BMS1011

Structure of Biological
Macromolecules
Lipids

Prof. Tanja Junkers

School of Chemistry
Email: tanja.junkers@monash.edu
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Learning outcomes
At the end of this session, you should be able to:

• Identify different classes of lipids including triglycerides,

phospholipids and steroids
• Relate structure of lipids to their physical and chemical properties
• Understand how soaps and detergents work and compare their
behaviour to phospholipids in membranes
• Understand examples of steroids and their functions
Nature’s materials

Carbohydrates

Lipids

Proteins
Lipids
Definition

• Lipids are defined by solubility in nonpolar solvents (a physical

property) rather than by chemical structure.

• There are a great many different kinds and they serve a variety of
functions in the body.

• Many lipids have hydrocarbon or modified hydrocarbon structure,

properties, and behavior.
Lipids
Definition
Lipids
Definition

• Naturally occurring fats and oils are triesters formed between

glycerol and fatty acids.

• Fatty acids are long, unbranched hydrocarbon chains with a

carboxylic acid group at one end. Most have even numbers of
carbon atoms.

• Those without double bonds are saturated.

• Those with double bonds are unsaturated.

• In naturally occurring fats and oils, the double bonds are

usually cis rather than trans.
Lipids
Triacylglycerols

• Animal fats and vegetable oils are the most plentiful lipids in nature.
• Animal fats are solid, whereas vegetable oils are liquid, but their
structures are closely related.
• All fats and oils are composed of triesters of glycerol (1,2,3-
propanetriol = glycerine) with three fatty acids.
• They are named chemically as triacylglycerols, but are often called
triglycerides.
Lipids
Fatty acids
• Fatty acids – long unbranched chain with carboxylic acid group
• Even number of carbons, straight chains
• May have double bonds
Lipids
Fatty acids
• Saturated fatty acids tend to have higher melting points than
unsaturated fatty acids. Due to the difference in the 3D shape of the
hydrocarbon chains
• Double bonds allow the formation of cis- and trans isomers and add
‘kink’ to the hydrocarbon chain = poorer packing and less
intermolecular interactions

A fat
An oil
Lipids
Fatty acids

• The carbon–carbon
double bonds in
vegetable oils can be
hydrogenated to yield
saturated fats.

• This reduces rancidity

• Solid cooking fats are

produced commercially
by hydrogenation of
vegetable oils.
Lipids
Soaps and detergents
• Natural soaps are prepared by boiling lard or other animal fat with
NaOH, a reaction called saponification (Latin: sapo means soap). It is a
ester hydrolysis reaction
Lipids
Definition
• Driven by the hydrophilic and hydrophobic forces, soap
molecules spontaneously self-assemble into micelles

• Soaps work as cleaning agents because the two ends of a

soap molecule are so different. The ionic end is hydrophilic
(water-loving); it tends to dissolve in water. The long
hydrocarbon chain portion of the molecule, however, is
nonpolar and therefore hydrophobic (water-fearing).
Soaps and detergents
Definition

When soap is mixed with water-insoluble grease, oil,

and fat stains, the nonpolar parts of the soap
micelles “dissolve” nonpolar dirt molecules and they
are carried away in the polar wash water.
Soaps and detergents
Definition

• Soaps form water-insoluble salts when used

in water containing Ca2+, Mg2+, and Fe3+ ions
(hard water).
Soaps and detergents
Definition
• The design criteria for a synthetic detergent are
– a long hydrocarbon tail of 12 to 20 carbons.
– a polar head group that does not form insoluble salts with
Ca2+, Mg2+, or Fe3+ ions.
– The most widely used synthetic detergents are the linear
alkylbenzenesulfonates (LAS).
Lipids
Phospholipids
• Phospholipids are the second most
abundant group of naturally
occurring lipids
• Found exclusively in plant and
animal membranes – 40-50%
• Mostly derived from phosphatidic
acid – glycerol esterified with two
fatty acids and one phosphoric
acid
• Further esterification with lower
molecular weight alcohol gives
phospholipid
Lipids
Phospsolipids
• Phospholipids provide the basic structure of cell membranes, where they
aggregate in a closed, sheet-like, double leaflet structure—the lipid bilayer.
Lipids
Phospsolipids
• The bilayer is highly ordered and stable, but still flexible.
• When phospholipids are shaken vigorously with water, they
spontaneously form liposomes—small spherical vesicles with
a lipid bilayer surrounding an aqueous center.
• Hydrophobic effects, which result when nonpolar hydrocarbon
chains cluster to exclude water molecules.
• Electrostatic interactions, which result when polar head groups
interact with water and other polar molecules in the aqueous
environment.
• Water-soluble substances can be trapped in the center of
liposomes, and lipid-soluble substances can be incorporated
into the bilayer.
• Liposomes are potentially useful as carriers for drug delivery
because they can fuse with cell membranes and empty their
contents into the cell.
Lipids
• Fluid mosaic model: A biological membrane
consists of a phospholipid bilayer with
proteins, carbohydrates, and other lipids
embedded on the surface and in the bilayer.
– Fluid signifies that the protein components of
membranes “float” in the bilayer and can move
freely along the plane of the membrane.
– Mosaic signifies that the various components of
the membrane exist side by side, as discrete
units rather than combining to form new
molecules and ions.
Lipids
Lipids
Steroids
• Steroids: A group of plant and animal lipids that have this
tetracyclic ring structure

• Steroid systems are nearly flat and quite rigid

• Cholesterol: Found within the cell membranes – extra

support to prevent phospholipids from ‘gelling’ together
Lipids
Lipid-derived hormones

Androgen
Male sex hormone

Testosterone Androsterone

Anabolic steroids
Promotes tissues and
muscle growth and
development
Methamdriol Nandrolone

Estrogen
Female sex hormones

Progesterone Estrone
Summary and learning outcomes
After this lecture you should be able to:

• Identify different classes of lipids including triglycerides,

phospholipids and steroids
• Relate structure of lipids to their physical and chemical properties
• Understand how soaps and detergents work and compare their
behaviour to phospholipids in membranes
• Understand examples of steroids and their functions