Unit-II Molecules of Life

Chapter 1: Biomolecules: Building Blocks

 Objectives
• Building Blocks of Carbohydrates - Sugars and
their Derivatives
• Building Blocks of Lipids - Simple Fatty Acids,
Glycerol and Cholesterol
• Building Blocks of Proteins - Amino Acids
• Building Blocks of Nucleic Acids – Nucleotides
 Lipids
• Lipids are primarily made up of hydrocarbon
chains connected to glycerol via ester linkage.
• They are hydrophobic and non-polar nature, lipids
are soluble in organic solvents.
• These include fats, triacylglycerols, wax,
phospholipids, steroids, etc.
• Classified into two categories–
1. Simple lipids (eg. Fats, waxes)
2. Compound lipids (eg. Phospholipids, steroids)
 Fatty Acid
• Fatty acids are obtained as a result of hydrolysis of fats.
• Naturally occurring fatty acids are generally synthesized from
two carbon units and hence, contain even number of carbon
atoms.

• Fatty acid chains may be:

1. Saturated (having no double bonds)
2. Unsaturated (having one or more double bonds):
a) Monounsaturated fatty acids: Contains only a single
double bond(eg. oleic acid).
b) Polyunsaturated fatty acids: contain more than one double
bond. eg., Linoleic acid (2 double bonds), Linolenic acid (3
double bonds)
 Structure of Fatty Acid
Saturated Fatty Acid

Unsaturated Fatty Acid

 Symbol for Fatty acids
Fatty acids are denoted by:
• total number of carbon followed by colon (:) and
• then total number of double bonds followed by
• Δ (delta) having superscript number defining the position of the double
bond in parenthesis.
For example a fatty acid with 18 carbon with two double bonds between
C-9 and C-10 and C-12 and C-13 will be denoted as 18:2 (Δ9,12).
4 6 8 11 13 15 17
2

1 3 5 7 9 10 12 14 16 18

18:2 (Δ9,12)
Linoleic acid
 Class Activity

Draw the Structure of:

1. Oleic Acid 18:1 (Δ9)
2. Arachidic Acid 20:0
3. Arachidonic Acid 20:4
(Δ5,8,11,14)
Which one of the above is saturated
fatty acid and why ?
 1. Simple Lipids
• A simple lipid is a fatty acid ester having various alcohols with no
other group (eg., fats and waxes).
(a) Triacylglycerols (known as triglycerides or neutral fats):
• These are the esters of glycerol and fatty acids.
• Simple triglycerides: The triglycerides containing the same fatty
acids in all three ester positions.
• Mixed triglycerides: The triglycerides contain more than one fatty
acid at its three positions.
• Triacylglycerol is essential for providing energy to body.
Triglycerides are a vehicle of energy storage, primarily in adipose
tissue.
(b) Waxes:
• These are esters of fatty acids with a monohydric alcohol of high
molecular weight.
• Wax serves as a protective coating on the surface of animals and
plants, and also reduces water loss in tropical plants.
 Simple Lipids
glycerol

Triacylglycerols esters of
fatty acids

Simple Mixed

Role : Energy Storage

monohydric alcohol (High Mol Wt.)

Wax esters of
fatty acids

Role : Protective Coating

 2. Compound lipids
• Compound lipids are fatty acid esters with alcohols and
• contain additional groups. The fatty acid components
• of these lipids make hydrophobic tails, and the alcohol
• moiety along with additional group constitutes
hydrophilic head
• Such a structure is known as amphipathic molecules.
• Common examples of compound lipids include
• phospholipids and steroids.
 Phospholipids
•A phospholipid is composed of a glycerol
backbone attached on one end to two
fatty acids and the other end has the
esterified phosphoric acid and an organic
alcoholic group.

•It has:
1. polar head group: hydrophilic
composed of esterified
phosphate group and
2. non-polar tail group: hydrophobic or
lipophilic composed of fatty acid
chains

• Phospholipids are primarily found in cell membranes.

 Phospholipids are amphipathic molecules
made up of :
1. two hydrophobic fatty acid tails and
2. a hydrophilic phosphate group head.

Amphiphilic (Greek word-‘amphi’ means “both“; ‘philic’ means “loving“) molecules are
those molecules that have an affinity towards both water molecules as well as lipid
molecules.
Phospholipids are amphipathic or amphiphilic lipids, i.e., the non-polar fatty acid tails
make phospholipid hydrophobic whereas the polar head makes phospholipid hydrophilic.
Being amphiphilic in nature, phospholipid molecules when exposed to water or an
aqueous environment, self-assemble to form bilayer or micellar structure.
Self-assembly is a characteristic feature of phospholipids.
Being amphiphilic in nature, the polar or the water-loving head group tends to move towards
the water molecule while the non-polar, hydrophobic tails tend to move away from the water
molecules.

As a result of this, the phospholipid head and tail form a micellar structure (micelles are
small droplet-like structures). Thus, phospholipid in water has the capability to form micelles.

Further, depending on the condition, these micelles can be single-layer lipidic spheres or
bilayer lipidic spheres (which are better known as liposomes).
Self-assembly of phospholipid molecules depending upon their environment resulting in
the formation of micelles or reverse micelles.
•Micelles:
•Phospholipids do not spontaneously mix with water. Instead, they acquire a sphere-shaped
structure known as micelle.
•Micelles are composed of phospholipids, with hydrophilic head groups forming the outer
shell. Micelles encapsulate water-insoluble drugs in their hydrophobic cores.
•In aqueous environments, lipids form spherical structures in which the hydrophobic tails are
buried in the centre of the structure and hydrophilic head groups are sticking out at the
surface.

Reverse micelles: Reverse micelles form when amphiphilic molecules aggregate in nonpolar
solvents instead of water. In these aggregates, the hydrophilic heads are buried in the core
of the micelle and the hydrophobic tails are on the outside interacting with the solvent.
Lipid bilayers: Phospholipids usually form bilayer having a hydrophobic core and the
hydrophilic heads stick out at the surfaces.
Liposomes: spherical vesicles made of lipid bilayers; they may be used as vehicles for
delivery of drugs and other therapeutic agents into the human body.
Glycerophospholipids:
Phospholipids composed of
fatty acid chains attached to
a glycerol backbone

Sphingophospholipid:
Phospholipids composed of
fatty acid chains attached to
a sphingosine backbone

In sphingolipids, the fatty acid chain is attached to the sphingoid backbone via amide
linkage instead of ester linkage.

The phosphate may further be bound to other molecules, such

as hydrogen, choline, serine, ethanolamine, inositol...
For example in Glycerophospholipids:
If bound to hydrogen: phosphatidic acid
If bound to choline: phosphatidylcholine
If bound to serine: phosphatidylserine

In Sphingolipids:
Ceramide : when the head group contains only a hydrogen atom.
Sphingomyelin: when the head group is phosphocholine.
 Question?
• What is the difference between a micelle and a lipid bilayer?
• Both form organized structures in which one surface is hydrophilic and the other surface is
lipophilic.
• In a simple micele, there is water on one side and oily stuff on the other. These form
enclosed volumes with oil on the inside and water in the supporting medium surounding it.
Inverse micels have water on the inside and oil on the outside
• A lipid bilayer consists of two of these structures sandwiched together such that the lipid
sides of the two are in continuous contact with one another.
• Living cells are spherical water-filled organisms containing a nucleus, mitochondria, and
other components, all inside a lipid bilayre. The bilayer covering has water-soluble
hydrophilic groups, on both the inside and the outside surface, with the lipophilic surfaces
sandwiched together in between the outside of the cell and the inside.
• Synthetic lipid bilayres can be made in the laboratory, and can be used to simulate some of
the actions of living cells.

• Frequently Asked Question: Are lipids hydrophobic or hydrophilic?

Answer: Lipids are hydrophobic i.e., lipids are immiscible with water molecules.
 Question???
• Are phospholipids hydrophobic? … or Are
phospholipids hydrophilic? The presence of
polar (or hydrophilic or water-loving) head
group and non-polar (or hydrophobic or lipid-
loving) tail impart the amphiphilic nature to
these molecules.
A B

C
 Steroids
•Steroids: It has peculiar four-fused ring structure
•Like all the other types of lipids, steroids are
hydrophobic in nature and insoluble in water.

•In a cell, steroids act as receptor ligands and

help to control the metabolism.

• Cholesterol is the most common derivative of steroids.

• Synthesised primarily by the liver, cholesterol is the key precursor of all the
steroid hormones, including testosterone and estradiol.
• Cholesterol is also found in the plasma membrane of cells and provides
rigidity.

Other examples of steroids: phytosterols and stigmasterols (in Plants) which

regulate membrane fluidity and permeability.

Ergosterol (found in Fungi) is an important precursor of vitamin D.