Synthesis, structure, and conformation of the dilactone derivative of GD1b ganglioside

G Fronza; G Kirschner; D Acquotti; S Sonnino

doi:10.1016/0008-6215(89)85087-6

Synthesis, structure, and conformation of the dilactone derivative of GD1b ganglioside

Carbohydr Res. 1989 Dec 21;195(1):51-8. doi: 10.1016/0008-6215(89)85087-6.

Authors

G Fronza¹, G Kirschner, D Acquotti, S Sonnino

Affiliation

¹ CNR Study Center for Natural Organic Substances, Department of Chemistry, Polytechnic of Milan, Italy.

PMID: 2636045
DOI: 10.1016/0008-6215(89)85087-6

Abstract

Treatment of DG1b, beta-Gal-(1----3)-beta-GalNAc-(1---- 4)-[alpha-Neu5Ac-(2----8)-alpha-Neu5Ac-(2---- 3)]-beta-Gal-(1----4)-beta-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 -beta-Gal-(1 ----4)-beta-Glc- portion of the ganglioside moiety.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Carbohydrate Conformation
Carbohydrate Sequence
Chromatography, Thin Layer
Colorimetry
Densitometry
Gangliosides* / chemical synthesis
Lactones* / chemical synthesis
Magnetic Resonance Spectroscopy
Molecular Sequence Data

Substances

Gangliosides
Lactones
ganglioside GD1b dilactone