Definition:
Carbohydrates are hydrates of carbon, which on hydrolysis produce polyhydroxy aldehydes or polyhydroxy ketones.
OR
Carbohydrates are the derivatives of the polyhydroxy aldehydes or ketones or the products derived from them.
Physical Properties of Carbohydrates:
Asymmetric carbon atom
A carbon atom to which four different atoms or groups of atoms are attached is said to be an asymmetric carbon atom.
Many biochemicals contain two or more asymmetric carbon atoms.
The presence of asymmetric carbon atom allows formation of isomers.
The compounds which have the same structural formula, but differ only in spatial configuration are called stereo-isomers or geometric isomers.
More the number of asymmetric carbon atoms, more are the number of isomers;
e.g. glucose with four asymmetric carbon atoms has 2"= 2 = 16 isomers; n indicates the number of asymmetric carbon atoms.
If the molecule contains one double bond with two different atoms or groups of atoms linked with every carbon, then there exists cis-trans isomerism.
Since the double bond is rigid, the atoms attached to it are not free to rotate like those attached to a single bond.
The example of cis-maleic acid and trans-fumaric acid on a planar form are show here. These isomers have different chemical and physiological properties; e.g. fumaric acid is physiologically active.
Classification of Carbohydrates Isomers:
Isomers of carbohydrates are classified as follows:
D and L isomers.
Optical isomers.
Epimers.
Anomers.
D and L isomers:
When the -OH group around the carbon atom adjacent to the terminal primary alcohol carbon (carbon 5 in case of glucose) is on the right side, the sugar belongs to the D-series.
If the hydroxyl group is on the left side, it is a member of the L-series.
Majority of monosaccharides in mammals are of D configuration.
Optical isomers:
When a beam of polarized light is passed through a solution exhibiting optical activity, it will be rotated to the right or left in accordance with the presence of the optical isomer.
A compound which causes rotation of polarized light to the right is said to be dextro-rotatory and is designated with a plus (+) sign.
Rotation of the beam to the left is termed as laevo-rotatory and is designated by the minus (-) sign.
Stereoisomerism and optical isomerism are independent properties.
Epimers:
Isomers formed as a result of interchange of -OH and -H on carbon atoms 2, 3 and 4 of glucose are known as epimers.
In the body, epimerization takes place by the enzyme epimerase.
Anomers:
The cyclic structure of glucose is retained in solution, but isomerism takes place about position 1.
This is accomplished by optical rotation (mutarotation) by which the positions of -H and -OH groups are changed around carbon 1.
Inter-conversion of A and B glucose in solution with change of optical activity is called mutarotation.
It is explained by the A and B form of glucose requiring the presence of asymmetric carbon C.
Commonly Asked Questions.
Define carbohydrates and write a note on different Isomers of Carbohydrates.