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J. Lipid Res.
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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

Oscar Valientea, Laura Maurib, Riccardo Casellatob, Luis E. Fernandeza, and Sandro Sonninob
a Vaccines Department, Center of Molecular Immunology, Havana 11600, Cuba
b Study Center for the Functional Biochemistry of Brain Lipids, Department of Medical Chemistry and Biochemistry-LITA, Medical School of the University of Milan, 20090 Segrate (Milan), Italy

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