Sphingolipids

Dr. Abir Alghanouchi

Biochemistry department
Sciences college

Sphingolipids make up the second largest class of
phospholipids.

The most distinct difference between sphingolipids

and glycerophospholipids is that the backbone of
sphingolipids is NOT glycerol.

Sphingolipids contain:
1. Sphingosine (shown in red), which is a long-chain
amino alcohol:18- carbon amino alcohol with C-C
double bond
2. A fatty acid is joined to sphingosine via an amide
linkage rather than an ester linkage as seen in glycerol.

Sphingosine may be reversibly OH OH
H
phosphorylated to produce the signal H2C C CH
molecule sphingosine-1-phosphate H3N+ CH

O HC

O P O
(CH2 )12
O OH
sphingosine CH3
H
H 2C C CH

H3N+ CH

HC
Other derivatives of sphingosine

(CH2 )12
are commonly found as
sphingosine-1-P constituents of biological
CH3
membranes.
 OH OH

The amino group of sphingosine can H
form an amide bond with a fatty acid H2C C CH
carboxyl, to yield a ceramide. H3N+ CH

HC
OH OH
(CH2 )12
H
H2C C CH
sphingosine CH3
NH CH

O C HC
In the more complex sphingolipids, a

polar head group" is esterified to the
R (CH2 )12
terminal hydroxyl of the sphingosine
ceramide CH3 moiety of the ceramide.

Sphingomyelin has a CH3 O
H2 H2
phosphocholine or H3 C N +
C C O P O
phosphoethanolamine
CH3 O OH
head group. phosphocholine H
H2C C CH
sphingosine NH CH

Sphingomyelins are common
constituent of plasma O C HC

membranes fatty acid R (CH2 )12

Sphingomyelin CH3

Sphingomyelin, with a phosphocholine head group, is

similar in size and shape to the glycerophospholipid
phosphatidyl choline.
 CH2OH

OH O
H OH
OH H O
H
H H H2C C CH

H OH NH CH

O C HC

R ( CH2 )12
cerebroside with
-galactose head group CH3

A cerebroside is a sphingolipid (ceramide) with a

monosaccharide such as glucose or galactose as
polar head group.

Sulfatide: Sugar is galactose with sulfate esterified
at carbon 3 of galactose

A ganglioside is a ceramide with a polar head group

that is a complex oligosaccharide, including the
acidic sugar derivative sialic acid.

Cerebrosides, sulfatide and gangliosides, collectively

called glycosphingolipids
 Non
Ceramide is a precursor for sphingolipids
numerous glycosphingolipids:

One well-known function of
sphingolipids is that they function as
cell surface antigens, defining the
various blood types.

The human blood groups are
determined in part by the type of
sugars located on the head groups.

If the gene encodes a protein that
transfers an N-acetylgalactosamine
group, this corresponds to the A
antigen.

If the gene encodes a protein that
transfers a galactose group, this
corresponds to the B antigen.

If the gene does not encode an

active glycosyltransferase, this
corresponds to the O antigen.