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Lipids Introduction and classification
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Lipids
Introduction
and
classification
1 слайд
Lipids Introduction and classification
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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: CH
3 (CH
2 )
14 - COO -
Non-polar polar
A 16-C fatty acid with one cis double bond between
C atoms 9-10 may be represented as 16:1 cis D 9
.
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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: CH 3 (CH 2 ) 14 - COO - Non-polar polar A 16-C fatty acid with one cis double bond between C atoms 9-10 may be represented as 16:1 cis D 9 .
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Some fatty acids and their common names:
14:0 myristic acid; 16:0 palmitic acid;
18:0 stearic acid; 18:1 cis D 9
oleic acid
18:2 cis D 9,12
linoleic acid
18:3 cis D 9,12,15
a -linonenic acid
20:4 cis D 5,8,11,14
arachidonic acid
20:5 cis D 5,8,11,14,17
eicosapentaenoic acid (an
omega-3) Double bonds in fatty
acids usually have the
cis configuration.
Most naturally
occurring fatty acids
have an even number
of carbon atoms.C
O
O
1
2
3 4
a
fatty acid w ith a cis -D 9
double bond
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Some fatty acids and their common names: 14:0 myristic acid; 16:0 palmitic acid; 18:0 stearic acid; 18:1 cis D 9 oleic acid 18:2 cis D 9,12 linoleic acid 18:3 cis D 9,12,15 a -linonenic acid 20:4 cis D 5,8,11,14 arachidonic acid 20:5 cis D 5,8,11,14,17 eicosapentaenoic acid (an omega-3) Double bonds in fatty acids usually have the cis configuration. Most naturally occurring fatty acids have an even number of carbon atoms.C O O 1 2 3 4 a fatty acid w ith a cis -D 9 double bond
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There is free rotation about C-C bonds in the fatty
acid hydrocarbon, except where there is a double
bond.
Each cis double bond causes a kink in the chain.
Rotation about other C-C bonds would permit a more
linear structure than shown, but there would be a
kink.C
O
O
1
2
3 4
a
fatty acid w ith a cis -D 9
double bond
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There is free rotation about C-C bonds in the fatty acid hydrocarbon, except where there is a double bond. Each cis double bond causes a kink in the chain. Rotation about other C-C bonds would permit a more linear structure than shown, but there would be a kink.C O O 1 2 3 4 a fatty acid w ith a cis -D 9 double bond
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GlycerophospholipidsC O H H
C H 2O H
C H 2O H
g ly c e ro l
Glycerophospholipids
(phosphoglycerides), are common
constituents of cellular
membranes.
They have a glycerol backbone.
Hydroxyls at C1 & C2 are
esterified to fatty acids .
An ester forms
when a hydroxyl
reacts with a
carboxylic acid,
with loss of H
2 O.
Formation of an ester:
O O
R'O H + HO -C -R" R' -O -C -R'' + H 2O
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GlycerophospholipidsC O H H C H 2O H C H 2O H g ly c e ro l Glycerophospholipids (phosphoglycerides), are common constituents of cellular membranes. They have a glycerol backbone. Hydroxyls at C1 & C2 are esterified to fatty acids . An ester forms when a hydroxyl reacts with a carboxylic acid, with loss of H 2 O. Formation of an ester: O O R'O H + HO -C -R" R' -O -C -R'' + H 2O
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Phosphatidate
In phosphatidate :
fatty acids are esterified to hydroxyls on C1 &
C2
the C3 hydroxyl is esterified to P
i .O P O
O
O
H 2 C
C H
H 2 C
O C R 1
O O C
O
R 2
p h o s p h a tid a te
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Phosphatidate In phosphatidate : fatty acids are esterified to hydroxyls on C1 & C2 the C3 hydroxyl is esterified to P i .O P O O O H 2 C C H H 2 C O C R 1 O O C O R 2 p h o s p h a tid a te
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Phosphatidylinositol , with inositol as polar
head group, is one glycerophospholipid.
In addition to being a membrane lipid,
phosphatidylinositol has roles in cell
signaling.O P
O
O
H 2C
C H
H 2C
O C R 1
O O C
O
R 2
O H
H
O H
H
H
O H H
O H
H
O
H O H
phosphatidyl -
inositol
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Phosphatidylinositol , with inositol as polar head group, is one glycerophospholipid. In addition to being a membrane lipid, phosphatidylinositol has roles in cell signaling.O P O O H 2C C H H 2C O C R 1 O O C O R 2 O H H O H H H O H H O H H O H O H phosphatidyl - inositol
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Phosphatidylcholine , with choline as
polar head group, is another
glycerophospholipid.
It is a common membrane lipid. O P O
O
O
H 2C
C H
H 2C
O C R 1
O O C
O
R 2
C H 2 C H 2 N C H 3
C H 3
C H 3
+
p h o s p h a t i d y l c h o l i n e
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Phosphatidylcholine , with choline as polar head group, is another glycerophospholipid. It is a common membrane lipid. O P O O O H 2C C H H 2C O C R 1 O O C O R 2 C H 2 C H 2 N C H 3 C H 3 C H 3 + p h o s p h a t i d y l c h o l i n e
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Each
glycerophospholipid
includes
a polar region:
glycerol , carbonyl
O of fatty
acids, P
i , & the
polar head group ( X )
non-polar
hydrocarbon tails of
fatty acids ( R
1 , R
2 ). O P O
O
O
H 2C
C H
H 2C
O C R 1
O O C
O
R 2
X
g ly c e ro p h o sp h o lip id
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Each glycerophospholipid includes a polar region: glycerol , carbonyl O of fatty acids, P i , & the polar head group ( X ) non-polar hydrocarbon tails of fatty acids ( R 1 , R 2 ). O P O O O H 2C C H H 2C O C R 1 O O C O R 2 X g ly c e ro p h o sp h o lip id
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H 2C
H
C
O H
C H
N + C H
C
C H 2
C H 3
H
H 3
O H
( )12
sphingosineSphingosine may be reversibly
phosphorylated to produce the
signal molecule sphingosine-1-
phosphate .
Other derivatives of sphingosine
are commonly found as
constituents of biological
membranes.Sphingolipids are derivatives of
the lipid sphingosine , which has a
long hydrocarbon tail, and a polar
domain that includes an amino group.
sphingosine -1 -P
H 2C
H
C
O
C H
N + C H
C
C H 2
C H 3
H
H 3
O H
( )12
P O
O
O
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H 2C H C O H C H N + C H C C H 2 C H 3 H H 3 O H ( )12 sphingosineSphingosine may be reversibly phosphorylated to produce the signal molecule sphingosine-1- phosphate . Other derivatives of sphingosine are commonly found as constituents of biological membranes.Sphingolipids are derivatives of the lipid sphingosine , which has a long hydrocarbon tail, and a polar domain that includes an amino group. sphingosine -1 -P H 2C H C O C H N + C H C C H 2 C H 3 H H 3 O H ( )12 P O O O
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H 2C
H
C
O H
C H
N H C H
C
C H 2
C H 3
H
O H
( )12
C
R
O
ceramide
H 2C
H
C
O H
C H
N + C H
C
C H 2
C H 3
H
H 3
O H
( )12
sphingosineIn the more complex
sphingolipids, a polar “head
group" is esterified to the
terminal hydroxyl of the
sphingosine moiety of the
ceramide. The amino group of sphingosine can
form an amide bond with a fatty acid
carboxyl, to yield a ceramide .
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H 2C H C O H C H N H C H C C H 2 C H 3 H O H ( )12 C R O ceramide H 2C H C O H C H N + C H C C H 2 C H 3 H H 3 O H ( )12 sphingosineIn the more complex sphingolipids, a polar “head group" is esterified to the terminal hydroxyl of the sphingosine moiety of the ceramide. The amino group of sphingosine can form an amide bond with a fatty acid carboxyl, to yield a ceramide .
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Sphingomyelin, with a phosphocholine head group, is
similar in size and shape to the glycerophospholipid
phosphatidyl choline. Sphingomyelin has
a phosphocholine or
phosphethanolamine
head group.
Sphingomyelins are
common constituent
of plasma membranes
H 2C
H
C
O
C H
N H C H
C
C H 2
C H 3
H
O H
( )12
C
R
O
P O O
O
H 2
C
H 2
C N +
C H 3
H 3C
C H 3
Sphingomyelin
phosphocholine
sphingosine
fatty acid
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Sphingomyelin, with a phosphocholine head group, is similar in size and shape to the glycerophospholipid phosphatidyl choline. Sphingomyelin has a phosphocholine or phosphethanolamine head group. Sphingomyelins are common constituent of plasma membranes H 2C H C O C H N H C H C C H 2 C H 3 H O H ( )12 C R O P O O O H 2 C H 2 C N + C H 3 H 3C C H 3 Sphingomyelin phosphocholine sphingosine fatty acid
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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.
c erebroside with
-galactose head group
H 2C
H
C C H
N H C H
C
C H 2
C H 3
O H
C
R
O
O H O
H H
H
O H H
O H
C H 2O H
H
O
H
( )12A cerebroside is a
sphingolipid
(ceramide) with a
monosaccharide
such as glucose or
galactose as polar
head group.
A ganglioside is a
ceramide with a polar
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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. c erebroside with -galactose head group H 2C H C C H N H C H C C H 2 C H 3 O H C R O O H O H H H O H H O H C H 2O H H O H ( )12A cerebroside is a sphingolipid (ceramide) with a monosaccharide such as glucose or galactose as polar head group. A ganglioside is a ceramide with a polar
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Cholesterol is largely
hydrophobic .
But it has one polar
group, a hydroxyl ,
making it
amphipathic . C h o l e s t e r o l
H OCholesterol , an
important constituent
of cell membranes,
has a rigid ring
system and a short
branched
hydrocarbon tail.
cholesterol PDB 1N83
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Cholesterol is largely hydrophobic . But it has one polar group, a hydroxyl , making it amphipathic . C h o l e s t e r o l H OCholesterol , an important constituent of cell membranes, has a rigid ring system and a short branched hydrocarbon tail. cholesterol PDB 1N83
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Cholesterol
in membraneCholesterol inserts into bilayer membranes
with its hydroxyl group oriented toward the
aqueous phase & its hydrophobic
ring system adjacent to fatty acid chains of
phospholipids.
The OH group of cholesterol forms hydrogen
bonds with polar phospholipid head groups. C h o l e s t e r o l
H O
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Cholesterol in membraneCholesterol inserts into bilayer membranes with its hydroxyl group oriented toward the aqueous phase & its hydrophobic ring system adjacent to fatty acid chains of phospholipids. The OH group of cholesterol forms hydrogen bonds with polar phospholipid head groups. C h o l e s t e r o l H O
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Бұл курс Қазақстан Республикасы Оқу-ағарту министрлігімен келісілген
