Beruflich Dokumente
Kultur Dokumente
ASSIGNMENT-1
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
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.
This test also relies on the formation of aldonic acids from an aldose
as shown below.