A simple procedure is described for preparing lyso-GM1, a GM1 derivative that lacks the fatty acid moiety, starting from GM1 ganglioside using a one-pot reaction. Ganglioside deacylation was carried out in KOH/propan-1-ol in the absence of oxygen. The yield of lyso-GM1 under optimal conditions (6 h, 90-degrees-C, 0.2 N KOH, 1 mm GM1) was 54%. The chemical structure of lyso-GM1 was determined by H-1-NMR and FAB-MS analyses, thus proving that the acetamide groups of galactosamine and sialic acid units were not affected during the deacylation reaction.
PREPARATION OF LYSO-GM1 (II(3)NEU5ACGGOSE(4)-LONG CHAIN BASES) BY A ONE-POT REACTION / S. SONNINO, D. ACQUOTTI, G. KIRSCHNER, A. UGUAGLIANZA, L. ZECCA, F. RUBINO, G. TETTAMANTI. - In: JOURNAL OF LIPID RESEARCH. - ISSN 0022-2275. - 33:8(1992), pp. 1221-1226.
PREPARATION OF LYSO-GM1 (II(3)NEU5ACGGOSE(4)-LONG CHAIN BASES) BY A ONE-POT REACTION
S. SONNINO;F. RUBINO;G. TETTAMANTI
1992
Abstract
A simple procedure is described for preparing lyso-GM1, a GM1 derivative that lacks the fatty acid moiety, starting from GM1 ganglioside using a one-pot reaction. Ganglioside deacylation was carried out in KOH/propan-1-ol in the absence of oxygen. The yield of lyso-GM1 under optimal conditions (6 h, 90-degrees-C, 0.2 N KOH, 1 mm GM1) was 54%. The chemical structure of lyso-GM1 was determined by H-1-NMR and FAB-MS analyses, thus proving that the acetamide groups of galactosamine and sialic acid units were not affected during the deacylation reaction.
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