Lecture 1 (1) SBC 100

Chapter 1
SBC 100: Structures of

Biomolecules
1. Carbohydrates: Life’s
Sweet Molecules
Dr. Arika, Ph.D
1
Chapter Outline
1.1 Classes of Carbohydrates

1.2 Monosaccharides
1.3 Oxidation and Reduction Reactions
1.4 Ring Formation—The Truth about
Monosaccharide Structure
1.5 Disaccharides
1.6 Polysaccharides
1.7 Carbohydrates and Blood
© 2011 Pearson Education, Inc. Chapter 5 2

Introduction to Carbohydrates
• Carbohydrates are compounds of tremendous
biological importance:
– they provide energy through oxidation
– they supply carbon for the synthesis of cell
components
– they serve as a form of stored chemical energy
– they form part of the structures of some cells and
tissues
• Carbohydrates, along with lipids, proteins, nucleic
acids, and other compounds are known as
biomolecules because they are closely associated
with living organisms. Biochemistry is the study of
the chemistry of biomolecules and living organisms.
3
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.
4
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.
5
1.1 Classes of Carbohydrates
A. Monosaccharides
Simple sugars that cannot be hydrolyzed to smaller sugars.
i. Trioses: 3-carbon sugars
e.g., Glyceraldehyde, Dihydroxyacetone
ii. Tetroses: 4-carbon sugars
e.g., Erythrose
iii. Pentoses: 5-carbon sugars
e.g., Ribose, Xylose, Arabinose
iv. Hexoses: 6-carbon sugars
e.g., Glucose, Fructose, Galactose, Mannose
6
1.1 Classes of Carbohydrates, Continued
B. 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.
Examples include:
i. Maltose (Glucose + Glucose)
ii. Sucrose (Glucose + Fructose) - common table
sugar
iii. Lactose (Glucose + Galactose) - milk sugar
iv. Trehalose (Glucose + Glucose) - found in some
fungi and insects
7
C. Oligosaccharides:
•Composed of 3-10 monosaccharide units.
i. Raffinose: A trisaccharide (Galactose +
Glucose + Fructose)
ii. Stachyose: A tetrasaccharide found in
beans

D. Polysaccharides are large molecules
containing 10 or more monosaccharide units.
Carbohydrate units are connected in one
continuous chain or the chain can be branched.
9
• Polysaccharides:
• Complex carbohydrates made up of more than 10
monosaccharide units includes:
i. Starches: Major storage form of energy in plants.
i. Amylose: Linear polymer of glucose
ii. Amylopectin: Branched polymer of glucose
ii. Glycogen: The major storage form of energy in animals, highly branched
polymer of glucose.
iii. Cellulose: Linear polymer of glucose; main component of plant cell walls.
iv. Chitin: Made of N-acetylglucosamine; found in the exoskeleton of
arthropods and cell walls of fungi.
v. Hemicellulose: Found in plant cell walls; comprised of various sugars.
vi. Pectins: Found in plant cell walls; involved in plant growth and fruit
ripening.
10
E. Derived Carbohydrates:
– They are derived from simple carbohydrates through various
reactions.
• Sugar Alcohols: e.g., Sorbitol, Mannitol, Xylitol
• Amino Sugars: e.g., Glucosamine, Galactosamine
• Sugar Acids: e.g., Glucuronic acid, Mannuronic acid
• Sugar Esters: e.g., Sucrose octaacetate
•N/B: Each category of carbohydrate plays a unique role in
biology. For example, while monosaccharides and
disaccharides are often used for immediate energy needs,
polysaccharides like starch and glycogen act as storage
forms of energy. Cellulose and chitin, on the other hand,
serve structural roles in plants and animals, respectively.
11
1.2 Monosaccharides
• 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.
12
1.2 Monosaccharides, Continued
The functional groups of glucose are shown in

the figure below.
13
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).
14
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
• Tertiary (3o) alcohols have three alkyl groups
15
Alcohols
• Monosaccharides contain both primary and
secondary alcohols.
16
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.
17
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.
18
Aldehydes
• Monosaccharides can
contain an aldehyde group
on one end of the molecule
in addition to multiple
hydroxyl groups.
19
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.
20
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.
21
• 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.
22
• 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.
23
24
Aldohexose and ketopentose differ in the number of

carbon atoms and in the type of carbonyl group
they contain.
25
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.
26

• 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?
27
• 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.
28
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.
29
projection: Glyceraldehyde, the simplest carbohydrate, exists in
two isomeric forms that are mirror images of each other:
30

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.

• These forms are stereoisomers of each other.
• Glyceraldehyde is a chiral molecule — it

cannot be superimposed on its mirror image.
• The two mirror image forms of glyceraldehyde
are enantiomers of each other.
32
• Enantiomers are written as if there is a

mirror placed between the two molecules.
• Enantiomers of D- and L-glucose are:
33
34
35
36
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.
• Diastereomers that differ by one chiral center
are called epimers.
37
38
• Carbonyl groups can also react with a hydroxyl
functional group (–OH).
• When this happens, a hemiacetal functional

group is formed as shown:
39
40
Monosaccharide Structure, Continued
A hemiacetal can form within a monosaccharide
since it contains both a carbonyl and several
hydroxyl functional groups.
41
• The carbonyl carbon that reacts to form the
hemiacetal is referred to as the anomeric
carbon.
• Two ring arrangements can be produced. These

are termed anomers, and are referred to as the
alpha () and beta (β) anomer.
• The position of the –OH group on the anomeric

carbon relative to the position of the carbon
outside the ring determines the type of anomer
present.
42
• 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.
43
In Summary
44
• 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.
45
46
• 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.
47
In Summary:
48
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.
49
• Diabetics have difficulty getting glucose in their

cells, which is why they must monitor their blood
glucose levels regularly.
• Glucose is one of the monosaccharides of

sucrose (table sugar) and lactose (milk sugar)
as well as the polysaccharides glycogen, starch,
and cellulose.
50
• 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.
51
• 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.
52
• 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.
53
• 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.
54
55
56
1.5 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.
57
1.5 Oxidation and Reduction Reactions,
Continued
• When copper metal (shiny orange metal) is
exposed to oxygen, an ionic compound,
copper(II) oxide, is produced. This compound is
greenish in color. This reaction is shown as:
• The copper atoms in the reactant lose electrons

to form the Cu2+ ions in the product. The copper
has undergone oxidation.
58
Continued
• The electrons lost by copper atoms are
transferred to the oxygen atom, which then
becomes O2-. Oxygen has undergone reduction.
• While the copper was being oxidized, oxygen

was being reduced.
• Copper then becomes the reducing agent

(causing oxygen to be reduced) and oxygen is
the oxidizing agent (causing copper to be
oxidized).
59
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:
60
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.
61
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.
62
Continued
The product of this reaction, copper(I) oxide
(Cu2O), is not soluble and forms a brick red
precipitate in solution.
63
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.
64
Continued
This rearrangement can be shown as:
65
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.
66
Continued
Reduction of glucose produces the sugar alcohol,
sorbitol, which is an artificial sweetener.
67
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.
68
Course Coordinator: Dr. Arika, Ph.D
•The End
69

Lecture 1 (1) SBC 100

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Chapter 1

SBC 100: Structures of

Dr. Arika, Ph.D

1.1 Classes of Carbohydrates

© 2011 Pearson Education, Inc. Chapter 5 2

• Simple carbohydrates are referred to as

• Consumption of more sugar than is needed for

• Complex carbohydrates include starches and

• Carbohydrates are found on the surface of cells

• ABO blood markers found on red blood cells

• Carbohydrates in our body prevent blood clots.

B. Disaccharides consist of two monosaccharide

© 2011 Pearson Education, Inc. Chapter 5 8

• Monosaccharides contain the elements carbon,

• Monosaccharides contain several functional

The functional groups of glucose are shown in

Functional Groups in Monosaccharides—

• Monosaccharides are classified according to the

• Carbohydrates are further classified on whether

• For example, glucose, the most abundant

• Fructose, known as fruit sugar, contains six

Aldohexose and ketopentose differ in the number of

Multiple chiral centers

Multiple chiral centers

Representing stereoisomers—the Fischer

Representing stereoisomers—the Fischer

© 2011 Pearson Education, Inc. Chapter 5 31

• Glyceraldehyde is a chiral molecule — it

• Enantiomers are written as if there is a

Stereoisomers that are not enantiomers

• When this happens, a hemiacetal functional

• Two ring arrangements can be produced. These

• The position of the –OH group on the anomeric

• In the  anomer, the –OH on the anomeric

• In the β anomer, the –OH on the anomeric

• The ring structure of D-fructose contains four

• In a furanose, carbons 1 and 6 remain outside

• In a five-membered and six-membered ring, the

• In the alpha anomer, the –OH on the anomeric

• In the beta anomer, the –OH on the anomeric

• Glucose is the most abundant monosaccharide

• Glucose is also known as dextrose, blood sugar,

• Glucose is broken down in cells to produce

• Diabetics have difficulty getting glucose in their

• Glucose is one of the monosaccharides of

• Galactose is found combined with glucose in the

• A single chiral center (carbon 4) in galactose is

• Diastereomers that differ by one chiral center

• Mannose, a monosaccharide, is found in some

• Cranberries contain high amounts of mannose,

• Mannose is an epimer of glucose.

• Fructose is combined with glucose to give

• Fructose is the sweetest monosaccharide and is

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

• Pentoses are five-carbon sugars and include

Oxidation and Reduction

• Oxidation and reduction reactions are commonly

• Oxidation is a loss of electrons.

• Reduction is a gain of electrons.

• The mnemonic “OIL RIG” helps remember redox

• The copper atoms in the reactant lose electrons

• While the copper was being oxidized, oxygen

• Copper then becomes the reducing agent