Lipids & Membranes: Biochemistry of Metabolism
Lipids & Membranes: Biochemistry of Metabolism
Lipids & Membranes: Biochemistry of Metabolism
Prepared by LLT
Lipids are non-polar (hydrophobic) compounds,
soluble in organic solvents.
Most membrane lipids are amphipathic, having a
non-polar end and a polar end.
Fatty acids consist of a hydrocarbon chain with a
carboxylic acid at one end.
A 16-C fatty acid: CH3(CH2)14-COO-
Non-polar polar
An ester forms
when a hydroxyl Formation of an ester:
reacts with a
O O
carboxylic acid,
R'OH + HO-C-R" R'-O-C-R'' + H2O
with loss of H2O.
Phosphatidate
O
O H2 C O C R2
R1 C O CH O
H2 C O P O
O
phosphatidate
In phosphatidate:
fatty acids are esterified to hydroxyls on C1 & C2
the C3 hydroxyl is esterified to Pi.
O
O H2C O C R2
R1 C O CH O
H2C O P O X
O
glycerophospholipid
O H 2C O C R2
R1 C O CH O CH3
+
H 2C O P O CH2 CH2 N CH3
O CH3
O H2 C O C R2
R1 C O CH O
H2 C O P O
O H
OH OH
H OH
OH H
phosphatidyl- H H
inositol
H OH
CH3 O OH
Sphingomyelin, a phosphocholine H
H2C C CH
ceramide with a sphingosine NH CH
phosphocholine or
phosphethanolamine O C HC
head group, is a fatty acid R (CH2 )12
common constituent Sphingomyelin CH3
of plasma membranes
galactose as polar O C HC
head group. R (CH2 )12
A ganglioside is a cerebroside with
-galactose head group CH3
ceramide with a polar
head group that is a complex oligosaccharide, including
the acidic sugar derivative sialic acid.
Cerebrosides and gangliosides, collectively called
glycosphingolipids, are commonly found in the outer
leaflet of the plasma membrane bilayer, with their sugar
chains extending out from the cell surface.
OPO3 OH
H2C CH CH
H3N+ CH
HC
phosphorylated H2C O P O
derivatives of O H
6
phosphatidylinositol. OH
1
OPO32
H OH
2 5
Some PH domains OH H
PIP2 H H
bind PIP2 (PI-4,5-P2). phosphatidylinositol- 3 4
H OPO32
4,5-bisphosphate
O
O H2C O C R2
R1 C O CH O
H2C O P O
O H
1 6
OH OH
phosphatidyl- H OH
inositol- 2
OPO3 2
H
5
3-phosphate H H
3 4
H OH
H 3C C CH CH 2 CH 2 C CH CH 2 CH 2 C CH CH 2 S P r o t e in
fa rn e s y l re s id u e lin k e d to p ro te in v ia c y s te in e S
lipid bilayer
Membrane
integral Proteins
CH3 CH3
amino acids: non-polar aliphatic R-groups
CH2 CH2
Tyrosine and
tryptophan are HN
common near the
membrane surface. OH
CH2 CH2
CH2 CH2
CH2 CH2
CH2 NH
NH3 C NH2
NH2
membrane
N C N
A “helical
wheel” looks
down the axis
of an -helix,
projecting side-
chains onto a Polar amino acid R-group
plane. Non-polar amino acid R-group