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标题：Preparation of deacetyl-, lyso-, and deacetyl-lyso-GM3 by selective alkaline hydrolysis of GM3 ganglioside
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作者：Oscar Valiente ; Laura Mauri ; Riccardo Casellato 等
期刊名称：JLR Papers In Press
印刷版ISSN：0022-2275
电子版ISSN：1539-7262
出版年度：2001
卷号：42
期号：8
页码：1318-1324
语种：English
出版社：American Society for Biochemistry and Molecular Biology
摘要：Three methods (using GM₃ quantities ranging from a few milligrams to grams) have been developed to prepare, in high yield, the three derivatives of ganglioside GM₃ [α-Neu5Ac-(2-3)-β-Gal-(1-4)-β-Glc-(1-1)-ceramide]: deacetyl-GM₃ [α-Neu-(2-3)-β-Gal-(1-4)-β-Glc-(1-1)-ceramide], lyso-GM₃ [α-Neu5Ac-(2-3)-β-Gal-(1-4)-β-Glc-(1-1)-sphingosine], and deacetyl-lyso-GM₃ [α-Neu-(2-3)-β-Gal-(1-4)-β-Glc-(1-1)-sphingosine]. This is the first report of the preparation of lyso-GM₃ by a one-pot reaction. We can now define the optimal conditions for the different preparations. Preparation of deacetyl-GM₃: alkaline reagent, 2 M KOH in water; GM₃ concentration, 33 mg/ml; reaction temperature, 90 °C; reaction time, 3.5 h; nitrogen atmosphere. Preparation of deacetyl-lyso-GM₃: alkaline reagent, 8 M KOH in water; GM₃ concentration, 10 mg/ml; reaction temperature, 90 °C; reaction time, 18 h; nitrogen atmosphere. Preparation of lyso-GM₃: alkaline reagent, 1 M sodium tert- butoxide in methanol; GM₃ concentration, 10 mg/ml; reaction temperature, 80 °C; reaction time, 18 h; anhydrous conditions. The percentage yield of deacetyl-GM₃ was 70–75%, that of deacetyl-lyso-GM₃ 100%, and of lyso-GM₃ 36–40%. Deacetyl-GM₃, deacetyl-lyso-GM₃, and lyso-GM₃ were purified by column chromatography, and chemical structures were confirmed by electron spray-mass spectrometry. —Valiente, O., 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. 2001. 42: 1318–1324.
关键词：TLC staining ; tritium ; tert -butoxide ; ESI-MS