UNIT-I

Biomolecules
•Introduction
•Classification
•Chemical nature and biological role of carbohydrate, lipids,
lipids
nucleic acids, amino acids and proteins.

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 Introduction

• Lipids (Greek: lipos–fat) are of great importance to the body as

the chief concentrated storage form of energy, besides their role

in cellular structure and various other biochemical functions.

• Lipids may be regarded as organic substances relatively

insoluble in water, soluble in organic solvents (alcohol, ether

etc.), actually or potentially related to fatty acids and utilized

by the living cells.

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Classification of lipids

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 1. Simple lipids
• Simple lipids are esters of fatty acids with alcohols. These are mainly of two
types.

(a) Fats and oils (triacylglycerols):

 These are esters of fatty acids with glycerol.

 The difference between fat and oil is only physical. Thus, oil is a liquid while fat
is a solid at room temperature.

(b) Waxes:

(a) Esters of fatty acids (usually long chain) with alcohols other than glycerol.

(b) These alcohols may be aliphatic or alicyclic.

(c) Cetyl alcohol is most commonly found in waxes.

(d) Waxes are used in the preparation of candles, lubricants, cosmetics, ointments,
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polishes etc.
 2.Complex (or compound) lipids
• These are esters of fatty acids with alcohols containing additional groups such as phosphate,
nitrogenous base, carbohydrate, protein etc.
• They are further divided as follows

(a) Phospholipids: They contain phosphoric acid and frequently a nitrogenous base.

(i) Glycerophospholipids: These phospholipids contain glycerol as the alcohol e.g., lecithin,
cephalin.

(ii) Sphingophospholipids: Sphingosine is the alcohol in this group of phospholipids e.g.,

sphingomyelin.

(b) Glycolipids: These lipids contain a fatty acid, carbohydrate and nitrogenous base. The alcohol
is sphingosine, hence they are also called as glycosphingolipids.

Glycerol and phosphate are absent e.g., cerebrosides, gangliosides.

(c) Lipoproteins: Macromolecular complexes of lipids with proteins.

(d) Other complex lipids: Sulfolipids, aminolipids and lipopolysaccharides are among the other
complex lipids. 5
 3. Derived lipids

• These are the derivatives obtained on the hydrolysis of group 1

and group 2 lipids which possess the characteristics of lipids.

• These include glycerol and other alcohols, fatty acids, mono- and

diacylglycerols, lipid (fat) soluble vitamins, steroid hormones,

hydrocarbons and ketone bodies.

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 4. Miscellaneous lipids

• These include a large number of compounds possessing the

characteristics of lipids

• e.g., carotenoids, squalene, hydrocarbons such as pentacosane (in

bees wax), terpenes etc.

NEUTRAL LIPIDS :

• The lipids which are uncharged are referred to as neutral lipids.

These are mono-, di-, and triacylglycerols, cholesterol and

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cholesteryl esters.
 Functions of lipids
1. They are the concentrated fuel reserve of the body
(triacylglycerols).

2. Lipids are the constituents of membrane structure and regulate the

membrane permeability (phospholipids and cholesterol).

3. They serve as a source of fat soluble vitamins (A, D, E and K).

4. Lipids are important as cellular metabolic regulators (steroid

hormones and prostaglandins).

5. Lipids protect the internal organs, serve as insulating materials

and give shape and smooth appearance to the body.

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 Fatty acids
• Fatty acids are carboxylic acids with hydrocarbon side chain.

• They are the simplest form of lipids.

Occurrence
• Mainly occur in the esterified form as major constituents of
various lipids & also present as free (unesterified) fatty acids.
• Fatty acids of animal origin are much simpler in structure in
contrast to those of plant origin which often contain groups such
as epoxy, keto, hydroxy and cyclopentane rings.

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 Fatty acids
Even and odd carbon fatty acids Saturated & Unsaturated fatty acids
• Most of the fatty acids that occur in • Saturated fatty acids do not contain
natural lipids are of even carbons double bonds, while unsaturated fatty

(usually 14C – 20C). This is due to acids contain one or more double

the fact that biosynthesis of fatty bonds.

acids mainly occurs with the • Both saturated and unsaturated fatty

sequential addition of 2 carbon units. acids almost equally occur in the

natural lipids.
• Palmitic acid (16C) and stearic acid
• Fatty acids with one double bond are
(18C) are the most common.
monounsaturated, and those with 2 or
• Among the odd chain fatty acids,
more double bonds are collectively
propionic acid (3C) and valeric acid
known as polyunsaturated fatty
(5C) are well known.
acids (PUFA).
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 Nomenclature of Fatty acids
• Systematic name & common name

• The saturated fatty acids end with a suffix -anoic (e.g., octanoic acid)
while the unsaturated fatty acids end with a suffix -enoic (e.g.,
octadecanoic acid).

Numbering of carbon atoms

• Carboxyl carbon which is taken as number 1. The carbons adjacent to
this (carboxyl C) are 2, 3, 4 and so on or alternately α, β, γ and so on.
• Starting from the methyl end, the carbon atoms in a fatty acid are
numbered as omega 1, 2, 3 etc.

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 Nomenclature of Fatty acids
Length of hydrocarbon chain of fatty acids (3 groups)

1.Short chain with less than 6 carbons;

2.Medium chain with 8 to 14 carbons and

3.Long chain with 16 to 24 carbons.

Shorthand representation of fatty acids

•The total number of carbon atoms are written first, followed by the number
of double bonds and finally the (first carbon) position of double bonds,
starting from the carboxyl end.
•Thus, saturated fatty acid, palmitic acid is written as 16 : 0, oleic acid as
18 : 1; 9, arachidonic acid as 20 : 4; 5, 8, 11, 14.
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 Nomenclature of Fatty acids
Other conventions of representing the double bonds
•∆9 indicates that the double bond is between 9 and 10 of the fatty acid.
ω 9 represents the double bond position (9 and 10) from the ω end.
Naturally occurring unsaturated fatty acids belong to ω 9, ω 6 and ω 3
series.
•ω 3 series Linolenic acid (18 : 3; 9, 12, 15)

•ω 6 series Linoleic acid (18 : 2; 9, 12) and arachidonic acid (20 : 4; 5, 8,

11, 14)
•ω 9 series Oleic acid (18 : 1; 9)

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Biochemically important saturated & unsaturated Fatty acids

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 Essential Fatty acids
• The fatty acids that cannot be synthesized by the body and, therefore, should be
supplied in the diet are known as essential fatty acids (EFA).
• Chemically, they are polyunsaturated fatty acids, namely linoleic acid (18 : 2;
9, 12) and linolenic acid (18 : 3; 9, 12, 15).
• Arachidonic acid (20 : 4; 5, 8, 11, 14) becomes essential, if its precursor linoleic
acid is not provided in the diet in sufficient amounts.
Biochemical basis for essentiality:
• Linoleic acid and linolenic acid are essential since humans lack the enzymes that
can introduce double bonds beyond carbons 9 to 10.
Functions of EFA:
• Required for the membrane structure and function, transport of cholesterol,
formation of lipoproteins, prevention of fatty liver etc.
• EFA are also needed for the synthesis of eicosanoids.
Deficiency of EFA:
• Phrynoderma or toad skin, characterized by the presence of horny eruptions on
the posterior and lateral parts of limbs, on the back and buttocks, loss of hair and
poor wound healing. 15
 Isomerism in Unsaturated Fatty acids
• Unsaturated fatty acids exhibit geometric isomerism depending
on the orientation of the groups around the double bond axis.
• cis configuration & trans configuration.

• Cis isomers are less stable than trans isomers. Most of the naturally
occurring unsaturated fatty acids exist as cis isomers.

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 Triacylglycerols
• Triacylglycerols (formerly triglycerides) are the esters of glycerol with fatty
acids.
• The fats and oils that are widely distributed in both plants and animals are
chemically triacylglycerols.
• They are insoluble in water and non-polar in character and commonly known as
neutral fats.

Fats as stored fuel:

• Triacylglycerols are the most abundant group of lipids that primarily function as
fuel reserves of animals.

Fats primarily occur in adipose tissue:

• Adipocytes of adipose tissue—predominantly found in the subcutaneous layer
and in the abdominal cavity—are specialized for storage of triacylglycerols. 17
 Structures of Acylglycerols
• Monoacylglycerols, diacylglycerols and triacylglycerols, respectively consisting of one, two
and three molecules of fatty acids esterified to a molecule of glycerol. Among these,
triacylglycerols are the most important biochemically.
• Simple triacylglycerols contain the same type of fatty acid residue at all the three carbons e.g.,
tristearoyl glycerol or tristearin.
• Mixed triacylglycerols are more common. They contain 2 or 3 different types of fatty acid
residues. In general, fatty acid attached to C1 is saturated, that attached to C2 is unsaturated
while that on C3 can be either. Triacylglycerols are named according to placement of acyl
radical on glycerol e.g., 1,3-palmitoyl 2-linoleoyl glycerol.

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 Phospholipids
These are complex or compound lipids containing phosphoric acid,
in addition to fatty acids, nitrogenous base and alcohol.
Glycerophospholipids Sphingophospholipids
• Glycerophospholipids (or
• Sphingophospholipids (or
phosphoglycerides) that contain
glycerol as the alcohol. sphingomyelins) that contain
 Phosphatidic acid
sphingosine as the alcohol.
 Lecithins (phosphatidylcholine)
 Cephalins
(phosphatidylethanolamine)
 Phosphatidylinositol
 Phosphatidylserine
 Plasmalogens
 Cardiolipin

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 Lipoproteins

• Lipoproteins are molecular complexes of lipids with proteins. They are

the transport vehicles for lipids in the circulation.

• There are five types of lipoproteins, namely

i. Chylomicrons

ii. Very low density lipoproteins (VLDL)

iii. Low density lipoproteins (LDL)

iv. High density lipoproteins (HDL) and

v. Free fatty acid albumin complexes. 20

• Steroids are the compounds containing a cyclic Steroids
steroid nucleus (or ring) namely
cyclopentanoperhydrophenanthrene (CPPP).
• It consists of a phenanthrene nucleus (rings A, B and
C) to which a cyclopentane ring (D) is attached.
• The methyl side chains (19 & 18) attached to
carbons 10 & 13 are shown as single bonds. At
carbon 17, steroids usually contain a side chain.
• Several steroids in the biological system include
cholesterol, bile acids, vitamin D, sex hormones,
adrenocortical hormones, sitosterols, cardiac
glycosides and alkaloids.
• If the steroid contains one or more hydroxyl groups
it is commonly known as sterol (means solid
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alcohol).