Journal of Lipid Research, Vol 18, 81-92, Copyright © 1977 by Lipid Research, Inc.
Analogs of natural lipids. IV. Synthesis and properties of cyclopentanoid analogs of phosphatidic acid
AJ Hancock, MH Stokes and HZ Sable
A new series of phosphatidic acid analogs has been synthesized in which the
glycerol moiety of diacylglycerophosphoric acid is replaced by each of the
three isomeric cyclopentane-1,2,3-triols (1,3/2, DL-1,2/3, and 1,2,3/0). Of
the seven possible configurational and positional phosphatidic acid analogs
of this series, five isomers have been obtained and characterized by
spectroscopic methods and microanalysis. Four of the five isomers are 1-(or
3-)phosphoryl derivatives, while the fifth is a 2-phosphate. The analogs
were prepared in configurationally pure form by unequivocal synthetic
procedures involving selectively blocked intermediates: acyl migration was
avoided by the use of mild deblocking procedures. The anhydrous lipid
products, all of which are dipalmitoyl esters, are solids indefinitely
stable at room temperature in the free acid or potassium salt form; they
have chromographic mobility and melting points similar to dipalmitoyl
glycerophosphoric acid the dipotassium salts bind water of hydration
tenaciously, remaining hydrated after drying in vacuo at 100 degrees C. NMR
spectra of dimethyl esters of some of the analogs show nonequivalence of
the two methyl groups, consistent with the diastereotopic nature of those
groups. In addition to their intrinsic interest as conformationally
restricted acidic lipids, the analogs are now available as starting
materials for the synthesis of the more complex acidic and amphoteric
lipids required for our exploitation of these cyclopentanoid analogs as
unique probes for the study of lipid-lipid and protein-lipid interactions.
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