Class: 3rd/ 1st-semester Lec: 3

Dr.: Nabaa Mohsin Kareem

Carbohydrates II
 Carbohydrates are one of the most important classes of biomolecules along
with proteins, and lipids.
 chemical formula CnH2nOn
 Monosaccharides are linked together by glycosidic bonds to form di, oligo-
and a huge variety of polysaccharides
 Carbohydrates are aldehyde (CHO) or ketone (C=O) compounds with
multiple hydroxyl groups (Carbon-oxygen double bonds make the sugars
reactive).

Monosaccharides
Aldehydes or ketones
- Colorless, crystalline solids that are freely soluble in water but insoluble in
nonpolar solvents.
- They are important molecules as well as building units for carbohydrate
- The smallest monosaccharides are:
D and L isomerism
Isomers are molecules with the same kinds and numbers of atoms joined up in
different ways. A carbon atom that contains four different chemical groups forms
an asymmetric (or chiral) center. The prefixes D and L designate the absolute
configuration of the asymmetric carbon farthest from the aldehyde or keto group.
When the OH group on this carbon is on the right, the sugar is the D-isomer; when
it is on the left, it is the L-isomer.
Glyceraldehyde has a single asymmetric carbon and, thus, there are two
stereoisomers of this sugar. D-Glyceraldehyde and L-glyceraldehyde are mirror
images of each other (enantiomers).

Stereoisomer & Epimers:

Stereoisomers have the same chemical formula but differ in the position of the
hydroxyl group on one or more of their asymmetric carbons. Epimers are
stereoisomers that differ in the position of the hydroxyl group at only one of their
asymmetric carbons. D-glucose and D-galactose are epimers of each other,
differing only at C4. D-mannose and D-glucose are also epimers of each other,
differing only at C2.
Glycosidic bond
Glycosidic bonds form through a dehydration reaction and have water as a
byproduct. In this reaction, an alcohol oxygen from one sugar attacks the anomeric
carbon of a neighboring sugar. The hydroxyl group on the anomeric carbon serves
as a good leaving group and forms the –OH component of the water molecule that
will be formed in the reaction. The second hydrogen is removed from the incoming
alcohol, resulting in the formation of the glycosidic bond. Glycosidic bond
formation does NOT happen spontaneously. It requires the action of an enzyme
(not shown in the below diagram).

The naming of Glycosidic bond:

 Glycosidic bonds between sugars are named according to:
1. The numbers of the connected carbons
2. The position of the anomeric hydroxyl group of the sugar.
 If the anomeric hydroxyl group is in α configuration the link is α‐ bond and
if it’s in β, the link is β‐ bond.
Disaccharides:
Two monosaccharides are connected by a glycosidic bond. Disaccharide, also
called double sugar, any substance that is composed of two molecules of simple
sugars (monosaccharides) linked to each other.
Disaccharides are crystalline water-soluble compounds. The monosaccharides
within them are linked by a glycosidic bond (or glycosidic linkage), the position of
which may be designated α- or β- or a combination of the two (α-,β-). Glycosidic
bonds are cleaved by enzymes known as glycosidases. The three major
disaccharides are sucrose, lactose, and maltose.
More specifically, a disaccharide results when two monosaccharides are joined in a
chemical process called dehydration synthesis, which causes two monosaccharides
to combine, losing a water molecule in the process. This process is also known as a
condensation reaction.
• Disaccharides can be named by the organization and linkage or a common name.
Three Important Disaccharides—Maltose, Lactose, and Sucrose
The formation of these three common disaccharides are:

Maltose (Malt Sugar)

Maltose is known as malt sugar.
• The glycosidic bond is α(1→4).
•It is occurring in the Free State in nature, is produced in large quantities by the
hydrolysis of starch during the germination of barley and other grains. so formed
by the breakdown of starch by the action of the enzyme α-amylase.
• One of the anomeric carbons is free, so maltose is a reducing sugar.

Lactose (Milk Sugar)

• The glycosidic bond is  (1→4). 
• One of the anomeric carbons is free, so lactose is a reducing sugar.

 Enzyme lactase hydrolyses lactose to glucose and galactose.

Sucrose (table sugar, can sugar)

 Sucrose, which is formed following photosynthesis in green plants, consists

of one molecule of glucose and one of fructose bonded via an α-,β-linkage.
 Sucrose is not a reducing sugar.
Fermentation:
 Sucrose and maltose will ferment when yeast is added because yeast contains the
enzyme sucrase and maltase.
 Lactose will not ferment because yeast does not contain lactase.

Oligosaccharides:
Oligosaccharides are compound sugars that yield 3 to 10 molecules of the same or
different monosaccharides on hydrolysis.
Polysaccharides
Polysaccharides contain more than 10 monosaccharide units and can be more of
sugar units in length. They yield more than 10 molecules of monosaccharides on
hydrolysis.
Polysaccharides differ from each other in the identity of their recurring
monosaccharide units, in the length of their chains, in the types of bond-linking
units, and in the degree of branching.
They are primarily concerned with two important functions i.e. Structural functions
and the storage of energy.

 High molecular weight

 Only sparingly soluble in water.
 Not sweetish and do not exhibit any of the properties of aldehyde or ketone
group (glycosidic bond).
Polysaccharides are of two types
i. Homopolysaccharides (homoglycans):
•When a polysaccharide is made up of several units of one and the same type of
monosaccharide unit called homopolysaccharide.
• The most common homoglycans are:
1. Starch (glucose only)
2. Dextrins 3. Glycogen
4. Inulin (fructose only) 5. Cellulose (D-glucose only)
ii. Heteropolysaccharides (heteroglycans):
They contain two or more different types of monosaccharide units or their
derivatives.
1. Heparin 2. Agar
3. Hyaluronic acid 4. Gums
5. Blood group polysaccharides.