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
