is another polysaccharide of glucose found in plants. It is a
fibrous, tough, water insoluble substance found in the cell
walls of plants, particularly in stalks, stems, trunk and all
the woody portions of plant tissues. It occurs as almost
pure cellulose in cotton.
Cellulose is an unbranched linear polymer of D-glucose
residues joined by β-1,4-glycosidic linkages.
D-glucose units that form cellulose is between 10,000 to
15,000 and it resembles amylose. Th β-configuration allows
cellulose to form very long straight chains.
Contd.
The straight chain formed by β-linkages is
optional for the construction of fibres having a
high tensile strength. Most animals cannot digest
cellulose because they lack cellulase, an enzyme
that hydrolyse the β-1, 4-glycosidic bond. Termites
harbours a symbiotic organism Trichonympha in
their intestinal track which secretes cellulase and
can therefore digest cellulose. i.e. wood.
Wood-rot fungi and bacteria also produces
cellulase.
Contd.
Ruminant animals such as cattle, sheep, goats are
the only vertebrates that can digest cellulose. Their
extra stomach(rumen), contains bacteria that
secretes cellulase.
However, dietary fibres such as cellulose ar still
important in diets by increasing the rate at which
digestion products pass through the large intestine
and reduces exposure to toxins in our diets.
 Chitin

It is a linear structural polysaccharide composed of N-

acetyl-D-glucosamine residues in β-linkages.
The only chmical difference with cellulose is by
replacing the OH group on C-2 of cellulose with an
acetylated amino group.
Chitin is the principal component of the hard
exoskeleton of arthropods. i.e. the insects, lobsters and
crabs.
 Heteropolysaccharide
It contains two or more different kinds of monomeric
units. It provides extracellular support for organisms of
all kingdoms e.g. rigid layer of bacterial cell envelope
(peptidoglycan). The extracellular matrix which
provides protection can account for the high viscosity
and lubricating properties of some extracellular cell
wall.
Bacterial cell wall is made up of heteropolysaccharides
containing alternating N-acetyl glucosamine and N-
acetyl muramic acid. The linear polymer lie side by side
in the cell wall and is cross-linked by short peptides.
The cross linked peptidoglycan is degraded by enzyme
called lysozyme
 Glycosaminoglycams and proteoglycans
These are components of d extracellular matrix which is a
gel-like material that fills the xtracellular space in animal
tissues. They are heteropolysaccharides having an
interlocking meshwork with fibrous proteins.
Glycosaminoglycans are linear polymers composed of
repeating disaccharide units containing either N-acetyl
glucosamine or N-acetyl galactosamine and a uronic acid
usually glucuronic acid.
In some glycosaminoglycans, one or more –OH groups of
the amino sugars is esterified with sulphate (SO42-). The
combination of sulphate group and coo- on uronic acid
gives the high density of –ve charge of
glycosaminoglycans.
Contd.
Glycosaminoglycans, when attached to xtracellular
proteins will form Proteoglycans.
 The major glycosaminoglycans in animals are:
Chondrotin sulphate, Keratan sulphate, Heparin,
Dermatan sulphate, and Hyaluronic acid.
 Proteoglycans were formerly called
mucopolysaccharides and so mucopolysaccharidoses
is a collection of diseases that result from the
inability to degrade glycosaminoglycans.
All mucopolysaccharidoses result in skeletal deformities
and reduced life expectancies.
 Cartilage

The proteoglycan in the extracellular matrix of cartilage is

among the best characterised members of the class of
proteoglycans. The key component of cartilage are
proteoglycan, aggrecan and protein –collagen i.e the major
component of cartilage is agrrecan and collagen. Collagen
provides structure and tensile strength while Aggrecan serves
as a shock absorber. Aggrecan can cushion compressive forces
because it can absorb water which enables it to spring back
after having been deformed e.g. when pressure is exerted as
when the foot hits the ground while walking, water is
squeezed from the glycosaminoglycans cushioning the impact
when the
Contd.
pressure is released, the water rebinds.
Proteolytic degradation of aggrecan and collagen
can result in osteoarthritis.