1: Biochemistry of macromolecules and metabolic pathways

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Carbohydrates
Carbohydrates are a key group of biological molecules about 10% of all the
organic matter of a cell is made up of carbohydrates. This topic guide looks at
their basic chemical structures and functions, as well as carbohydrates in the
environment.
The three carbohydrates of interest that will be covered in this topic guide
are starch, glycogen and cellulose. These are needed as an energy source, an
energy store and as a major structural component in plants, respectively.
On successful completion of this topic you will:
understand the chemical principles that apply to the structures of
biological building block molecules (LO1)
understand the structures of biological macromolecules and the
relationships to biological functions (LO2).
To achieve a Pass in this unit you need to show that you can:
explain the principal properties and classification of monosaccharides,
aldoses and ketoses (1.2)
review the major features of storage and structural polysaccharides (2.3).

1: Biochemistry of macromolecules and metabolic pathways

1 Monosaccharides
Before you start

Key terms
Monosaccharide: A single organic
unit containing carbon, hydrogen
and oxygen.
Disaccharide: Two single
monosaccharide units bonded
together by a glycosidic bond.
Glycosidic bond: A bond formed
between two monosaccharides when
a condensation reaction takes place
to remove water.
Triose: Monosaccharide with three
carbon atoms.
Pentose: Monosaccharide with five
carbon atoms present.
Hexose: Monosaccharide with six
carbon atoms present.
Aldehyde: An organic compound
with the structure RCHO consisting
of a carbon double bond oxygen
bonded to a hydrogen and an R
group.
Aldose: Monosaccharide with an
aldehyde carbonyl group.
Ketone: An organic compound with
the structure RC(=O)R. R and R can
be a variety of carbon-containing
groups. There is a C=O bonded to two
other carbon atoms.
Ketose: Monosaccharide with a
ketone carbonyl group.
O
R

Figure 1.5.1: Chemical structure

of an aldehyde group.

If you need to check your understanding of proteins, carbohydrates, lipids and nucleic acids,
Unit2Module 1 of OCR AS Biology (P. Kennedy and F. Sochacki, 2008), offers a good introduction
tothe topic.
If you need to check your understanding of aerobic respiration and the stages of glycolysis, link
reaction, the Krebs cycle and the electron transport chain, you may find Unit 1 Module 4 of OCR A2
Biology (S. Hocking, 2008) useful.

A carbohydrate is an organic compound that contains carbon, hydrogen

and oxygen. The simplest unit of a carbohydrate is a monosaccharide. If two
monosaccharides join together because of a condensation reaction, it creates a
disaccharide. A water molecule is removed and a new covalent bond is formed
between the two monosaccharides called a glycosidic bond.
Monosaccharides are grouped depending on the number of carbon atoms
theyhave:
three carbon atoms present are classified as triose sugars
five carbon atoms present are classified as pentose sugars
six carbon atoms present are classified as hexose sugars.

Aldoses and ketoses

Monosaccharides with one aldehyde group (CH=O) (see Figure 1.5.1) per
molecule are called aldose sugars. A common example is glucose. The chemical
formula takes the form Cn(H2O)n.
Monosaccharides with one ketone group (see Figure 1.5.2) per molecule are
known as ketose sugars. A common example is fructose found in fruits. The
chemical formula takes the form Cn(H2O)n.
The structures of an aldose and a ketose are shown in Figure 1.5.3.
H

O
R

If you find some parts of this unit challenging, remember you are working at a higher level than
you may be used to. In this unit it is important that you fully understand the following themes and
topics before you begin:
structure and function of biological molecules
enzyme structure and function
aerobic respiration.

H
R

Figure 1.5.2: Chemical structure

of a ketone group.

OH

OH

H
An aldose

OH

OH

H
A ketose

Figure 1.5.3: Structure of

aldose and ketose sugar.

1.5: Carbohydrates

1: Biochemistry of macromolecules and metabolic pathways

Glucose

H
H

C 6 OH
C

H
C4
HO
H

H
OH

1C

OH
C2

C3

OH

Figure 1.5.4: Chemical

structure of a hexose sugar.

Figure 1.5.5: Chemical structure

of -glucose and -glucose.

Glucose (D-glucose, dextrose) is the main source of energy for living organisms.
It is a hexose sugar with the formula C6H12O6. Hexoses form cyclic sugars (see
Figure1.5.4). There are two forms of cyclic sugars, -glucose and -glucose, and
when a ring structure forms, both form in different ways. In -glucose the C1 atom
has an OH group below the ring and in -glucose the OH group is above C1 (see
Figure 1.5.5).
6

CH2OH
5

CH2OH
O
H

H
1

OH

OH
3

H
OH
Alpha-glucose

O
OH

H
1

OH

OH

OH
3

H
OH
Beta-glucose

Reducing sugars
Glucose, fructose and galactose are sometimes referred to as reducing sugars
as they have the ability to reduce other compounds by losing electrons to other
compounds. It is the presence of the aldehyde group in aldose sugars at the
terminal end of the chain structure that enables reduction to occur ketose sugars
would therefore not behave in this way, except fructose because of the position of
the ketone group.
A standard test for the presence of reducing sugars involves heating the sample
with Benedicts solution. The hydrogen (H) group of the aldehyde loses its
electrons to copper II ions (Cu2+) in solution and reduces the copper, while the
hydrogen is oxidised, becoming H+. The double bond breaks and the oxygen
bonds to the copper, producing copper oxide.
Benedicts solution can be used for medical purposes. The presence of a reducing
sugar in urine is an indication of diabetes mellitus; further tests should be carried
out in order to ascertain which sugar is present as it is only glucose that is
indicative of diabetes.

Optical isomerism

X
Y

C
Z

W
Chiral centre

Figure 1.5.6: Structure of a chiral carbon.

Monosaccharides can form optical isomers and can be mirror images of each
other. A chiral carbon, a carbon that has four groups attached (see Figure 1.5.6),
can identify an optically-active organic compound. The attached groups could be
a single H (hydrogen) atom, a functional group or a chain of one or more other
carbons.
Each carbon atom in a monosaccharide, except the first and the last that support
a hydroxyl group, is chiral. This is important because a number of isomeric
forms exist all with the same chemical formula. Galactose and glucose are both
aldohexoses, but have different chemical and physical properties look at
Figure1.5.7 and carefully examine their structures.

1.5: Carbohydrates

1: Biochemistry of macromolecules and metabolic pathways

Figure 1.5.7: Structural difference
between D-glucose and D-galactose.

1 CO

1 CO

H
O
H

3
H

C
4

H C
6

H
H

C H

C H

H O

C H

H
O

C
H C

H
H
O

6
H

C H
O

D-Glucose

C H
O

D-Galactose

Monosaccharides are grouped in the D-family according to the positioning of the

OH group. The OH group should be to the right of the chiral carbon that is the
furthest from the aldehyde group. For example, if the aldehyde is attached to the
C1 carbon atom, the carbon furthest away with an OH group will be the C5 carbon
atom. Both glucose and galactose are part of the D-family because their OH
groups are positioned to the right of C5 carbon atom (see Figure 1.5.7).

2 Polysaccharides
Starch
Starch is a mixture of two different compounds, amylose and amylopectin.
Amylose is a polymer made of glucose monomers joined by -1,4-glycosidic links
that bond on a slight angle, creating a spiral-shaped molecule. This polymer is
unbranched, whereas amylopectin has both an -1,4-glycosidic link and an
-1,6-glycosidic link, and this creates branching. The basic structure of starch is
shown in Figure 1.5.9.
Starch is an important storage chemical in plants; it is compact, insoluble and
readily broken down into glucose to release energy. Amylase is a digestive enzyme
found in saliva and it breaks starch into smaller molecules (see Figure 1.5.8).

1.5: Carbohydrates

1: Biochemistry of macromolecules and metabolic pathways

Figure 1.5.8: Enzymatic
hydrolysis of starch.

CH2OH
H
O

O H
OH H
H

CH2

CH2OH

O H
H
OH H
H

OH

Starch

OH O

CH2OH

O H
H
OH H
H

OH

O H
H
OH H

OH

CH2OH
H
O

O H
OH H
H

OH

Amylase
CH2OH
O OH
OH H
HO
H
H
OH
Glucose
H

Glycogen
Glycogen is structurally similar to amylopectin but with more branches. This is
an advantage for this storage carbohydrate because it provides more ends for
glucose molecules to be added to or removed from for efficient storage. The basic
structure of glycogen is shown in Figure 1.5.9.
We store glycogen in the liver and the muscles so that glycogen is easily accessible
when glucose is needed. Glycogen is easily broken down to glucose when the
bodys glucose supply is depleted.

Cellulose
Cellulose is the most abundant structural polysaccharide in nature; it gives
strength to plant cell walls. Cellulose chains are made from -glucose molecules
arranged in many -1,4-glycosidic links and this produces unbranched chains.
The cellulose molecules are arranged straight next to others and form hydrogen
bonds along the complete length. This produces microfilaments bundled into
microfibrils and, again, into macrofibrils. The basic structure of cellulose is shown
in Figure1.5.9.
Humans are unable to digest cellulose. However, it is necessary to stop problems
like constipation as it provides bulk for peristalsis. Cellulose is a very strong, useful
component that we also use to produce paper and cotton.

1.5: Carbohydrates

1: Biochemistry of macromolecules and metabolic pathways

Figure 1.5.9: Basic structures of
starch, cellulose and glycogen.

Starch
O

Cellulose

O
Glycogen

O
O

Further reading
Take it further
Find out about the polysaccharide
chitin.
1 Draw the structure of chitin.
2 Where is chitin found?
3 Which other element is found in
chitin?
4 Describe the formation of chitin.

Boyle, M. & Senior, K. (2008) Biology, 3rd Edition, HarperCollins

Campbell, M.K. & Farrell, S.O. (2011) Biochemistry, Cengage Learning
Kennedy, P., Sochacki, F. & Hocking, S. (2008) OCR Biology AS, Heinemann (Pearson Education
Limited)
Kennedy, P., Sochacki, F., Winterbottom, M. & Hocking, S. (2008) OCR Biology A2, Heinemann
(Pearson Education Limited)
Moran, L., Horton, R., Scrimgeour, G., Perry, M. & Rawn, D. (2011) Principles of Biochemistry
(International Edition), 5th Edition, Pearson

Acknowledgements
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1.5: Carbohydrates