Structure of monosaccharide

• Fisher • Haworth • X-ray

projection projection diffraction
• The straight • Cyclic formula analysis
chain structural or ring • Boat and chair
formula structure form
 Straight chain

Ring structure

Chair form
 Isomerism
• The compounds possessing identical molecular
formula but different structures are called
isomers.
Various types of isomerism
1. Structural isomerism
2. Stereoisomerism
 Structural isomerism
• Same molecular formulae but differ from each
other by having different structures.
 Stereoisomerism
• Same molecular formula and same structure
but they differ in configuration.

• That is arrangement of their atoms in space.

• Presence of asymmetric carbon atoms allow

the formation of stereoisomerism
 Stereoisomerism
• The important types of stereoisomerism
associated with glucose are

D and L isomerism
Optical isomerism
Epimerism
α and βanomerism
D and L isomerism
 Optical isomerism
• Optical activity is the capacity of a substance to
rotate the plane polarized light passing
through it.

Clockwise direction
• Dextrorotatory(d) or (+)

Counterclockwise direction
• Levorotatory(l)or (-)
 Optical isomerism

Chiral compounds rotate polarized light clockwise

or counter clockwise through certain angle
 Epimerism

• Epimerism is the stereoisomerism if two

monosaccharides differ from each other in
their configuration around a single specific
carbon(other than anomeric) atom.
Epimerism
 Anomerism
• These are isomers obtained from the change of
position of hydroxyl group attached to the
anomeric carbon e.g. a and b glucose are 2
anomers.
• Also a and b fructose are 2 anomers.
Anomerism
 Mutarotaion
• Mutarotaion is defined as the change in the
specific optical rotation by the interconversion
of α and β forms of D glucose to an
equilibrium mixture
 Structure of oligosaccharides
• Disaccharides

Disaccharides

Reducing Nonreducing

Maltose
Lactose Sucrose
Isomaltose
 DISACCHARIDES

• These are glycosides formed by the condensation of 2

simple sugars.

• If the glycosidic linkage involves the carbonyl groups of

both sugars (as in sucrose) the resulting disaccharide is
non-reducing.

• On the other hand, if the glycosidic linkage involves the

carbonyl group of only one of the 2 sugars (as in maltose
and lactose) the resulting disaccharide is reducing.
 POLYSACCHARIDES

• These are formed by the condensation of n molecules of

monosaccharides with the removal of n-1 molecules of
water. Since condensation involves the carbonyl groups of
the sugars, leaving only one free carbonyl group at the end
of a big molecule, polysaccharides are non-reducing.

• They are of 2 types:

1. Homopolysaccharides (e.g. Starch, Glycogen, cellulose).

2. Heteropolysaccharides (e.g. glycosaminoglycans, glycoproteins)

 a-1,6 linkage between
two glucose units

a- 1,4 linkage between

two glucose units
The ability to digest cellulose
is found only in microorganisms
that contain the enzyme
Cellulase.
Certain animal species (e.g. Cow)
utilize such organisms in their
digestive tracts to digest cellulose
 Monosaccharides
Can be classified as

Aldoses Ketoses Isomers Epimers Enantiomers

if they contain if they contain if they contain if they if they are
Aldehyde Keto Same Differ in Mirror images of
group group chemical configuration each other
H-C=O C=O formula around one
specific carbon
atom
can link to form

Disaccharides Oligosaccharides Polysaccharides

e.g., can be
sucrose = glucose + fructose
Lactose = galactose + glucose
Maltose = glucose + glucose
Homo- Hetero-
e.g., e.g.,
Starch, glycogen, GAGs
cellulose