HOME HELP FEEDBACK SUBSCRIPTIONS ARCHIVE SEARCH TABLE OF CONTENTS		QUICK SEARCH:   [advanced] Author: Keyword(s): Year:  Vol:  Page:

This Article Full Text (PDF) Alert me when this article is cited Alert me if a correction is posted Services Similar articles in this journal Similar articles in PubMed Alert me to new issues of the journal Download to citation manager Request Permissions Citing Articles Citing Articles via HighWire Citing Articles via Google Scholar Google Scholar Articles by Hanahan, D. J. Articles by Ayer, D. E. Search for Related Content PubMed PubMed Citation Articles by Hanahan, D. J. Articles by Ayer, D. E. Social Bookmarking                      What's this?

Journal of Lipid Research, Vol 26, 1345-1355, Copyright © 1985 by Lipid Research, Inc.

ARTICLES

A novel approach to structure proof of glyceryl ether-containing glycerophospholipids. Base-catalyzed methanolysis of platelet- activating factor (AGEPC) at 60 degrees C

DJ Hanahan, ST Weintraub, SJ Friedberg, A Tokumura and DE Ayer

A novel reaction was explored in which synthetic platelet-activating factor, 1-O-alkyl-2-acetyl-sn-glycero-3-phosphocholine (AGEPC), upon treatment with 1 N NaOH in methanol at 60 degrees C for 20 min, sequentially released the acetyl group, then the choline moiety with concomitant formation of the monomethyl ester of 1-O-alkyl-glycero- phosphoric acid. A mechanism is proposed in which a transient cyclic phosphate intermediate is formed and then attacked by a CH3O moiety to yield a mixture of the sn-2 and sn-3 methyl esters. Proof of structure of the monomethyl ester derivative was achieved through the use of thin- layer chromatography, aluminum oxide chromatography, and examination of the trimethylsilyl derivative of the monomethyl ester by gas-liquid chromatography-mass spectrometry. Replacement of the acyl group on the 2 position with an ethyl or methyl residue completely prevented any attack by 1 N NaOH in methanol at 60 degrees C. Sphingomyelin was not attacked and only acetate removal was noted with 1-O-alkyl-2-acetyl-sn- glycero-3-phosphoethanolamine under similar conditions. The significance of these findings as they relate to the influence of substituents on the chemical and biological reactivity of AGEPC is discussed.
CiteULike    Complore    Connotea    Del.icio.us    Digg    Reddit    Technorati    What's this?

This article has been cited by other articles:

				T. M. McIntyre, A. V. Pontsler, A. R. Silva, A. St. Hilaire, Y. Xu, J. C. Hinshaw, G. A. Zimmerman, K. Hama, J. Aoki, H. Arai, et al. From the Cover: Identification of an intracellular receptor for lysophosphatidic acid (LPA): LPA is a transcellular PPARgamma agonist PNAS, January 7, 2003; 100(1): 131 - 136. [Abstract] [Full Text] [PDF]

				K. Liliom, D. J. Fischer, T. Virag, G. Sun, D. D. Miller, J.-L. Tseng, D. M. Desiderio, M. C. Seidel, J. R. Erickson, and G. Tigyi Identification of a Novel Growth Factor-like Lipid, 1-O-cis-Alk-1'-enyl-2-lyso-sn-glycero-3-phosphate (Alkenyl-GP) That Is Present in Commercial Sphingolipid Preparations J. Biol. Chem., May 29, 1998; 273(22): 13461 - 13468. [Abstract] [Full Text] [PDF]