Fundamentals of Medicinal Chemistry

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Table 1.7 Examples of the classification ofa-phosphatidyl lipids. Common names are
given in brackets

R 2 Classification Glycerol Phosphatidyl glycerol

Choline Phosphatidyl choline
(lecithins)

Inositol Phosphatidyl inositol

Serine Phosphatidyl serine Ethanolamine Phosphatidyl ethanolamine
(a-cephalins)

Thea-phosphatidyl lipids are further subdivided according to the nature of

their R 2 residues (Table 1.7). The R 2 groups of plasmalogens and ether phos-

pholipids are similar to the R 2 groups of the phosphatidyl lipids, whilst the

sphingomyelins have a choline residue.

Phospholipid molecules form the lipid bilayer of cell membranes (Appendix 3).

Plasmalogens and sphingomyelins are particularly abundant in brain tissue.

1.5.7 Glycolipids


Most glycolipids are glycosides with a sphingosine derivative (ceramide) acting

as the aglycone. They are subdivided according to the nature of the carbohy-

drate residue (Table 1.8).

Cerebrosides occur mainly in brain and nervous tissues. Sulphatides are the

main sulpholipids in the brain, where they account for approximately 15%of the

white matter. Gangliosides are particularly abundant in the cells of the central

nervous system. They are believed to be the receptors (Figure A4.1 and Appen-

dix 5) for toxins, such as cholera and tetanus toxins, and some viruses, such as

the influenza virus.

Table 1.8 Examples of the subclassification of glycolipids. R groups are normally long saturated


hydrocarbon chains with 21–25 carbon atoms (a C22–C26 fatty acid residue)


Subclassification Structure


Cerebrosides (neutral glycolipids)


have either a glucose or galactose


carbohydrate residue.


CHCHCHNHCOR

O
OH

O

HOCH 2

H

H
HO

H

H OH

CH 2

CH 3 (CH 2 ) 12 CH

OH

Aβ-D-glucose residue

(continues overleaf)

LIPIDS 25

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