Lactonization of GD1b ganglioside under acidic conditions

R Bassi; L Riboni; S Sonnino; G Tettamanti

doi:10.1016/0008-6215(89)85113-4

Lactonization of GD1b ganglioside under acidic conditions

Carbohydr Res. 1989 Oct 31:193:141-6. doi: 10.1016/0008-6215(89)85113-4.

Authors

R Bassi¹, L Riboni, S Sonnino, G Tettamanti

Affiliation

¹ Department of Medical Chemistry and Biochemistry, Medical School, University of Milan, Italy.

PMID: 2611779
DOI: 10.1016/0008-6215(89)85113-4

Abstract

Gangliosides that contain the disialosyl residue alpha-Neu5Ac-(2--8)-alpha-Neu5Ac-(2--3)- can lactonize in the presence of traces of acid and this reaction has been studied in detail on GD1b [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]. Lactonization occurs rapidly at a proton-ganglioside molar ratio of less than 1. At equilibrium, the ratio of GD1b to its lactone is 3:7. The data suggest the possibility that a proton-driven lactonization of gangliosides may occur in vivo.

Publication types

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

MeSH terms

Animals
Brain Chemistry
Cattle
Chromatography, Thin Layer
Gangliosides / metabolism*
Hydrogen-Ion Concentration
Lactones / metabolism*
Oxidation-Reduction

Substances

Gangliosides
Lactones
ganglioside, GD1b
ganglioside, GD1b-lactone