CARBOHYDRATE CHEMISTRY

Dr. Mohammed Shakil Akhtar

 Lecture Outlines
 Introduction and General Characteristics.
 Function of Carbohydrates.
 Classification of Carbohydrates.
 Properties of Monosaccharides.
 Sterioisomerism
 Optical Activity
 Cyclic Structures
 Anomers and anomeric
carbon  Reducing Sugars
 Glycosides
 Disaccharides
 Polysaccharides
 Glycoproteins
 Sugar
Derivatives
 Introduction and General Characteristics
 Carbohydrates are the single most abundant class
of organic molecules found in nature, constituting
one of the four major classes of biomolecules.

 They are ‘hydrates of carbon’ having the general

molecular formula name (CH2O)n where n= number of
carbon atoms ( 3 or more). They are composed of C, H
and O.
 Most carbohydrates are found naturally in bound
form rather than as simple sugars e.g starch,
glycoproteins and glycolipids.

 Carbohydrates are ‘aldehyde’ or ‘ketone’

compounds with multiple hydroxyl (- OH ) groups.
 When the functional group is
an ‘aldehyde group’ 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 aldehyde or ketone group of a carbohydrate is

also known as a ‘carbonyl group’ and the the carbon
atom of the aldehyde or ketone group is known as the
‘carbonyl carbon’.
ALDOSES
KETOSES
 Definition
Carbohydrates are defined as organic
polyhydroxyaldehyde or polyhydroxyketone or the
compounds which produce them on hydrolysis.
 Functions of Carbohydrates
 Carbohydrates serve as energy stores and fuels.
Breakdown of carbohydrates provides the energy that
maintains life. Glucose is main source of energy for
the brain.
 Carbohydrates participate in the structure of cell
membranes (glycoproteins and glycolipids).
 Pentose sugars (ribose and deoxyribose) form the
structure of nucleic acids.
 Carbohydrates play important roles in recognition
between cell types. Recognition events are important
in normal cell growth, fertilization and transformation
of cells.
 Carbohydrates act as intermediates in the biosynthesis
fats and proteins.
 CLASSIFICATION OF CARBOHYDRATES

They are classified according to the “number of

structural units” into:

 Monosaccharides
 Disaccharides
 Oligosaccharides and
 Polysaccharides
 Monosaccharides
 Monosaccharides are the carbohydrates that cannot
be hydrolysed into simpler units (have one structural
unit). Also known as simple sugars.

 The smallest and the simplest 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 (3C), tetroses(4C),
pentoses(5C), hexoses(6C), heptoses(7C) or
octoses(8C).
2. Type of functional group as aldosugars and
ketosugars.
 Examples of aldoses are glyceraldehyde, erythrose,
ribose, glucose.
 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 Monosaccharide
1. Monosaccharides are crystals and dissolve in water.
2. Monosaccharides 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

Asymmetric Carbon
No Asymmetric 4 Asymmetric 3 Asymmetric
Carbon Carbon Carbon
 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 monosaccharide containing one or 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 that are mirror

images of each other by differing in the configuration
around the asymmetric carbons. They are designated
as “D” and “L” isomers based on the position of –OH
group before the last ( sub-terminal) carbon.
 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 D-sugars”.