Download Panel 2–4 Fatty acids and other lipids

Panel 2–4 Fatty acids and other lipids
FATTY ACIDS
All fatty acids have carboxyl groups
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)
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
C
oleic
acid
space-filling model
This double bond
is rigid and creates
a kink in the chain.
The rest of the chain
is free to rotate
about the other C–C
bonds.
stearic
acid
carbon skeleton
UNSATURATED
TRIACYLGLYCEROLS
O
H 2C
CH3
oleic
acid
(C18)
O
HC
O
H2C
O
CARBOXYL GROUP
SATURATED
Fatty acids are stored as an energy reserve
(fats and oils) through an ester linkage to
glycerol to form triacylglycerols.
H2C
OH
C
HC
OH
O
H2C
OH
C
glycerol
O
C
Phospholipids are the major constituents
of cell membranes.
PHOSPHOLIPIDS
hydrophilic
group
If free, the carboxyl group of a
fatty acid will be ionized.
choline
O
O
O
C
_
_
O
P
O
O
CH2
CH
CH2
But more often it is linked to
other groups to form either esters
O
C
O
C
hydrophobic
fatty acid tails
or amides.
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).
LIPID AGGREGATES
POLYISOPRENOIDS
long-chain polymers
of isoprene
Fatty acids have a hydrophilic head
and a hydrophobic tail.
O–
micelle
O
In water they can form a surface film
or form small micelles.
P
O–
O
Their derivatives can form larger aggregates held together by hydrophobic forces:
Triglycerides form large spherical fat
droplets in the cell cytoplasm.
Phospholipids and glycolipids form self-sealing lipid
bilayers that are the basis for all cellular 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
O
cholesterol—found in many membranes
testosterone—male 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 sugar residues and no phosphate.
H
OH
C
C
C
H
H
H
C
C NH
hydrocarbon tails
O
galactose
O
CH2
sugar
residue
a simple
glycolipid
dolichol phosphate—used
to carry activated sugars
in the membrane-associated
synthesis of glycoproteins
and some polysaccharides