| Synthesis of conformationally restricted acidic lipids. I. Cyclopentanoid analogs of phosphatidylserine. | |
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MedLine Citation:
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PMID: 6875388 Owner: NLM Status: MEDLINE |
Abstract/OtherAbstract:
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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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Authors:
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H Pajouhesh; A J Hancock |
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Publication Detail:
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Type: Comparative Study; Journal Article; Research Support, Non-U.S. Gov't; Research Support, U.S. Gov't, P.H.S. |
Journal Detail:
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Title: Journal of lipid research Volume: 24 ISSN: 0022-2275 ISO Abbreviation: J. Lipid Res. Publication Date: 1983 May |
Date Detail:
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Created Date: 1983-09-09 Completed Date: 1983-09-09 Revised Date: 2008-11-21 |
Medline Journal Info:
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Nlm Unique ID: 0376606 Medline TA: J Lipid Res Country: UNITED STATES |
Other Details:
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Languages: eng Pagination: 645-51 Citation Subset: IM |
Export Citation:
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APA/MLA Format Download EndNote Download BibTex |
| MeSH Terms | |
Descriptor/Qualifier:
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Chromatography, Thin Layer Cyclopentanes / chemical synthesis* Diazomethane Hot Temperature Molecular Conformation Optical Rotation Phosphatidylserines / chemical synthesis* Spectrophotometry, Infrared Stereoisomerism |
| Grant Support | |
ID/Acronym/Agency:
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GM-21047-06/GM/NIGMS NIH HHS |
| Chemical | |
Reg. No./Substance:
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0/Cyclopentanes; 0/Phosphatidylserines; 334-88-3/Diazomethane |
From MEDLINE®/PubMed®, a database of the U.S. National Library of Medicine
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