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114

PANEL 25: Fatty Acids and Other Lipids

COMMON FATTY
ACIDS

TRIACYLGLYCEROLS
O

These are carboxylic acids


with long hydrocarbon tails.
COOH

COOH

COOH

CH2

CH2

CH2

CH2

CH2

CH2

CH2

CH2

CH2

CH2

CH2

CH2

CH2

CH2

CH2

CH2

CH2

CH2

CH2

CH2

CH2

CH2

CH2

CH

CH2

CH2

CH

CH2

CH2

CH2

CH2

CH2

CH2

CH2

CH2

CH2

CH2

CH2

CH2

CH2

CH2

CH2

CH2

CH3

CH2

CH2

palmitic
acid
(C16)

CH2

CH3
stearic
acid (C18)

CH3
oleic
acid (C18)

H2C

HC

H2C

Fatty acids are stored as an energy reserve (fats and


oils) through an ester linkage to glycerol to form
triacylglycerols, also known as triglycerides.

C
O

H 2C

OH

HC

OH

H 2C

OH

glycerol

Hundreds of different kinds of fatty acids exist. Some have one or more double bonds in their
hydrocarbon tail and are said to be unsaturated. Fatty acids with no double bonds are saturated.
O
O
O
O
C

This double bond


is rigid and creates
a kink in the chain.
The rest of the chain
is free to rotate
about the other CC
bonds.

oleic
acid

space-filling model

carbon skeleton

UNSATURATED

CARBOXYL GROUP

SATURATED

PHOSPHOLIPIDS

Phospholipids are the major constituents


of cell membranes.

If free, the carboxyl group of a


fatty acid will be ionized.

hydrophilic
group

choline

C
O

stearic
acid

P
O

CH2

CH

CH2

But more usually it is linked to


other groups to form either esters
O
C
O

C
hydrophobic
fatty acid tails

or amides.

space-filling model of
the phospholipid
phosphatidylcholine

O
C
N
H

general structure
of a phospholipid

In phospholipids two of the OH groups in glycerol are


linked to fatty acids, while the third OH group is linked
to phosphoric acid. The phosphate is further linked to
one of a variety of small polar groups (alcohols).

CHAPTER 2 PANELS

115

POLYISOPRENOIDS

LIPID AGGREGATES

long-chain polymers of isoprene


Fatty acids have a hydrophilic head
and a hydrophobic tail.
O

micelle

In water they can form a surface film


or form small micelles.

Their derivatives can form larger aggregates held together by hydrophobic forces:
Triglycerides can form large spherical
fat droplets in the cell cytoplasm.

Phospholipids and glycolipids form self-sealing lipid


bilayers that are the basis for all cell membranes.

200 nm
or more

4 nm

OTHER LIPIDS

STEROIDS

Lipids are defined as the water-insoluble


molecules in cells that are soluble in organic
solvents. Two other common types of lipids
are steroids and polyisoprenoids. Both are
made from isoprene units.

CH3
C
CH2

CH

CH2

isoprene

Steroids have a common multiple-ring structure.


OH

HO

cholesterolfound in many membranes

testosteronemale steroid hormone

GLYCOLIPIDS
Like phospholipids, these compounds are composed of a hydrophobic
region, containing two long hydrocarbon tails, and a polar region,
which, however, contains one or more sugars and no phosphate.

galactose

OH

C
H

H
C

C NH
hydrocarbon tails

O
CH2

sugar

a simple
glycolipid

dolichol phosphateused
to carry activated sugars
in the membrane-associated
synthesis of glycoproteins
and some polysaccharides