Journal of Lipid Research, Vol 24, 645-651, Copyright © 1983 by Lipid Research, Inc.
Synthesis of conformationally restricted acidic lipids. I. Cyclopentanoid analogs of phosphatidylserine
H Pajouhesh and AJ Hancock
A series of six analogs of phosphatidylserine (PS) was synthesized in which
the conformational mobility of the backbone was limited. Each analog was a
derivative of one of the three diastereoisomeric cyclopentane-1,2,3-triols,
so that the glycerol moiety of the PS was, in effect, replaced by each
cyclopentane-1,2,3-triol. Four of the members of the series were vicinal
dipalmitates [1,2/3-(1P); 1,2/3- (3P); 1,2,3/0-(1P); 1,3/2-(1P)] while the
other two members were "unnatural" in that they contained a 2-phosphate
group. The two 2- phosphate derivatives were meso-forms and each of the
other four derivatives was a DL-pair. Each PS analog was obtained as a
stable microcrystalline precipitate analyzing for the monohydrate of a
mixture of mono- and di-sodium salts. The infrared spectra, melting
behavior, and chromatographic mobility of each sodium salt mixture
resembled those obtained for bovine (glycero-)-phosphatidyl-L-serine; the
stereochemical differences in the ring caused only marginal variation in
these properties. The optical rotation values of the compounds varied with
the stereochemistry of the ring. The all-trans-2-phosphate isomer 8d
exhibited a negative rotation value, in contrast to each of the other
isomers. The all-trans isomer [1,3/2-(1P)] was shown to undergo
diazometholysis with diazomethane to give the dimethyl ester of
cyclopentano-phosphatidic acid.
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