Biomolecules

A living organism is composed of complex organic substances known as Biomolecules.

This chapter discusses in detail some of the important biomolecules.
In this chapter , we discuss about one of the most important biomolecules, namely
Carbohydrates. Most of the questions in competitive exams are asked from the
carbohydrate section and students are requested to be thorough in this chapter.

Carbohydrates

Carbohydrates are compounds which can be mainly written as Cx(H2O)y. However,

there are exceptions which might encounter in this chapters.

Classification of Carbohydrates

Classification 1

Carbohydrates are classified into monosaccharides, oligosaccharides and

Polysaccharides.

Monosaccharides are those carbohydrates which cannot be broken down further by

hydrolysis.
Some common examples of monosaccharides are Glucose, Fructose and Galactose.

Oligosaccharides yield 2 to 10 monosaccharides on hydrolysis.

Some common examples of oligosaccharides are Sucrose, Lactose and Maltose.

Polysaccharides yield more than 10 monosaccharides on hydrolysis.

Common examples are starch, glycogen and cellulose.

Classification 2

Carbohydrates are classified into sugars and non sugars.

Sugar are
1) Sweet in taste
2) Soluble in water
3) Crystalline form
Non sugar
1) Tasteless
2) Readily soluble in nonpolar solvents
3) Amorphous form

Classification of sugars

Sugars are further classified into reducing and non reducing sugars.

Reducing sugars
1) Reduce tollens and Fehlings solution
2) Present in Hemiacetal/ Hemiketal form
3) Exhibit tautomerism
4) Exhibit mutarotation
5) Can form osazone/oximes

Non reducing sugars

1) Do not reduce tollens and fehlings
2) Present in acetal/ketal form
3) Do not exhibit tautomerism
4) Exhibits mutarotation
5) Can form osazone/oximes

D-L configuration

You have already studied about D-L configurations in the chapter Isomerism.

All naturally occurring carbohydrates occur in D form.

Hence we usually deal with D sugars.

D sugars - D aldoses
D ketoses.

Note: The pair of sugars (stereoisomers) which are derived from same sugar units but
differ at configuration only at the 2nd carbon at the top are referred to as epimers.
Carbohydrate charts
The following two charts will give complete information about most of the carbohydrates
we will be dealing with in this chapter.
Important: The chart is arranged in such a way that we introduce a new carbon in each
stage. The left one contains -OH in the right and the right one contains -OH in the left in
each stage as you will see.

D-Aldoses

D - glyceraldehyde

D - erythrose D - Threose

D - Allose D-Arabinose D-Lyxose D- Lyxose

D- D- D- D- D- D- D- D-
Glucose Altrose Glucose Mannose Gulose Idose Galactose Talose
 Dihydroxyacetone

D-Erythrulose

D-Ribulose D-Xylulose

D - Psicose D - Fructose D - Sorbose D - Tagatose

Monosaccharides

1) D - Glucose/ Dextrose sugar

Molecular formula: C6H12O6

Molecular Weight: 180
C to H ratio: 1:2

From several reaction, it was assumed that Glucose had an open chain structure like
the one below.

Limitations of the open chain structure of glucose

1) Even though the - CHO group is present, it doesnt react with NaHSO3 , NH3 or
Schiffs reagent
2) Does not account for Mutarotation
3) It only consumes one mole of alcohol to form acetals( instead of two) to form
acetals.

Cyclic Structure

Intramolecular nucleophilic addition takes place to form the cyclic structure as given
below.
But there are two possible configurations of cyclic structures based on whether the OH
in the 2nd carbon is on top or on the bottom. These two cyclic forms of Glucose are
called D Glucopyranose and D Glucopyranose respectively.

Glucopyranose Glucopyranose

The diastereomers which differ in configuration at newly generated chiral carbon are
called anomeric pair.
Eg : Glucopyranose and Glucopyranose

D- Fructose

Molecular formula: C6H12O6

Molecular weight: 180 g/mol
C:H : 1:2

Similar to Glucose , Fructose has both an open chain structure and 2 anomeric cyclic
structures.

The cyclic forms are called - D Fructofuranose and D Fructofuranose

respectively.

- D Fructofuranose D Fructofuranose
Disaccharides

1)Sucrose

Molecular formula: C12H22O11

Common name: Cane sugar

Hydrolysis of Sucrose yields one glucose and one fructose.

This process is called inversion of cane sugar.
It is called as inversion of cane sugar because on hydrolysis , the dextrorotatory
sucrose gives a levorotatory fructose and a dextrorotatory glucose. But the levorotatory
nature of Fructose dominates and hence the net result is levorotation.
Hence it is referred to as inversion of cane sugar.

Sucrose consists of one unit of - D glucopyranose and one - D Fructofuranose

They are linked by a glycosidic bond ie a C-O-C bond formed by the removal of a water
molecule

Here one carbon is in acetal and other in ketal form. As you might know, acetals and
ketals don't get converted into base on hydrolysis. Hence, sucrose is a non reducing
sugar.

2) Maltose

Maltose on hydrolysis gives two units of Glucose.

Maltose consists of two units of - D Glucopyranose
The linkage is between carbon 1 of one and Carbon 4 of the other by a glycosidic bond.

Unlike Sucrose these are reducing sugars.

3)Lactose

Lactose on hydrolysis gives one molecule of glucose and one molecule of Galactose.

The linkage is between C 1 of - D Galactopyranose and C 4 of - D glucopyranose.

Polysaccharides

1) Cellulose

Cellulose contains n units of D Glucopyranose linked by C1 of one molecule and C4

of the other molecule.

Cellulose is mainly found in plant cells

2) Starch

Starch is also composed of n units of Glucose.

Starch is composed of amylose and amylopectins.

1) Amylose are linear and water soluble. They compose 10 - 20% of Starch.
2) Amylopectins are branched and water insoluble. They consist 80-90% of starch.
In plants, carbohydrate is stored as starch.

Tests for identification of Carbohydrates

1) Benedict's test - Gives red precipitate

2) Iodine test - Only by starch ( gives blue colour)
3) Alcoholic Naphthol - Purple colour.