Journal of Lipid Research, Vol 23, 183-189, Copyright © 1982 by Lipid Research, Inc.
Analogs of natural lipids. VII. Synthesis of cyclopentanoid analogs of phosphatidylcholine
AJ Hancock, MD Lister and HZ Sable
A series of six analogs of phosphatidylcholine (lecithin) has been
synthesized, in which the conformational mobility of the backbone is
restricted. The analogs are derivatives of the three diastereoisomeric
cyclopentane-1,2,3-triols and were obtained by triisopropylbenzenesulfonyl
chloride-mediated condensation of isomers of dipalmitoylcyclopentanetriol
phosphate (cyclopentano-phosphatidic acid) with choline tosylate. The
cyclopentano-lecithins obtained include the following: 1,2,3/0-(1P);
1,2,3/0-(2P); 1,2/3-(1P); 1,2/3- (3P); 1,3/2-(1P); 1,3/2-(2P). The two -2P
derivatives are mesoforms while the other four derivatives are DL-pairs.
Each lecithin analog has been obtained as a stable microcrystalline solid.
Elemental analysis indicates that the compounds are hydrated; the data were
consistent with the presence of either one, or in two instances, of
one-half molecule of water of hydration. The infrared spectra, melting
behavior, and chromatographic mobility of each of the analogs resembled
those obtained for dipalmitoyllecithin, but the influence upon physical
properties of stereochemical differences among the analogs was observed
throughout the series.
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