Lecture 2

2. Carbohydrates:
Disaccharides,
Oligosaccharides &
Polysaccharides
Dr. Arika, Ph.D

1
 Chapter Outline

2.0 Disaccharides
2.1 Oligosaccharides
2.2 Polysaccharides
2.3 Carbohydrates and Blood

2
 2.0 Disaccharides

Condensation and Hydrolysis—Forming and

Breaking Glycosidic Bonds

• The –OH group that is most reactive in a

monosaccharide is the one on the anomeric carbon.

• When this hydroxyl group reacts with another hydroxyl

group on another monosaccharide a glycosidic bond
is formed.

3
 2.0 Disaccharides, Continued

Formation of glycosides is an example of

another type of organic reaction. During this
reaction, a molecule of water is eliminated as
two molecules join.

4
 2.0 Disaccharides, Continued

• Condensation reaction is a type of reaction

that occurs when two molecules are joined and a
water molecule is produced. This type of
reaction is referred to as a dehydration
reaction.

• Hydrolysis reaction is the reverse of a

condensation reaction. A larger molecule forms
two smaller molecules and water is consumed
as a reactant.

5
 2.0 Disaccharides, Continued

Condensation reactions occur between different

types of functional groups that contain an –H in
a polar bond, like O–H or N–H, and an –OH
group that can be removed to form water.

6
 2.0 Disaccharides, Continued

Naming Glycosidic Bonds

• In the slide showing the formation of maltose, we

observed that the glycosidic bond was in the
alpha position. If that bond had been in the beta
position, a different molecule would have been
formed with a different three-dimensional
structure.

• In naming glycosidic bonds, it is necessary to

name the configuration as well as the carbons
involved in the bond formation.
7
 2.0 Disaccharides, Continued

• In the case of maltose, the glycosidic bond is

specified as α(1→4) and is simply stated as
alpha-one-four.

• If the –OH group had been in the beta

configuration when the glycosidic bond was
formed, the bond would be in the β(1→4)
configuration. The molecule formed would be
named cellobiose and would have a different
two-dimensional and three-dimensional shape
than maltose.

8
2.0 Disaccharides, Continued

9
 2.0 Disaccharides, Continued

Three Important Disaccharides—Maltose,

Lactose, and Sucrose

The formation of these three common

disaccharides is outlined below.

10
 2.0 Disaccharides, Continued

Maltose
• Maltose is known as malt sugar.
• It is formed by the breakdown of starch.
• Malted barley, a key ingredient in beer,
contains high levels of maltose.
• During germination of barley seeds, the starch
goes through hydrolysis to form maltose. This
process is halted by drying and roasting
barley seeds prior to their germination.
• One of the anomeric carbons is free, so
maltose is a reducing sugar.
11
 2.0 Disaccharides, Continued

Maltose, Continued
• The glycosidic bond is α(1→4).

12
 2.0 Disaccharides, Continued

Lactose
• Lactose is known as milk sugar.
• It is found in milk and milk products.
• An intolerance to lactose can occur in
people who inherit or lose the ability to
produce the enzyme lactase that hydrolyzes
lactose into its monosaccharide units.
• The glycosidic bond is (1→4).
• One of the anomeric carbons is free, so
lactose is a reducing sugar.

13
2.0 Disaccharides, Continued

14
 2.0 Disaccharides, Continued

Sucrose
• Sucrose is known as table sugar.
• It is the most abundant disaccharide found in
nature.
• Sucrose is found in sugar cane and sugar
beets.
• The glycosidic bond is α1→2 glycosidic
linkage.
• Both anomeric carbons of the
monosaccharides in sucrose are bonded,
therefore, sucrose is not a reducing sugar. It
will not react with Benedict’s reagent. 15
2.0 Disaccharides, Continued

16
2.0 Sucrose

17
2.1 Oligosaccharides

18
 2.3 Polysaccharides
Polysaccharides

Polysaccharides are large molecules of

monosaccharides that are connected to each
other through their anomeric carbons. There are
two types of polysaccharides:

1. Storage polysaccharides contain only α-glucose

units. Three important ones are starch, glycogen,
and amylopectin.

2. Structural polysaccharides contain only -glucose

units. Two important ones are cellulose and chitin.
Chitin contains a modified -glucose unit.
19
 2.3 Polysaccharides, Continued

Storage and structural polysaccharides are made

up of glucose units, but they are structurally and
functionally different because of their glycosidic
bonds and difference in branching.

20
2.3 Polysaccharides, Continued

21
 2.3 Polysaccharides, Continued
Storage Polysaccharides

Amylose and amylopectin—starch

• Starch is a mixture of amylose and amylopectin
and is found in plant foods.
• Amylose makes up 20% of plant starch and is
made up of 250–4000 D-glucose units bonded
α(1→4) in a continuous chain.
• Long chains of amylose tend to coil.
• Amylopectin makes up 80% of plant starch and
is made up of D-glucose units connected by
α(1→4) glycosidic bonds.
22
 2.3 Polysaccharides, Continued

Amylose and amylopectin—starch

• About every 25 glucose units of amylopectin, a
branch of glucose units are connected to the
glucose by an α(1→6) glycosidic bond.
• During fruit ripening, starch undergoes
hydrolysis of the α(1→4) bonds to produce
glucose and maltose, which are sweet.
• When we consume starch, our digestive system
breaks it down into glucose units for use by our
bodies.

23
2.3 Polysaccharides, Continued

24
2.3 Polysaccharides, Continued

25
 2.3 Polysaccharides, Continued

Glycogen
• Glycogen is a storage polysaccharide found in
animals.
• Glycogen is stored in the liver and muscles.
• Its structure is identical to amylopectin, except
that α(1→6) branching occurs about every
12 glucose units.
• When glucose is needed, glycogen is
hydrolyzed in the liver to glucose.

26
 2.3 Polysaccharides, Continued

Structural Polysaccharides

Cellulose
• Cellulose contains glucose units bonded
(1→4).
• This glycosidic bond configuration changes the
three-dimensional shape of cellulose compared
with that of amylose.
• The chain of glucose units is straight. This
allows chains to align next to each other to form
a strong rigid structure.
27
2.3 Polysaccharides, Continued

28
2.3 Cellulose

29
 2.3 Polysaccharides, Continued

Cellulose
• Cellulose is an insoluble fiber in our diet
because we lack the enzyme cellulase to
hydrolyze the (1→4) glycosidic bond.
• Whole grains are a good source of cellulose.
• Cellulose is important in our diet because it
assists with digestive movement in the small and
large intestine.
• Some animals and insects can digest cellulose
because they contain bacteria that produce
cellulase.
30
 2.3 Polysaccharides, Continued

Chitin
• Chitin makes up the exoskeleton of insects and
crustaceans and cell walls of some fungi.
• It is made up of N-acetylglucosamine containing
(1→4) glycosidic bonds.
• It is structurally strong.
• Chitin is used as surgical thread that
biodegrades as a wound heals.
• It serves as a protection from water in insects.
• Chitin is also used to waterproof paper, and in
cosmetics and lotions to retain moisture.
31
2.3 Polysaccharides, Continued

32
 2.4 Carbohydrates and Blood

ABO Blood Types

• ABO blood types refer to carbohydrates on red

blood cells.

• These chemical markers are oligosaccharides that

contain either three or four sugar units.

• Sugar units are D-galactose, L-fucose,

N-acetylglucosamine, and N-acetylgalactosamine.

33
 2.4 Carbohydrates and Blood, Continued

The following shows the carbohydrates and their

attachments in type O, type A, and type B blood.
Type AB blood has both type A and type B sets on
their blood cells.

34
 2.4 Carbohydrates and Blood, Continued

• Type O blood is considered the universal donor

while type AB blood is considered the universal
acceptor.
• The following table shows the compatibility of
blood groups.

35
 2.4 Carbohydrates and Blood, Continued

Heparin

• Heparin is a medically important polysaccharide

because it prevents clotting in the bloodstream.
• It is a highly ionic polysaccharide of repeating
disaccharide units of an oxidized
monosaccharide and D-glucosamine. Heparin
also contains sulfate groups that are negatively
charged.
• It belongs to a group of polysaccharides called
glycosaminoglycans.
36
2.4 Carbohydrates and Blood, Continued

37
 Chapter Summary

1.1 Classes of Carbohydrates

Carbohydrates are classified as monosaccharides

(simple sugars), disaccharides (two
monosaccharide units), oligosaccharides (three to
nine monosaccharide units), and polysaccharides
(many monosaccharide units).

38
 Chapter Summary, Continued

1.2 Monosaccharides

• A monosaccharide has a molecular formula of

Cn(H2O)n, where n = 3–6.

• Fischer projections that highlight chiral centers

are used to represent monosaccharides.

• Most monosaccharides in nature are D-isomers.

39
 Chapter Summary, Continued

1.2 Monosaccharides, Continued

• Multiple chiral centers lead to enantiomers or

diastereomers.

• Important monosaccharides are glucose,

galactose, fructose, mannose, ribose, and
deoxyribose.

40
 Chapter Summary, Continued

1.3 Oxidation and Reduction Reactions

• Oxidation is a loss of electrons and reduction

is a gain of electrons.

• These are common types of reactions in organic

molecules.

• For organic molecules, oxidation is the addition

of oxygen and reduction is the addition of
hydrogen.
41
 Chapter Summary, Continued

1.3 Oxidation and Reduction Reactions,

Continued

• The anomeric carbon of carbohydrates is highly

reactive and can be oxidized to a carboxylic acid
or reduced to an alcohol.

• Monosaccharides are considered reducing

sugars because their anomeric carbon can react.

42
 Chapter Summary, Continued

1.4 Ring Formation—The Truth about

Monosaccharide Structure

• A hydroxyl group and the carbonyl group can

react to enclose the hydroxyl’s oxygen in a ring.

• Because the carbonyl group is planar, two

possible ring arrangements about the anomeric
carbon occur when the ring forms. These are
termed the α and  anomers.

43
 Chapter Summary, Continued

2.1 Disaccharides

• Condensation and hydrolysis are common

reactions that occur in biomolecules.

• Condensation reactions produce a water

molecule while bonding two molecules together.

• Hydrolysis reactions consume a molecule of

water while a molecule is broken into two
smaller molecules.
44
 Chapter Summary, Continued

2.1 Disaccharides, Continued

• Carbohydrates form glycosides when an

anomeric carbon reacts with a hydroxyl group on
a second molecule. The bond formed is called a
glycosidic bond.

• Glycosidic bonds are named by designating the

anomer of the reacting monosaccharide and the
carbons that are bonded, for example, α(1→4).

45
 Chapter Summary, Continued

3.1 Polysaccharides

• A polysaccharide consists of many

monosaccharide units bonded together through
glycosidic bonds.

• Glucose is stored as glycogen in animals and

starch in plants.

• Starch consists of amylose, a linear chain of

glucose, and amylopectin, a branched chain of
glucose.
46
 Chapter Summary, Continued

3.1 Polysaccharides, Continued

• Glycogen contains many more branches in its

structure than amylopectin.

• Two important polysaccharides are cellulose in

plants and chitin in arthropods and fungi.

• Cellulose consists of (1→4) and is the

structural component of plants. It has a linear
structure.
47
 Chapter Summary, Continued

3.1 Polysaccharides, Continued

• Chitin is linear. It contains N-acetylglucosamine.

• Cellulose and chitin form strong, water-resistant

materials when the linear chains are aligned to
each other.

48
 Chapter Summary, Continued

3.3 Carbohydrates and Blood

• The ABO blood groups are oligosaccharides

on the surface of red blood cells.

• The O blood group is considered the universal

donor.

• Heparin, a polysaccharide, functions in the

blood as an anticoagulant and is found as a
coating on medical tubing and syringes during
blood transfusions.
49
Course Coordinator: Dr. Arika, Ph.D

Thank You!

50