Topic 02
Carbohydrates
Unit 1:
Biological Molecules
Introduction
You will no doubt have heard of the term
carbohydrates before, most likely in a dietary
context, found in rice, pasta, pulses, potatoes,
and bread. They are an integral part of a balanced
diet, not just for humans and other mammals but
they are vital in the construction of plants.
In this topic we will find out just why they are
such an important biological molecule, the forms
they take and the structural properties that lend
them to their functions.
Objectives
When you have completed this topic, you should be able to:
Explain how carbohydrates are formed from their
monomers, monosaccharides.
Identify examples of monosaccharides including glucose,
galactose, and fructose
Describe how condensation reactions create glycosidic
bonds that join monosaccharides
Outline the structures of disaccharides and
polysaccharides and the monosaccharides that form them
Describe the use of chemical tests for sugars and starch
Introduction to
Carbohydrates
The carbohydrates are a group of compounds that are
fundamental to all life on earth.
Consisting primarily of carbon and hydrogen they are crucial to many
natural products and to many structures and tissues of cells and organisms.
The carbon is the crucial element here as it possess rather unique quality, in
that it can readily form bonds with other atoms, particularly other carbons,
allowing for long chains of carbon to be created, upon which other carbons
can branch and other atoms and groups of atoms can attach.
Figure 1 demonstrates this, and you can see a “backbone” of six carbons
running through the centre of this glucose molecule:
Glucose
Figure 1 – the formation of the carbon backbone
is evident in the glucose molecule
Carbohydrates get
their name from the
Did you constituent atoms;
carbon (carbo-) and
know? hydrogen (-hydrate)
Monosaccharides
Glucose, as shown in figure 1, is an example of
a monosaccharide.
These are the simple sugars that form the subunit, or monomer, of larger
carbohydrate molecules. They are formed from five or six carbons, and differ
by the groups that attach along these chains:
Monosaccharide
CH2OH CH2OH
O O O
CH2OH OH
H H HO OH
H H
HO
OH H OH H
CH2OH
HO OH H H
H OH OH H OH
Glucose Fructose Galactose
Figure 2 – these three sugars are all hexose, be careful not just to count
the size of the ring, there are carbons attached to this ring too!
What these the three monosaccharides in figure 2 share, are -OH and -H
groups on the left- and right-hand sides of the molecules and it is here that
it becomes possible to connect them and form much larger molecules.
Naming
monosaccharides
Pentose Monosaccharides with five carbons, like
Sugars ribose and deoxyribose are called pentose
sugars (figure 3), while those with six
carbons, like glucose, fructose and galactose,
(figure 2) are called hexose sugars. It is also
important to note the fact that some of these
structures can be arranged differently but
Hexose contain the same atoms, a phenomenon
called isomerism.
Sugars
Glucose for example exists in two forms,
the α-glucose isomer, and the β-glucose
isomer. You can see in figure 4 the slightly
different arrangement of the groups on the
α- and β-isomers.
Ribose Deoxyribose
C5H10O5 C5H10O4
OH CH2 O CH2 O
OH OH OH
C C C C
H H H H
H H H H
C C C C
OH OH OH H
Figure 3 – ribose and deoxyribose, which you will discover
have an important role in protein synthesis and the storage of
genetic information, are both pentose sugars
Glucose
CH2OH CH2OH
H O
C
H H H OH
O O
H C OH
OH H OH C H OH H
H C OH
HO OH HO OH
H C OH
H2C OH
H OH H OH
α-D-glucose β-D-glucose
Figure 4 – the two isomers of glucose. They contain exactly
the same atoms, but a slightly different arrangement of them
Condensation of Monosaccharides
Monosaccharides can be joined through the reaction we met briefly in
topic 1.1, condensation. In this reaction as a bond forms between two simple
sugars, a water molecule is released.
Remember
The opposite of a condensation reaction is hydrolysis. The addition
of water to a disaccharide or polysaccharide allows us to split the
complex sugar back into its constituent simple sugar – the exact
reverse of the condensation reaction.
The bond formed in this process, is called a glycosidic bond. If we look
at the condensation reaction between two molecules of glucose to form
maltose, you can see the glycosidic bond that forms (figure 5).
OH OH
H H H H
O O
OH H
+ OH H
HO OH HO OH
H OH H OH
Glucose Glucose
OH OH
H H H H
O O
OH H OH H
HO OH
H OH H OH
H H
Maltose + Water
Figure 5 – The condensation of two glucose moelcules,
with the new glycosidic bond in the maltose molecule identified
Disaccharides
Disaccharides are the result of a condensation reaction
joining two monosaccharides.
The specific disaccharide that results is down to the combination of the
monosaccharides that join together. As we saw in figure 4, two glucose
molecules join to form maltose, while glucose combining with fructose
will form sucrose, and glucose and galactose form lactose.
Figure 6 shows this in action:
CH2OH
O O
Sucrose
CH2OH
(Glucose – Fructose)
OH OH
OH O
CH2OH
OH OH
CH2OH CH2OH
O O
OH OH
Lactose
O
(Galactose – Glucose) OH OH
OH OH
CH2OH CH2OH
O O
OH
Maltose
(Glucose – Glucose) OH OH
OH O
OH OH
Figure 6
Polysaccharides
When we get to molecules containing more than
two sugars we end up with carbohydrate polymers,
polysaccharides.
Polysaccharides can be huge, starch for example can contain anywhere
between 200 and 100,000 α-glucose monomers!
Polysaccharides fall into different groups based on the
number of monosaccharides that form them:
Disaccharides contain two monosaccharides
Oligosaccharides contain three to six simple sugars
Tip: Polysaccharides are molecules of seven or
more subunits
Polysaccharides like starch are formed in just the same way as disaccharides
– condensation, and they are split by hydrolysis too.
Amylose Amylopectin
Glycogen Cellulose
Figure 7 – large polysaccharides like starch, glycogen
and cellulose, all have different roles to play
Starch
Starch is a polysaccharide with particular importance
in plants and it is found in large amounts in storage
structures like tubers (potatoes) and seeds.
As we saw earlier, it is composed of tens or hundreds of thousands of
α-glucose monomers, and it is the extremely long chain lengths that
allow it to be such an important form of storage. Not only does the chain
length make it insoluble which prevents it from diffusing out of the cells,
this insolubility also prevents it from impacting the water balance between
the cells and their surroundings.
Another benefit of starch as a source of energy is its composition solely of
α-glucose; a simple sugar that is easily obtained as enzymes break down
the different parts of a branched starch molecule, but also α-glucose is
easily metabolised during respiration, providing easy-access energy.
You can see in figure 7 there are two forms of starch; they are the same in
terms of their component atoms, but they have a different overall structure.
One form, amylose, is a single long chain while the other, amylopectin
is branched.
Glycogen
CH2OH CH2OH
O O
OH OH
...O ...O
O O
HO HO
CH2 CH2OH CH2
O O O
OH OH OH
...O
O O O
OH OH OH
7-11
Figure 8
Glycogen is similar in structure to starch, and it is another great energy
storage substance. Where starch is found primarily in plants, glycogen is a
solely animal-derived compound. It too is composed exclusively of α-glucose,
but the chains in glycogen tend to be shorter and there are more branches.
It possesses many of the same attributes that make it equally suited to
energy storage:
Insoluble so it does not affect water balance inside and out of the cell
Large so it cannot diffuse out of the cell – being insoluble helps
with this too
It can be compacted to maximise space
The branches create “ends” that mean multiple enzymes can act
simultaneously to release the α-glucose more quickly for use in respiration
Animals have a much higher metabolic
Did you rate than plants, so it is crucial
that their primary energy storage,
know?
glycogen, is more readily broken down
and glucose available more quickly.
Cellulose
HO HO
O O
O
H H
H H
O
OH H OH H
O H H
H OH H OH
Figure 9
Cellulose is another polysaccharide that is integral in the structures of plants.
It provides the plant with strength and helps to form the cell wall which is
vital in maintaining the plants shape, structure, and osmotic pressure.
It too is composed solely of glucose monomers, but in this case, the β-isomer.
The slight change in the structure of the subunits allows the chains of cellulose
to cross link, that is to bond between parallel chains. It is these cross-links that
create extra strength and rigidity and makes the cellulose perfect for providing
support and rigidity in plant structures like stems and leaves. The cell walls of
the vast majority of plant cells are comprised primarily of cellulose too.
Chemical Tests – Reducing Sugars
Sugars can exist as aither reducing or non-reducing. A reducing sugar can
donate electrons to another molecule or atom (the other species is being
reduced; the sugar is doing the reducing). All monosaccharides are reducing
sugars as well as some disaccharides like maltose.
Reduction and oxidation are chemical reactions that
involve the movement of electrons between reactants.
Oxidation is the loss of electrons
Reduction is the gain of electrons
A reagent that causes another substance to be
oxidised is an oxidiser or it is said to be oxidising
Tip: A reagent that causes another substance to be
reduced is a reducer or it is said to be reducing
We can test for the presence of a reducing sugar using a reagent called
Benedict’s reagent. This is an alkaline solution that contains copper(II) sulfate,
which has a characteristic blue colour. When heated with a reducing sugar the
Benedict’s reagent changes from a blue colour to an orange-brown colour.
Benedict’s Test for Sugars
Benedict’s solution is a deep-blue alkaline chemical reagent
Can be used to detect reducing sugars
Copper sulfate pentahydrate
Benedict’s Sodium carbonate
Solution
Sodium citrate
Step 1 Step 2 Step 3
Benedict’s Add test
Solution sample Heat
Step 4
No sugar Traceable Small Moderate High
Figure 10
The steps for this experiment are critical, without heat
nothing happens so make sure you remember the
different parts of this technique:
01. Add 2cm3 of the test sample to a test tube in liquid form
(solids must be ground down first and mixed with a little water).
02. Add 2cm3 of Benedict’s reagent and shake carefully to mix.
03. Heat the mixture for around five minutes using a suitable heat source
such as a thermostatic water bath.
04. The quantitative test involves watching for a colour change. A colour
change depicts a positive result, no colour change is a negative result.
05. Figure 9 expands on this and shows how you can use the Benedict’s test
semi-quantitatively and give a rough idea of the amount of reducing
sugar present in the sample depending on the colour observed.
Chemical Tests
Distinguishing reducing and non-reducing sugars
Most of the disaccharides are non-reducing, so they would not be detectable
using the conventional Benedict’s test. We can extend it though to allow us to
test for reducing and non-reducing sugars and distinguish between the two.
The method is as follows and starts with the conventional test:
01. Add 2cm3 of test sample to a test tube in liquid form
(solids must be ground down first, with a little water added).
02. Add 2cm3 of Benedict’s reagent and shake carefully to mix.
03. Heat the mixture for around five minutes using a suitable heat source
such as a thermostatic water bath.
04. If there is no colour change at this stage then we do not have a
reducing sugar. What we can do now, is check whether there was
non-reducing sugar in the sample
05. To a second, similar quantity of the food sample, again liquidised, add
2cm3 of dilute hydrochloric acid and heat gently in a water bath, which
helps to hydrolyse any non-reducing sugars present into their
monosaccharides (monosaccharides are reducing!.
06. To the resulting mixture, slowly sodium hydrogen carbonate solution
to neutralise the acid, to allow Benedict’s solution to work.
07. At this point, re-run the Benedict’s test and, if a non-reducing sugar was
present in the original sample, its monosaccharides will now result in a
positive result (that colour change form blue to orange-brown). If there is
still no colour change, then there were no sugars in there at all.
Chemical Tests – Starch
We can also test for the presence of starch in a food
sample by using a solution of iodine and potassium iodide
using the following method:
01. Take 2cm3 of the food sample and place in a test tube.
02. Add two drops of iodine solution (Iodine is dissolved in water in
the presence of potassium iodide to improve its solubility).
03. In the presence of starch the red-brown iodine solution will change
to a deep blue colour.
Iodine Test for Starch
Detect starch or complex carbohydrate in organic sample
02. Observe the colour change
Positive result
Colour change to
deep blue
Sample contains starch
Negative result
01. Few drops of Iodine solution
(Iodine and Potassium iodine) No colour change
on solid/liquid sample No starch in sample
Figure 11
01.
Activity
Identify the monosaccharides present in:
a) Sucrose
b) Maltose
02. Explain the links between the structure and functions of the
following polysaccharides:
a) Starch
b) Cellulose
03. Create a comic strip that shows the steps for testing
for BOTH reducing and non-reducing sugars.
Summary
During this topic we have:
Explained how carbohydrates are formed from
their monomers, monosaccharides.
Identified examples of monosaccharides
including glucose, galactose, and fructose.
Described how condensation reactions create
glycosidic bonds that join monosaccharides.
Outlined the structures of disaccharides and
polysaccharides and the monosaccharides that
form them.
Described the use of chemical tests for sugars
and starch.
Key terms
Carbon backbone – the long chain Polysaccharide – The result
of carbon molecules that runs right of combining two or more
through sugar. monosaccharides to create a much
more complex sugar.
Monosaccharides – the simplest
subunit of sugars, the “monomer”. Cellulose – important in plants,
cellulose is an example of a large
Pentose sugar – A monosaccharide polysaccharide. It contains cross links
that contains 5 carbons. between chains of β-glucose that
increase its strength.
Hexose sugar – A monosaccharide
that contains 6 carbons. Cross-links – these are the links
that occur between chains of
Isomerism – this is where two
monosaccharides in certain
molecules might have the same
polysaccharides.
constituent atoms, and the same
molecular formulae, but the atoms Reducing sugar – this is a sugar that
are arranged in a different way is able to donate electrons to reduce
making different molecules. another substance.
Isomer – isomers are the molecules Benedicts’s reagent – The blue
to which isomerism applies, they reagent, containing copper(II) sulfate,
have the same constituent atoms, that we use to test for the presence
but different arrangement of these. of sugars.
Condensation reaction – the Qualitative – A qualitative test tells if
reaction by which monosaccharides something is there or not.
join to form polysaccharides.
Releases water. Quantitative – A quantitative test is
more in depth and can tell us how
Glycosidic bond – The bond that much is present.
forms between monosaccharides.
