Synthesis of arsinolipids. II. A non-isosteric analogue of fully acylated cardiolipin.

Abstract:

:2-Hydroxypropane-1,3-bis(arsonic acid) after six successive reactions gives the arsinolipid 2-acyloxy-As, As'-bis[2,3-di(acyloxy)propyl]propane-1,3-diylbis(arsinic acid) in 20-40% overall yields. This arsinolipid is a non-isosteric analogue of the fully acylated cardiolipin. The R- and S-glycidol, used to create the backbone of the lipid, give the optically active RR and SS, respectively, arsinolipids, while the rac-glycidol produces a mixture of diastereomers (a racemic pair, RR and SS, and two meso forms with an RS configuration). Some properties of these arsinolipids are described, from which the most interesting are the facile hydrolysis of the middle acyl group and their tendency to absorb environmental water.

journal_name

Chem Phys Lipids

authors

Ioannou PV

doi

10.1016/s0009-3084(02)00009-9

subject

Has Abstract

pub_date

2002-08-01 00:00:00

pages

7-18

issue

1-2

eissn

0009-3084

issn

1873-2941

pii

S0009308402000099

journal_volume

117

pub_type

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