Analogs of natural lipids. VII. Synthesis of cyclopentanoid analogs of phosphatidylcholine.

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...

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Main Authors: A J Hancock, M D Lister, H Z Sable
Format: Article
Language:English
Published: Elsevier 1982-01-01
Series:Journal of Lipid Research
Online Access:http://www.sciencedirect.com/science/article/pii/S0022227520381876
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spelling doaj-62e9d65e44bb4a9fbb4c8ccb7835cf132021-04-24T05:51:08ZengElsevierJournal of Lipid Research0022-22751982-01-01231183189Analogs of natural lipids. VII. Synthesis of cyclopentanoid analogs of phosphatidylcholine.A J HancockM D ListerH Z SableA 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.http://www.sciencedirect.com/science/article/pii/S0022227520381876
collection DOAJ
language English
format Article
sources DOAJ
author A J Hancock
M D Lister
H Z Sable
spellingShingle A J Hancock
M D Lister
H Z Sable
Analogs of natural lipids. VII. Synthesis of cyclopentanoid analogs of phosphatidylcholine.
Journal of Lipid Research
author_facet A J Hancock
M D Lister
H Z Sable
author_sort A J Hancock
title Analogs of natural lipids. VII. Synthesis of cyclopentanoid analogs of phosphatidylcholine.
title_short Analogs of natural lipids. VII. Synthesis of cyclopentanoid analogs of phosphatidylcholine.
title_full Analogs of natural lipids. VII. Synthesis of cyclopentanoid analogs of phosphatidylcholine.
title_fullStr Analogs of natural lipids. VII. Synthesis of cyclopentanoid analogs of phosphatidylcholine.
title_full_unstemmed Analogs of natural lipids. VII. Synthesis of cyclopentanoid analogs of phosphatidylcholine.
title_sort analogs of natural lipids. vii. synthesis of cyclopentanoid analogs of phosphatidylcholine.
publisher Elsevier
series Journal of Lipid Research
issn 0022-2275
publishDate 1982-01-01
description 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.
url http://www.sciencedirect.com/science/article/pii/S0022227520381876
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