TOPIC-CARBOHYDRATES: LIFE’S

SWEET MOLECULES
PREPARED BY-SHWETA BAKSHI

1
INTRODUCTION TO CARBOHYDRATES
• Carbohydrates are sugars and provide energy when
consumed.

• Our bodies break down carbohydrates to extract

energy. Carbon dioxide and water are released in the
process.

• Glucose is the primary carbohydrate our bodies use to

produce energy.

• Carbohydrates are classified as biomolecules.

2
INTRODUCTION TO CARBOHYDRATES, CONTINUED
• Simple carbohydrates are referred to as simple
sugars and are often sweet to the taste.

• Consumption of more sugar than is needed for energy

results in conversion of these sugars to fat.

• Complex carbohydrates include starches and the plant

and wood fibers known as cellulose.

3
INTRODUCTION TO CARBOHYDRATES, CONTINUED
• Carbohydrates are found on the surface of cells
where they act as “road signs” allowing molecules
to distinguish one cell from another.

• ABO blood markers found on red blood cells are

made up of carbohydrates. They allow us to
distinguish our body’s blood type from a foreign
blood type.

• Carbohydrates in our body prevent blood clots.

They are also found in our genetic material.

4
 CLASSES OF CARBOHYDRATES
• Monosaccharides are the simplest carbohydrates. They
cannot be broken down to smaller carbohydrates.

• Disaccharides consist of two monosaccharide units joined

together; they can be split into two monosaccharides. Sucrose,
table sugar, can be broken down into glucose and fructose.

• Oligosaccharides contain anywhere from three to nine

monosaccharide units. ABO blood groups are oligosaccharides.

5
 CLASSES OF CARBOHYDRATES, CONTINUED
Polysaccharides are large molecules containing 10 or more
monosaccharide units. Carbohydrate units are connected in one
continuous chain or the chain can be branched.

6
 MONOSACCHARIDE
• Monosaccharides contain the elements carbon, hydrogen, and
oxygen, and have the general formula Cn(H2O)n, where n is a
whole number 3 or greater.

• Monosaccharides contain several functional groups. They contain

the hydroxyl group represented as –OH. They also contain a
carbonyl group, which is an oxygen double bonded to a carbon
atom. The carbonyl group may be an aldehyde or a ketone.

7
 MONOSACCHARIDES, CONTINUED
The functional groups of glucose are shown in the figure below.

8
MONOSACCHARIDE, CONTINUED
FUNCTIONAL GROUPS IN MONOSACCHARIDES—ALCOHOLS,
ALDEHYDES, AND KETONES

Alcohols
• Alcohol is an organic compound containing the –OH
group.
• Ethanol is one of the simplest alcohols and is prepared
from the fermentation of simple sugars in grains and fruits.
Ethanol is present in beer and liquors, and is used as an
alternative fuel blend, such as gasohol and E85 (85%
ethanol and 15% gasoline).
9
 MONOSACCHARIDE, CONTINUED
Alcohols
• Alcohols are classified by the number of alkyl groups attached to
the carbon atom containing the hydroxyl group. The number of
alkyl groups impacts the reactivity of the alcohol.
• Primary (1o) alcohols have one alkyl group attached to the
alcoholic carbon.
• Secondary (2o) alcohols have two alkyl groups attached to the
alcoholic carbon.
• Tertiary (3o) alcohols have three alkyl groups attached to the
alcoholic carbon.

10
 MONOSACCHARIDE, CONTINUED
Alcohols
• Monosaccharides contain both primary and secondary alcohols.

11
 MONOSACCHARIDE, CONTINUED
Aldehydes
• An aldehyde is an organic compound containing the carbonyl group.
• Benzaldehyde, a compound responsible for the aroma of
almonds and cherries, is one example.

12
 MONOSACCHARIDES, CONTINUED
Aldehydes
• Members of this family always contain a
carbonyl group with a hydrogen atom
bonded to one side and an alkyl or
aromatic bonded to the other. An
exception is formaldehyde (a
preservative), which has two hydrogens
bonded to the carbonyl group.

13
MONOSACCHARIDES, CONTINUED

Aldehydes
• Monosaccharides can contain an
aldehyde group on one end of the
molecule in addition to multiple
hydroxyl groups.

14
 MONOSACCHARIDES, CONTINUED
Ketones
• A ketone also contains the carbonyl group, but has an alkyl or
aromatic group on both sides of the carbonyl group.
• Acetone is the simplest ketone. It is the main component of
fingernail polish remover.

15
 MONOSACCHARIDES, CONTINUED
Ketones
• A wide variety of biologically important compounds contain a ketone
group.
• Pyruvate is a ketone-containing compound formed during the
breakdown of glucose.
• Butanedione, the flavor of butter, contains two ketone groups.

16
MONOSACCHARIDES, CONTINUED
• Monosaccharides that contain an aldehyde group are
referred to as an aldose. Those that contain a ketone
group are referred to as a ketose.

• Monosaccharides are classified according to the

number of carbon atoms. Most common
monosaccharides have three to six carbon atoms.
– Triose contains three carbons.
– Tetrose contains four carbons.
– Pentose contains five carbons.
– Hexose contains six carbons.
17
 MONOSACCHARIDES, CONTINUED
• Carbohydrates are further classified on whether they contain an
aldehyde or ketone group.

• For example, glucose, the most abundant monosaccharide found

is nature, contains six carbons and an aldehyde group. It is
classified as an aldohexose.

• Fructose, known as fruit sugar, contains six carbons and a ketone

group. It is classified as a ketohexose.

18
 MONOSACCHARIDES, CONTINUED
Aldohexose and ketopentose differ in the number of carbon
atoms and in the type of carbonyl group they contain.

19
 MONOSACCHARIDES, CONTINUED
Stereochemistry in Monosaccharides

Multiple chiral centers

• Recall that a chiral center is a carbon atom that has four different
atoms or groups of atoms attached to it.
• Glucose, a ketohexose, contains four different chiral centers, each
with a tetrahedral geometry.

20
 MONOSACCHARIDES, CONTINUED
Multiple chiral centers
• Carbons 2 through 5 of glucose are
tetrahedral and have four different
atoms or groups of atoms attached.
Carbons 1 and 6 are not chiral centers.
Why?

21
MONOSACCHARIDES, CONTINUED
Multiple chiral centers
• Groups bonded to each chiral center have two different
arrangements or mirror images, which result in
stereoisomers.
• The number of stereoisomers for a molecule increases
with the number of chiral centers in the molecule.
• The general formula for determining the number of
stereoisomers is 2n, where n is the number of chiral
centers present in the molecule.
• Glucose has 4 chiral centers, so there are 16
stereoisomers, 24 = 16.
22
 MONOSACCHARIDES, CONTINUED
Representing stereoisomers—the Fischer projection
• Fischer projection is a simple way of indicating chiral molecules
by showing their three-dimensional structure in two dimensions,
without showing all the wedges and dashes on all the chiral
centers.
• In the Fischer projection, horizontal lines on a chiral center
represent wedges, and vertical lines on a chiral center represent
dashes.

23
 MONOSACCHARIDES, CONTINUED
• Representing stereoisomers—the Fischer
projection
– In the Fischer projection, a chiral carbon is not
shown, but is implied at the intersection of lines.
– Consider the Fischer projection of
glyceraldehyde, the simplest aldose, shown on the
next slide.

24
 MONOSACCHARIDES, CONTINUED
Representing stereoisomers—the Fischer projection

25
MONOSACCHARIDES, CONTINUED
Representing stereoisomers—the Fischer projection
• D and L designations of sugars are based on the Fischer
projection positioning in glyceraldehyde.
• All D-sugars have the –OH on the chiral carbon farthest
from the carbonyl group on the right side of the molecule.
• All L-sugars have the –OH on the chiral carbon farthest
from the carbonyl group on the left side of the molecule.
• Most sugars in nature have the D designation.

26
 MONOSACCHARIDES, CONTINUED
Representing stereoisomers—the Fischer projection
• Enantiomers are written as if there is a mirror placed
between the two molecules.
• Enantiomers of D- and L-glucose are:

27
MONOSACCHARIDES, CONTINUED
Stereoisomers that are not enantiomers
• How are all stereoisomers of D-glucose related since only
one mirror image exists for any stereoisomer?
• Stereoisomers that are not enantiomers are called
diastereomers.
• Diastereomers are stereoisomers that are not exact mirror
images.

28
MONOSACCHARIDES, CONTINUED

29
 MONOSACCHARIDES, CONTINUED
Some Important Monosaccharides

• Glucose is the most abundant monosaccharide found in nature.

• Glucose is also known as dextrose, blood sugar, and grape sugar.

• Glucose is broken down in cells to produce energy.

30
MONOSACCHARIDES, CONTINUED
• Diabetics have difficulty getting glucose in their cells, which
is why they must monitor their blood glucose levels regularly.

• Glucose is one of the monosaccharide of sucrose (table

sugar) and lactose (milk sugar) as well as the
polysaccharides glycogen, starch, and cellulose.

31
MONOSACCHARIDES, CONTINUED
• Galactose is found combined with glucose in the
disaccharide lactose, which is present in milk and other
dairy products.
• A single chiral center (carbon 4) in galactose is
arranged opposite that of glucose, which makes it a
diastereomer of glucose.
• Diastereomers that differ by one chiral center are called
epimers.

32
 MONOSACCHARIDES, CONTINUED
• Mannose, a monosaccharide, is found in some fruits and
vegetables.

• Cranberries contain high amounts of mannose, which has

been shown to be effective in urinary tract infections.

• Mannose is an epimer of glucose.

33
 MONOSACCHARIDES, CONTINUED
• Fructose, a ketose, is commonly referred to as fruit sugar or
levulose.

• Fructose is combined with glucose to give sucrose, or table sugar.

• Fructose is the sweetest monosaccharide and is found in fruits,

vegetables, and honey.

• Fructose is not an epimer of glucose, but it can be broken down

for energy in the body.

34
MONOSACCHARIDES, CONTINUED
• Pentoses are five-carbon sugars and include ribose and 2-
deoxyribose, which are parts of nucleic acids that make up
genetic material.
• Ribonucleic acid (RNA) contains ribose, and
deoxyribonucleic acid (DNA) contains 2-deoxyribose.
• The difference between these two pentoses is the absence
of an oxygen atom on carbon 2 of deoxyribose.
• Ribose is also found in the vitamin riboflavin and other
biologically important molecules.

35
OXIDATION AND REDUCTION REACTIONS
Oxidation and Reduction

• Oxidation and reduction reactions are commonly called

redox reactions.

• Oxidation is a loss of electrons.

• Reduction is a gain of electrons.

• The mnemonic “OIL RIG” helps remember redox

reactions. Oxidation Is Loss, Reduction Is Gain.
36
OXIDATION AND REDUCTION REACTIONS, CONTINUED
• Organic molecules are oxidized if they gain oxygen or lose
hydrogen, and they are reduced if they lose oxygen or gain
hydrogen.

• Some biological reactions undergo oxidation and reduction. A

summary of these characteristics are as follows:

Chapter 5 40
OXIDATION AND REDUCTION REACTIONS, CONTINUED
Monosaccharides and Redox

• An aldehyde functional group can undergo oxidation by

gaining oxygen or it can undergo reduction by gaining
hydrogen.

• During oxidation, aldehydes form carboxylic acids, and

during reduction, they form alcohols.

• In monosaccharides, oxidation produces a sugar acid, and

reduction produces a sugar alcohol.
38
OXIDATION AND REDUCTION REACTIONS, CONTINUED

• Benedict’s test is a useful test to determine the presence of an

oxidation reaction that occurs with sugars.

• Aldose sugars are oxidized by Cu2+ ion, while the Cu2+ ion is
reduced to Cu+ ion.
39
OXIDATION AND REDUCTION REACTIONS, CONTINUED

The product of this reaction, copper(I) oxide (Cu2O), is not soluble

and forms a brick red precipitate in solution.

Chapter 5 43
OXIDATION AND REDUCTION REACTIONS, CONTINUED
• Aldoses are easily oxidized. They serve as reducing agents and
are referred to as reducing sugars.

• Fructose and other ketoses are also reducing sugars, even

though they do not contain an aldehyde group.

• The oxidizing agents can cause a rearrangement of the ketose

to an aldose.

41
OXIDATION AND REDUCTION REACTIONS, CONTINUED

This rearrangement can be shown as:

42
OXIDATION AND REDUCTION REACTIONS, CONTINUED
• Benedict’s test can be used in urine dipsticks to determine the
level of glucose in urine. Excess glucose in urine suggests high
levels of glucose in blood, which is an indicator of diabetes.

• Aldoses or ketoses can be reduced by hydrogen under the

correct conditions, producing sugar alcohols.

• Sugar alcohols are produced commercially as artificial sweeteners

and found in sugar-free foods.

43
OXIDATION AND REDUCTION REACTIONS, CONTINUED

Reduction of glucose produces the sugar alcohol, sorbitol, which is

an artificial sweetener.

44
OXIDATION AND REDUCTION REACTIONS, CONTINUED
• When glucose levels are high in the blood stream, sorbitol can be
produced by an enzyme called aldose reductase.

• High levels of sorbitol can contribute to cataracts, which is a

clouding of the lens in the eye.

• Cataracts are commonly seen in diabetics.

45
RING FORMATION—THE TRUTH ABOUT MONOSACCHARIDE
STRUCTURE, CONTINUED
• In the six-member ring (five carbons and an oxygen) form of D-
isomers, called a pyranose, carbon 6 is always drawn on the top
side of the ring.

• In the  anomer, the –OH on the anomeric carbon is trans to the

carbon outside the ring.

• In the β anomer, the –OH on the anomeric carbon is cis to the

carbon outside the ring.

46
RING FORMATION—THE TRUTH ABOUT MONOSACCHARIDE
STRUCTURE, CONTINUED
• D-Fructose contains both a ketone group and several hydroxyl
groups.

• The ring structure of D-fructose contains four carbons and an

oxygen to form a five-membered ring called a furanose.

• In a furanose, carbons 1 and 6 remain outside the ring.

47
 RING FORMATION—THE TRUTH ABOUT
MONOSACCHARIDE STRUCTURE, CONTINUED
• In a five-membered and six-membered ring, the anomers
are distinguished similarly.

• In the alpha anomer, the –OH on the anomeric carbon is trans

to the carbon outside the ring.

• In the beta anomer, the –OH on the anomeric carbon is cis to

the carbon outside the ring.

48
 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.

49
 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.

50
 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.

51
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.

52
 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.

53
 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.

54
DISACCHARIDES, CONTINUED

55
 DISACCHARIDES, CONTINUED
Three Important Disaccharides—Maltose, Lactose, and Sucrose

The formation of these three common disaccharides is outlined

below.

56
 5.5 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.
57
 DISACCHARIDES, CONTINUED
Maltose, Continued
• The glycosidic bond is α(1→4).

58
 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.

59
DISACCHARIDES, CONTINUED

60
 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  (1→2).
• 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.

61
DISACCHARIDES, CONTINUED

62
 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 -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.

63
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.

64
POLYSACCHARIDES, CONTINUED

Chapter 5 65
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. 66
 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.

67
POLYSACCHARIDES, CONTINUED

Chapter 5 68
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.

69
 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.

70
POLYSACCHARIDES, CONTINUED

Chapter 5 71
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.

72
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.
73
POLYSACCHARIDES, CONTINUED

74
MUCOPOLYSACCHARIDES

Chapter 5 75
Acidic Non Sulfated MPS:
Hyaluronic Acid
Acidic Sulfated MPS:
Heparin
Heparan Sulfate
Chondritin Sulfate
Dermatan Sulfate
Keratan Sulfate
Neutral MPS:
Blood Group Substances
Chapter 5 77
Hyaluronic acid
Hyaluronic acid is present as ground
substance/cementing substance in extra cellular
spaces of connective tissue.
Hylauronidase present in head of sperm ,
hydrolyzes the Hyaluronic acid present on ovum
which facilitates its penetration and fertilization.
Snake venom is rich in Hyaluronidase, thus
snake bite hydrolyzes and liquifies the Hyaluronic
acid present in extracellular spaces of cells
(TOXIN )
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.

79
 Occurrence and Functions Of Heparan
Sulfate

Heparan Sulfate present on

extracellular cell surfaces or
plasma membranes and serves
as receptors
Participate in cell growth, cell
adhesion, and cell -cell
communication.
Occurrence and Functions Of Chondritin
Sulfate

Chondritin Sulfate is present in

connective tissues-bones,
cartilage, tendons .
It gives mechanical strength,
compressibility and support to
connective tissues.
Occurrence and Functions Of Dermatan
Sulfate

Dermatan sulfate especially present in

skin, blood vessels and heart valves
gives mechanical strength and structural
support to these tissues.

Dermatan sulfate plays structural role in

sclera of eye.
Keratan sulfate present in cartilage,
aorta walls, gives structural supports
and mechanical strength.

Keratan sulfate present in cornea

and lens of eye has role in lens
transparency and shape of eye.
Chapter 5 84
Chapter 5 85
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.

86
 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.

Chapter 5 87
 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.

88
THANK YOU