CARBOHYDRATE CHEMISTRY

INTRODUCTION
Carbohydrates are the single most abundant
class of organic molecules found in nature,
constituting one of the four major classes of
biomolecules. The other three are proteins, nucleic
acids and lipids.
Carbohydrates are aldehyde or ketone
compounds with multiple hydroxyl groups. The
name carbohydrate arises from the basic molecular
formula (C.H2O)n which shows that these
substances are hydrates of carbon, where n=
number of carbon atoms ( 3 or more).
When the functional group is an aldehyde they
are known as aldoses e.g.glyceraldehyde,
glucose.
When the functional group is a keto group they
are referred to as ketoses e.g. dihydroxyacetone,
fructose

The simplest aldosugar ( aldose) is

glyceraldehyde and the simplest ketosugar
(ketose) is dihydroxyacetone.
ALDOSES

KETOSES

Definition

Carbohydrates are defined as organic

polyhydroxyaldehydes or polyhydroxyketones or
compounds which produce them on hydrolysis.
Functions of carbohydrates
They are important due to their multiple roles in
all forms of life:
They serve as energy stores and fuels. Energy
from the sun captured by plants during
photosynthesis is stored in the form of
carbohydrates. Breakdown of carbohydrates
provides the energy that maintains animal life.
Glucose is main source of energy for the brain.
They participate in the structure of cell
membranes.
Pentose sugars (ribose and deoxyribose) form the
structure of nucleic acids.
Carbohydrates play important roles in recognition
between cell types or recognition of cellular
structures by other molecules. Recognition events
are important in normal cell growth, fertilization
and transformation of cells.
Carbohydrates form the structure of
glycoproteins and glycolipids.
CLASSIFICATION OF CARBOHYDRATES
They are classified according to the number of
structural units into:
Monosaccharides
Disaccharides
Oligosaccharides and
Polysaccharides
Monosaccharides
They are carbohydrates that cannot be
hydrolysed into simpler units.
General formula is (C.H2O)n.

 The smallest ones, for which n = 3, are

glyceraldehyde and dihydroxyacetone. They are
trioses.
Glyceraldehyde is also an aldose because it
contains an aldehyde group; whereas
dihydroxyacetone is a ketose because it contains a
keto group, (the suffix- ose means sugar)
Classification of Monosaccharides
They are classified according to :
1. Number of carbon atoms in the molecule: They
may be subdivided into, trioses, tetroses, pentoses,
hexoses, heptoses or octoses.

2. Type of functional group as aldosugars and

ketosugars.
Examples of aldoses are glyceraldehyde,
erythrose, ribose, glucose and galactose.
Examples of ketoses are dihydroxyacetone,
Erythrulose, Ribulose, Fructose.

DIASACCHARIDES
These carbohydrates yield two molecules of
monosaccharides when hydrolysed.
MALTOSE
GLUCOSE + GLUCOSE
SUCROSE
GLUCOSE + FRUCTOSE
LACTOSE
GLUCOSE + GALACTOSE
OLIGOSACCHARIDES
They yield three to ten molecules of
monosaccharides on hydrolysis, example is
Maltotriose which is a trisaccharide containing
three glucose residues.
POLYSACCHARIDES
They yield more than ten molecules of
monosaccharides on hydrolysis. They may be
either linear or branched polymers and may
contain hundreds or even thousands of
monosaccharide units . Examples are starch,
glycogen, dextran.
Properties of Monosaccharides In Reference to
Glucose

1. All monosaccharide are crystals and dissolve in

water.
2. All have a Sweet taste.
3. Monosaccharides contain asymmetric carbon
atom (which is a carbon atom attached to four
different chemical groups) except
dihydroxyacetone.
Due to presence of asymmetric carbon atom,
monosaccharides have two main physical
properties which are:
Optical Isomerism or Stereoisomerism
Optical Activity
4. Cyclic structure of Monosaccharides
5. Mutarotation
Asymmetric Carbon

No Asymmetric Carbon 4
Optical Isomerism or Stereoisomerism
Optical isomerism or stereoisomerism is the
ability of substances to be present in more than
one form. It is due to the presence of asymmetric
carbon atom. These forms are named optical
isomers.
So optical isomers or stereoisomers or isomers
are compounds that have same structural formula
but differ in their configuration around the
asymmetric carbon atom.
A substance containing more than one
asymmetric carbon atom can exist in a number of
isomers equal to 2n, where n equal to the number
of asymmetric carbon atoms e.g Glucose has 4

asymmetric carbon atoms, so the number of

optical isomers equal to 24 =2x2x2x2 = 16.
ENANTIOMERS
Enantiomers are a type of isomers designated as
D and L isomers that are mirror images of each
other and differ in the configuration around the
asymmetric carbon before the last ( sub-terminal)
e.g D and L glyceradehyde, D and L glucose.

In D isomer (D-glucose) the OH group attached to

the
asymmetric carbon ( sub-terminal C5 )is towards
the
right while in L isomer ( L-glucose) OH group is on
the left.

The majority of the sugars in humans are Dsugars.

EPIMERS
Epimers are sterioisomers that differ in the
position of
(OH) group at only one of their asymmetric carbon
atom
other than before the last ( sub-terminal) carbon
atom. e.g
D-Glucose and D-Galactose are C4 epimers.
D-Glucose and D-Mannose are C2 epimers.
OPTICAL ACTIVITY

It is the ability of an organic compound

containing one or more asymmetric carbon atom to
rotate a beam of polarized light either to the right
or to the left.
If the rotation is to the right it is called
dextrorotatory (+ or d) and if it is to the left it is
known as levorotatory ( - or l ).
Polarized light is the light which vibrates in only
one direction. It is obtained by the passage of
ordinary light through a prism.