Three methods (using GM(3) quantities ranging from a few milligrams to grams) have been developed to prepare, in high yield, the three derivatives of ganglioside GM(3) [alpha -Neu5A-c(2-3)-beta -Gal-(1-4)-beta -Glc-(1-1)-ceramide]: deacetyl-GM(3) [alpha -Neu-(2-3)-beta -Gal-(1-4)-beta -Glc-(1-1)-ceramide], lyso-GM(3) [alpha -Neu5Ac-(2-3)-beta -Gal-(1-4)-beta -Glc-(1-1)-sphingosine], and deacetyl-lyso-GM(3) [alpha -Neu-(2-3)-beta -Gal-(1-4)-beta -Glc-(1-1)-sphingosine]. This is the first report of the preparation of lyso-GM(3) by a one-pot reaction. We can now define the optimal conditions for the different preparations. Preparation of deacetyl-GM(3): alkaline reagent, 2 M KOH in water; GM(3) concentration, 33 mg/nl; reaction temperature, 90 degreesC; reaction time, 3.5 h; nitrogen atmosphere. Preparation of deacetyl-lyso-GM(3): alkaline reagent, 8 M KOH in water; GM(3) concentration, 10 mg/ml; reaction temperature, 90 degreesC; reaction time, 18 h; nitrogen atmosphere. Preparation of lyso-GM(3): alkaline reagent, 1 M sodium tertbutoxide in methanol; GM(3) concentration, 10 mg/ml; reaction temperature, 80 degreesC; reaction time, 18 h; anhydrous conditions. The percentage yield of deacetyl-GM(3) was 70-75%, that of deacetyl-lyso-GM(3) 100%, and of lyso-GM(3) 36-40%. 12 Deacetyl-GM(3), deacetyl-lyso-GM(3), and lyso-GM(3) were purified by column chromatography, and chemical structures were confirmed by electron spray-mass spectrometry.

Preparation of deacetyl-, lyso-, and deacetyl-lyso-GM(3) by selective alkaline hydrolysis of GM(3) ganglioside / O. Valiente, L. Mauri, R. Casellato, L. Fernandez, S. Sonnino. - In: JOURNAL OF LIPID RESEARCH. - ISSN 0022-2275. - 42:8(2001), pp. 1318-1324.

Preparation of deacetyl-, lyso-, and deacetyl-lyso-GM(3) by selective alkaline hydrolysis of GM(3) ganglioside

L. Mauri
Secondo
;
R. Casellato;S. Sonnino
Ultimo
2001

Abstract

Three methods (using GM(3) quantities ranging from a few milligrams to grams) have been developed to prepare, in high yield, the three derivatives of ganglioside GM(3) [alpha -Neu5A-c(2-3)-beta -Gal-(1-4)-beta -Glc-(1-1)-ceramide]: deacetyl-GM(3) [alpha -Neu-(2-3)-beta -Gal-(1-4)-beta -Glc-(1-1)-ceramide], lyso-GM(3) [alpha -Neu5Ac-(2-3)-beta -Gal-(1-4)-beta -Glc-(1-1)-sphingosine], and deacetyl-lyso-GM(3) [alpha -Neu-(2-3)-beta -Gal-(1-4)-beta -Glc-(1-1)-sphingosine]. This is the first report of the preparation of lyso-GM(3) by a one-pot reaction. We can now define the optimal conditions for the different preparations. Preparation of deacetyl-GM(3): alkaline reagent, 2 M KOH in water; GM(3) concentration, 33 mg/nl; reaction temperature, 90 degreesC; reaction time, 3.5 h; nitrogen atmosphere. Preparation of deacetyl-lyso-GM(3): alkaline reagent, 8 M KOH in water; GM(3) concentration, 10 mg/ml; reaction temperature, 90 degreesC; reaction time, 18 h; nitrogen atmosphere. Preparation of lyso-GM(3): alkaline reagent, 1 M sodium tertbutoxide in methanol; GM(3) concentration, 10 mg/ml; reaction temperature, 80 degreesC; reaction time, 18 h; anhydrous conditions. The percentage yield of deacetyl-GM(3) was 70-75%, that of deacetyl-lyso-GM(3) 100%, and of lyso-GM(3) 36-40%. 12 Deacetyl-GM(3), deacetyl-lyso-GM(3), and lyso-GM(3) were purified by column chromatography, and chemical structures were confirmed by electron spray-mass spectrometry.
ESI-MS; tert-butoxide; TLC staining; Tritium
Settore BIO/10 - Biochimica
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Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/2434/189373
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