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Journal of Lipid Research, Vol. 42, 1318-1324, August 2001
Copyright © 2001 by Lipid Research, Inc.

Methods

Preparation of deacetyl-, lyso-, and deacetyl-lyso-GM₃ by selective alkaline hydrolysis of GM₃ ganglioside

Correspondence to: Sandro Sonnino, To whom correspondence should be addressed., Sandro.Sonnino{at}unimi.it (E-mail)

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 [-Neu5Ac-(2-3)-ß-Gal-(1-4)-ß-Glc-(1-1)-ceramide]: deacetyl-GM₃ [-Neu-(2-3)-ß-Gal-(1-4)-ß-Glc-(1-1)-ceramide], lyso-GM₃ [-Neu5Ac-(2-3)-ß-Gal-(1-4)-ß-Glc-(1-1)-sphingosine], and deacetyl-lyso-GM₃ [-Neu-(2-3)-ß-Gal-(1-4)-ß-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.

Supplementary key words: TLC staining, tritium, tert-butoxide, ESI-MS

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