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 Citing Articles Citing Articles via HighWire Citing Articles via Google Scholar Google Scholar Articles by Tsuchihashi, K. Articles by Gasa, S. Search for Related Content PubMed PubMed Citation Articles by Tsuchihashi, K. Articles by Gasa, S. Social Bookmarking                      What's this?

Journal of Lipid Research, Vol 37, 2136-2144, Copyright © 1996 by Lipid Research, Inc.

ARTICLES

Synthesis of a glioma-related ganglioside, O-Ac GM3 having 3-O-Ac ceramide and its substrate property toward hydrolases

K Tsuchihashi, T Daino, T Akino and S Gasa
Department of Chemistry, School of Medicine, Sapporo Medical University, Japan.

An O-acetyl group was selectively introduced into the ceramide moiety at the C-3-O on ganglioside GM3 containing N-acetyl neuraminic acid, the product of which has been previously found in rat glioma tissue as a glioma-associated ganglioside. The introduction of the acetyl residue involved a two-step process involving per O-acetylation of GM3 and saponification with a mild alkaline solution in a bilayer system constituted of water and water-immiscible organic solvent. Of the several solvents studied, 2-pentanol and diethyl ether gave the highest yields (68% and 62%, respectively). The chemical structure of the synthesized 3-O-acetyl GM3 was confirmed by proton nuclear magnetic resonance spectroscopy and fast atom bombardment-mass spectrometry, as well as by comparing the mobilities on thin-layer chromatography of its exoglycosidase-digested products with those of the synthesized, authentic 3-O-acetyl-lactosylceramide and ceramide. Furthermore, the substrate specificities of both 3-O-acetyl GM3 and 3-O-acetyl sphingomyelin toward exo- and endo-hydrolases were examined, revealing that they were hardly cleaved by the endoglycoceramidase and sphingolipid N-deacylase for the 3-O-acetyl GM3 and by sphingomyelinase for 3-O-acetyl sphingomyelin. Thus, the enzymes were found to recognize a free C-3 hydroxyl group on ceramide.
CiteULike    Complore    Connotea    Del.icio.us    Digg    Reddit    Technorati    What's this?

This article has been cited by other articles:

				S. Dasgupta, S. B. Levery, and E. L. Hogan 3-O-acetyl-sphingosine-series myelin glycolipids: characterization of novel 3-O-acetyl-sphingosine galactosylceramide J. Lipid Res., May 1, 2002; 43(5): 751 - 761. [Abstract] [Full Text] [PDF]