Journal of Lipid Research, Vol 33, 1079-1084, Copyright © 1992 by Lipid Research, Inc.

ARTICLES

Improved preparation method for lysogangliosides

S Gasa, K Kamio and A Makita
Biochemistry Laboratory, Hokkaido University School of Medicine, Sapporo, Japan.

Lyso-GM3 and -GM1 gangliosides were prepared from the corresponding N,N'-dideacylated gangliosides using N-trifluoroacetylation at the sphingosine moiety, followed by N-acetylation and mild saponification. The blocking reaction was performed using a water-ether bilayer system at alkaline medium, in which the N-trifluoroacetylation occurred predominantly at the lipid moiety. Through the procedure, lysoGM3 and lysoGM1 were obtained with higher yields from the corresponding dideacylated gangliosides than through the previous method using 9- fluorenylmethoxycarbonyl chloride as a blocking group or of direct N- acetylation of it on liposomes containing starting ganglioside and other lipid. Chemical structures of the lysogangliosides and the synthetic intermediates were confirmed by the proton nuclear magnetic resonance spectrometry and negative fast atom bombardment-mass spectrometry.
CiteULike    Complore    Connotea    Del.icio.us    Digg    Reddit    Technorati    What's this?

This article has been cited by other articles:

				O. Valiente, L. Mauri, R. Casellato, L. E. Fernandez, and S. Sonnino Preparation of deacetyl-, lyso-, and deacetyl-lyso-GM3 by selective alkaline hydrolysis of GM3 ganglioside J. Lipid Res., August 1, 2001; 42(8): 1318 - 1324. [Abstract] [Full Text] [PDF]