Biomolecules: Module - 7
Biomolecules: Module - 7
Chemistry of Organic
Compounds
Notes
31
BIOMOLECULES
You are aware that our body, plants and other animals are made up of many chemical
substances. There are certain complex organic molecules which form the basis of life.
These build up living organisms and are also required for their growth and maintenance.
Such molecules are called biomolecules. The main classes of biomolecules are
carbohydrates, proteins, lipids, nucleic acids, enzymes, hormones etc. In this lesson, you
will study about the structures and functions of some important biomolecules.
Objectives
After reading this lesson you will be able to :
identify and define different types of biomolecules;
describe the important structural features of biomolecules;
classify carbohydrates, proteins and lipids on the basis of their structure & functions;
give the composition of proteins and nucleic acids;
explain the difference between DNA and RNA;
differentiate between oils and fats;
explain the action of enzymes and their characteristic features and
list the functions of biomolecules in biological systems.
31.1 Carbohydrates
Carbohydrates form a very large group of naturally occurring organic compounds which
play a vital role in daily life. They are produced in plants by the process of photosynthesis.
The most common carbohydrates are glucose, fructose, sucrose, starch, cellulose etc.
Chemically, the carbohydrates may be defined as polyhydroxy aldehydes or ketones
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MODULE - 7 Chemistry
Chemistry of Organic or substances which give such molecules on hydrolysis. Many carbohydrates are
Compounds sweet in taste and all sweet carbohydrates are called as sugars. The chemical name of
the most commonly used sugar in our homes is sucrose.
7 Aldoheptose Ketoheptose
H – C – OH H–C–H
H – C – OH HO – C – H
HO–C–H H – C – OH
H – C – OH
H – C – OH Notes
H – C – OH H – C – OH
H – C – OH
H – C – OH H – C – OH
CH2OH
CH2OH CH2OH CH2OH
O
1 1
C–H H – C – OH
1 HO – C – H
2
H OH 2 O 2
H OH OH O
3 H
HO H 3 3
4 HO H HO H
H OH 4 4
H OH OH
5 H
H OH 5 5
H H
6
CH2OH 6 6
CH2OH CH2OH
6 6
CH2OH CH2OH
O O
5 5
H H H H H OH
4 1 4 1
HO OH H OH HO OH H H
3 2 3 2
H OH H OH
(Ia) (IIa)
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MODULE - 7 Chemistry
Chemistry of Organic The - and -forms of other sugars also exist in the cyclic form. D-Ribose forms a five
Compounds membered ring structure as shown below
HO H2C O H HO H2C O OH
5 5
4 1 4 1
H H H H
Notes 3 2 3 2
H OH H H
OH OH OH OH
– D – ribose – D – ribose
D-before the name of above example indicates the configuration of particular stereoisomer.
Stereoisomers are assigned relative configurations as D– or L –. This system of assigning
the relative configuration refers to their relation with glyceraldehyde. Glyceroldehyde
contains one asymmetric carbon atom so exists in two enantiomeric forms as shown
below.
All those compounds which can be correlated to (+) -glyceraldehyde are said to have
D-configuration and those can be correlated to (–) -glyceraldehyde are said to have
L–configuration. In monosaccharides it is the lowest asymmetric carbon atom (shown in
the box) by which the correlation is made. As in (+) glucose the lowest asymmetric
carbon atom has –OH group on the right side which matches with (+) glyceraldehyde
hence it is assigned D-configuration.
CHO
H OH
HO H
H OH CHO
H OH
H OH
CH2OH
CH2OH
(+) – glucose or (+) – glyceraldehyde or
D-glucose D-glyceraldehyde
CH2OH CH2OH
O O
H H H H H H –H2O Notes
+
HO OH H OH HO OH H OH
H OH H OH
2 molecules of – glucose
CH2OH CH2OH
O O
H H H Glycoside H H H
linkage
O
HO OH H H H OH
H OH H H
Maltose
Similarly, sucrose (the common sugar) consists of one molecule of glucose and one molecule
of fructose joined together. Lactose(or milk sugar) is found in milk and contains one
molecule of glucose and one molecule of galactose.
If a large number of monosaccharide units are joined together, we get polysaccharides.
These are the most common carbohydrates found in nature. They have mainly one of the
following two functions- either as food materials or as structural materials. Starch is the
main food storage polysaccharide of plants. It is a polymer of -glucose and consists of
two types of chains- known as amylose and amylopectin.
Amylose is a water soluble fraction of starch and is a linear polymer of -D-glucose. On
the other hand amylopectin is a water insoluble fraction and consists of branched chain of
-D-glucose.
The carbohydrates are stored in animal body as glycogen which is also a polymer of
-glucose and its structure is similar to amylopectin.
Cellulose is another natural polysaccharide which is the main component of wood and
other plant materials. It consists of long chain of -D-glucose molecules.
Chemistry of Organic (iii) Cell walls of bacteria and plants are made up of cellulose. It may be of interest to note
Compounds that human digestive system does not have the enzymes required for the digestion of
cellulose but some animals do have such enzymes.
(iv) Some carbohydrates are also linked to many proteins and lipids. These molecules are
known as glycoproteins and glycolipids, respectively. These molecules perform very
specific functions in organisms.
Notes
Intext Questions 31.1
1. Name three constituents of your diet which provide carbohydrates.
2. How are carbohydrates produced in nature?
3. What are the hydrolysis products of starch and sucrose?
4. Write the linear and ring forms of D-glucose.
31.2 Proteins
Proteins are the most abundant macromolecules in living cells. The name protein is derived
from the Greek word ‘proteios’ meaning ‘of prime importance’. These are high molecular
mass complex amino acids. You will study about amino acids in the next section. Proteins
are most essential class of biomolecules because they play the most important role in all
biological processes. A living system contains thousands of different proteins for its various
functions. In our every day food pulses, eggs, meat and milk are rich sources of proteins
and are must for a balanced diet.
All proteins found in nature are the polymers of about twenty (20) different -amino acids
and all of these have L-configuration. Out of these ten (10) amino acids cannot be
synthesized by our body and hence must form the part of our diet. These are called
essential amino acids.
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MODULE - 7 Chemistry
Chemistry of Organic All proteins have one common structural feature that their amino acids are connected to
Compounds
O
Notes bond formed when the carboxyl group of one amino acid molecule reacts with the -
amino group of another. In the process, a molecule of water is given off. The product of
the reaction is called a peptide or more precisely a dipeptide because it is made by combining
two amino acids, as shown below:
H O H O
H — N — C — C — OH + H — N — C — C — OH
H R2
H R1
H O H O
H — N — C — C — N — C — C — OH + H2O
H R1 H R2
(A dipeptide)
If a third amino acid is joined to a dipeptide in the same manner, the product is a tripeptide.
Thus, a tripeptide contains three amino acids linked by two peptide linkages. Similar
combinations of four, five, six amino acids give a tetrapeptide, a pentapeptide, a
hexapeptide, respectively. Peptides formed by the combination of more than ten amino
acid units are called polypeptides. Proteins are polypeptides formed by the combination
of large number of amino acid units. There is no clear line of demarcation between
polypeptides and proteins. For example insulin, although it contains only 51 amino acids, is
generally considered a small protein.
The amino acid unit with the free amino group is known as the N-terminal residue and the
one with the free carboxyl group is called the C-terminal residue. By convention, the
structure of peptide or proteins written with the N-terminal residue on the left and the C-
terminal on the right.
The actual structure of a protein can be discussed at four different levels.
(i) Primary structure: Information regarding the sequence of amino acids in a protein
chain is called its primary structure. The primary structure of a protein determines its
functions and is critical to its biological activity.
(ii) Secondary structure: The secondary structure arises due to the regular folding of
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Chemistry of Organic
the polypeptide chain due to hydrogen bonding between and >N – H group.
Compounds
Two types of secondary structures have been reported. These are – helix (Fig.
31.1) when the chain coils up and -pleated sheet (Fig. 31.2) when hydrogen bonds
are formed between the chains.
Notes
.
.. .
O
C One turn of the
C helix; 5.4 Aº per
.
. .. .
O turn (Pitch);
H .. .
O 3.6 amino acids
unit per turn
N H
(Pitch)
. C
.. .
O N
.
.. .
HO
C Carbon
H N
..
C .
.. .
O Oxygen
.
.. .
O
H
Nitrogen
H Side group
N Hydrogen
H N
..
N
..
Fig. 31.1 : The a-helix structure of protein
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Chemistry of Organic
Compounds
Notes
(iv) Quaternary structure: The quaternary structure refers to the way in which simple
protein chains associate with each other resulting in the formation of a complex
protein.
By different modes of bonding in secondary and tertiary structural levels a protein
molecule appears to have a unique three-dimensional structure.
31.2.3 Denaturation
One of the great difficulties in the study of the structure of proteins is that if the normal
environment of a living protein molecule is changed even slightly, such as by a change in
pH or in temperature, the hydrogen bonds are disturbed and broken. When attractions
between and within protein molecules are destroyed, the chains separate from each
other, globules unfold and helices uncoil. We say that the protein has been denatured.
Denaturation is seen in our daily life in many forms. The curdling of milk is caused by
bacteria in the milk which produce lactic acid. The change in pH caused by the lactic
acid causes denaturation, coagulation and precipitation of the milk proteins. Similarly, the
boiling of an egg causes precipitation of the albumin proteins in the egg white. Some
proteins (such as those in skin, fingernails, and the stomach lining) are extremely resistant
to denaturation.
31.3 Lipids
The lipids include a large number of biomolecules of different types. The term lipid
originated from a Greek word ‘Lipos’ meaning fat. In general, those constituents of the
cell which are insoluble in water and soluble in organic solvents of low polarity (such as
chloroform, ether, benzene etc.) are termed as lipids. Lipids perform a variety of biological
functions.
Chemistry of Organic O
Compounds
CH2 — O — C — R1 CH2OH
O
CH — O — C — R2 H O / OH
2
CHOH + R1COOH + R2COOH
O
Notes + R3COOH
CH2 — O — C — R3
CH2OH
(Oil or fat)
Glycerol (Fatty acids)
By definition, a fat is that triglyceride which is solid or semisolid at room temperature and
an oil is the one that is liquid at room temperature. Saturated fatty acids form higher
melting triglycerides than unsaturated fatty acids. The saturated triglycerides tend to be
solid fats, while the unsaturated triglycerides tend to be oils. The double bonds in an
unsaturated triglyceride are easily hydrogenated to give a saturated product, and in this
way an oil may be converted into a fat. Hydrogenation is used in the manufacture of
vanaspati ghee from oils.
Fats and oils are found in both plants and animals. Our body can produce fats from
carbohydrates. This is one method that the body has for storing the energy from unused
carbohydrates. The vegetable oils are found primarily in the seeds of plants.
The second type of simple lipids are waxes. They are the esters of fatty acids with
long chain monohydroxy alcohols 26 to 34 carbons atoms. Waxes are wide-spread in
nature and occur usually as mixtures. They form a protective coating on the surfaces of
animals and plants. Some insects also secrete waxes. The main constitutent of bees wax
obtained from the honey comb of bees is myricyl palmitate:
myricyl palmitate
The waxes discussed above should not be confused with household paraffin wax which is
a mixture of straight chain hydrocarbons.
(ii) Compound Lipids
Compound lipids on hydrolysis yield some other substances in addition to an alcohol
and fatty acids. The first type of such lipids are called phospholipids, because they
are the triglycerides in which two molecules of fatty acids and one molecule of
phosphoric acid are present. Glycolipids contain a sugar molecule in addition to fatty
acid attached to an alcohol.
(iii) Derived Lipids
Steroids are another class of lipids which are formed in our body during metabolism.
These are the compounds with a distinctive ring system that provides the structural
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backbone for many of our hormones. Steroids do not contain ester groups and hence
cannot be hydrolysed. Cholesterol is one of the most widely distributed steroids in
Compounds
animal and human tissues.
H3 C CH3
H3 C Notes
CH3
H3 C
HO (Cholesterol)
Another important group of derived lipids is that of fat-soluble vitamins. This includes
vitamins A, D, E and K, whose deficiency causes different diseases.
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MODULE - 7 Chemistry
Chemistry of Organic protein is to be synthesized? How is this information transmitted from one generation to
Compounds the next? The study of the chemistry of heredity is one of the most fascinating fields of
research today. It was recognized in the 19th century that the nucleus of a living cell
contains particles responsible for heredity, which were called chromosomes. In more
recent years, it has been discovered that chromosomes are composed of nucleic acids.
These are named so because they come from the nucleus of the cell and are acidic in
Notes nature. Two types of nucleic acids exist which are called DNA (deoxyribonucleic acid)
and RNA(ribonucleic acid).They differ in their chemical composition as well as in functions.
— Sugar — phosphate
( — sugar — phosphate
) n
— sugar —
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MODULE - 7 Chemistry
Chemistry of Organic Another important function of nucleic acids is the protein synthesis. The specific sequence
Compounds of bases in DNA represents coded information for the manufacture of specific proteins.
In the process, the information from DNA is transmitted to another nucleic acid called
messenger RNA, which leaves the nucleus and goes to the cytoplasm of the cell. Messenger
RNA acts as template for the incorporation of amino acids in the proper sequence in
protein. The amino acids are brought to the messenger RNA in the cell, by transfer RNA.
Notes Where they form peptide bonds. In short it can be said that DNA contains the coded
message for protein synthesis whereas RNA actually carries out the synthesis of protein.
31.5 Enzymes
In a living system, many complex reactions occur at the temperature of about 310K. An
example of this is the digestion of food, during which stepwise oxidation to CO2 and water
and energy production. These reactions are carried out under such mild conditions due to
presence of certain chemicals which are called enzymes. They act as catalysts for
biochemical reactions in living cells. Almost all the enzymes are globular proteins.
Enzymes are very selective and specific for a particular reaction. They are named after
the compound or class of compounds upon which they work or after the reaction that they
catalyze. The ending of an enzyme name is- ase. For example, maltase is an enzyme that
specifically catalyzes the hydrolysis of maltose into glucose. Similarly, an esterase is an
enzyme which induces hydrolysis of ester linkage.
Notes
Fig. 31.6 : Lock and Key arrangement of enzyme action
complex then breaks to give the molecule of the product and regenerates the enzyme for
the next molecule of the substrate.
Chemistry of Organic Proteins are very important to us and perform many functions in a cell that are
Compounds absolutely necessary for our survival.
Chief sources of proteins are pulses, milk, meat, eggs, etc.
Biomolecules which are insoluble in water and soluble in organic solvents are called
lipids. They are classified as simple, compound and derived lipids.
Nucleic acids are the compound which are responsible for the transfer of characters
Notes from parents to offsprings.
There are two types of nucleic acids- DNA and RNA. They are polymers composed
of repeating units called nucleotides.
DNA contains a five carbon sugar molecule called 2-deoxyribose whereas RNA
contains ribose.
The four bases present in DNA are adenine, cytosine, guanine and thymine whereas
RNA contains uracil in place of thymine.
DNA is a double strand molecule whereas RNA is a single strand molecule.
DNA is present in the nucleus and have the coded message for proteins to be
synthesized in the cell.
Proteins are actually synthesized by RNA which are of three types – messenger-
RNA (m-RNA), ribosomal-RNA (r-RNA) and transfer- RNA (t-RNA).
Enzymes are biocatalysts which speed up the reactions in biosystems.
Chemically all enzymes are proteins. They are very specific and selective in their
action on substrates.
Terminal Exercise
1. How is excess glucose stored in our body?
2. What is a disaccharide? Give an example.
3. What are the products formed by the hydrolysis of lactose?
4. What are essential amino acids?
5. Differentiate between globular and fibrous proteins with suitable examples.
6. What are triglycerides? Mention one of its important uses.
7. What is a nucleotide?
8. Differentiate between the nucleotides of RNA and DNA.
9. What are different types of RNA found in the cell? Mention their functions.
10. What are enzymes?