Treatment of GD1b, β-Gal-(1→3)-β-GalNAc-(1→4)-[α-Neu5Ac-(2→8 )-α-Neu5Ac-(2→3)]-β-Gal-(1→4)-β-Glc-(1→1) -Cer, with dicyclohexylcarbodi-imide in anhydrous methyl sulfoxide affords 95-98% of GD1b-dilactone. The carboxyl groups of the two sialic acid units are involved in ester linkages, as proved by ammoniolysis and reduction which gave derivatives containing the amide of sialic acid and N-acetylneuraminulose, respectively. 1H-N.m.r. spectroscopy showed that the lactone rings involved position 9 of the inner sialic acid and position 2 of the inner galactose and that the disialosyl chain is extended toward the -β-Gal-(1→4)-β-Glc- portion of the ganglioside moiety.

SYNTHESIS, STRUCTURE, AND CONFORMATION OF THE DILACTONE DERIVATIVE OF GD1B GANGLIOSIDE / G. FRONZA, G. KIRSCHNER, D. ACQUOTTI, S. SONNINO. - In: CARBOHYDRATE RESEARCH. - ISSN 0008-6215. - 195:1(1989), pp. 51-58.

SYNTHESIS, STRUCTURE, AND CONFORMATION OF THE DILACTONE DERIVATIVE OF GD1B GANGLIOSIDE

S. SONNINO
Ultimo
1989

Abstract

Treatment of GD1b, β-Gal-(1→3)-β-GalNAc-(1→4)-[α-Neu5Ac-(2→8 )-α-Neu5Ac-(2→3)]-β-Gal-(1→4)-β-Glc-(1→1) -Cer, with dicyclohexylcarbodi-imide in anhydrous methyl sulfoxide affords 95-98% of GD1b-dilactone. The carboxyl groups of the two sialic acid units are involved in ester linkages, as proved by ammoniolysis and reduction which gave derivatives containing the amide of sialic acid and N-acetylneuraminulose, respectively. 1H-N.m.r. spectroscopy showed that the lactone rings involved position 9 of the inner sialic acid and position 2 of the inner galactose and that the disialosyl chain is extended toward the -β-Gal-(1→4)-β-Glc- portion of the ganglioside moiety.
Settore BIO/10 - Biochimica
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Utilizza questo identificativo per citare o creare un link a questo documento: http://hdl.handle.net/2434/187840
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