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BIOCHEMISTRY

ASSIGNMENT-1

STRUCTURAL AND FUNCTIONAL


RELATIONSHIP OF
CARBOHYDRATES

Sharon. C. Varghese
08FA107
II-BIOTECH ‘B’

The term carbohydrate was originally used to describe compounds that were
literally "hydrates of carbon" because they had the empirical formula CH2O.
In recent years, carbohydrates have been classified on the basis of their
structures, not their formulas. They are now defined as polyhydroxy
aldehydes and ketones. Among the compounds that belong to this family are
cellulose, starch, glycogen, and most sugars.
There are three classes of carbohydrates: monosaccharides, disaccharides,
and polysaccharides. The monosaccharides are white, crystalline solids
that contain a single aldehyde or ketone functional group. They are
subdivided into two classes aldoses and ketoses on the basis of
whether they are aldehydes or ketones. They are also classified as a triose,
tetrose, pentose, hexose, or heptose on the basis of whether they contain
three, four, five, six, or seven carbon atoms.
With only one exception, the monosaccharides are optically active
compounds. Although both D and L isomers are possible, most of the
monosaccharides found in nature are in the D configuration. Structures for
the D and L isomer of the simplest aldose, glyceraldehyde, are shown below.

D- L-
Glyceraldehyd Glyceraldehyd
e e

I. The Basic Structure of Monosaccharides


II. The structures of many monosaccharides were first determined by
Emil Fischer in the 1880s and 1890s and are still written according
to a convention he developed. The Fischer projection represents
what the molecule would look like if its three-dimensional structure
were projected onto a piece of paper. By convention, Fischer
projections are written vertically, with the aldehyde or ketone at the
top. The -OH group on the second-to-last carbon atom is written on
the right side of the skeleton structure for the D isomer and on the
left for the L isomer. Fischer projections for the two isomers of
glyceraldehyde are shown below.

D- L-
Glyceraldehyd Glyceraldehyd
e e
III. These Fischer projections can be obtained from the skeleton
structures shown above by imaging what would happen if you
placed a model of each isomer on an overhead projector so that the
CHO and CH2OH groups rested on the glass and then looked at the
images of these models that would be projected on a screen.
The basic feature that makes an aldose different from a ketose is the
position of the carbonyl group of the monosaccharide. As seen below, an
aldose has the carbonyl group at Carbon #1 (affording an aldehyde) while a
ketose has the carbonyl group at Carbon #2 (affording a ketone).

For an aldose the carbonyl carbon is always carbon-1. When the aldose is
drawn in a fisher projection (as above) you would then continue to number
the carbons as you go down the chain. For a ketose the numbering rules are
similar. Therefore, the ketose above has the ketone at carbon-2, as will any
ketoses that you need to worry about for this class.
The (HCOH)n simply represents more hydroxyl substituted carbons in the
monosaccharide structure. The total number of carbons can be used to
classify the aldoses and ketoses by using Aldo- or Keto- followed by
numerical prefixes attached to an -ose.

The above sugars are all "D". Therefore, the hydroxyl group on the
asymmetric carbon furthest from the carbonyl group is to the 'right' in the
fisher projection. An "L" sugar would have the opposite stereochemistry at
that carbon.
Below you will see how an alcohol and an aldehyde combine to form a
hemiacetal. In a similar fashion, this reaction occurs with the sugars to give
the ring forms.

So, from a fisher projection of a monosaccharide we can draw two possible


cyclic forms (Haworth Projections), the alpha and the beta. These two differ
only by the stereochemistry of the hydroxyl group at the anomeric carbon.
A similar strategy is also used for ketoses and the formation of cyclic
ketoses. The alcohol and the ketone combine to form a hemiketal. In the
case of the ketohexose, hemiketal at the anomeric carbon affording a five
member called a ketofuranose.

Well, not every monosaccharide is simply a bunch of hydroxyl groups


attached to carbon atoms. In fact, the monosaccharides can be modified in
many ways to give of a variety of structural derivatives.
One important point is that the monosaccharides (and therefore larger
oligosaccharides and polysaccharides) can have a variety different
substituents in place of hydroxyl groups.
These added functional groups may also serve specific functions such as:
alter the sugars physical characteristics, play a role in how the sugar
interacts with other biomolecules, or provide a reactive functional group on
the sugar for further modification in the body.
From this figure the different modified monosaccharides can be
identified.
You should also notice that, in most cases, you could still convert the
above fisher projections into the cyclic Haworth projections (as shown
for D-Glucuronic acid). However, some of the derivatives such as the
alditol and the aldonic acid can not cyclize to form a hemiacetal since
they no longer have a C-1 aldehyde.
The oxidation of D-glucose to D-gluconic acid. This oxidation reaction is
used to monitor blood glucose levels and is displayed below. Glucose
oxidase converts oxygen and glucose to hydrogen peroxide and gluconic
acid. The hydrogen peroxide then reacts with a dye in the test to form a
colored dye that can be quantitated which tells you how much glucose is
in the blood.

This test also relies on the formation of aldonic acids from an aldose
as shown below.