CHEMICAL SYNTHESIS OF C-13-LABELED GANGLIOSIDE GB(3) TRISACCHARIDE FROM [U-C-13]-D-GLUCOSE

The interaction of bacterial toxins with their cell surface glycolipid receptors offers scope for therapeutic intervention. Whilst crystal a nd solution structures of Escherichia coli verotoxin-1 have been repor ted, the precise nature of the interaction of the glycolipid binding d omain of the toxin with its natural ligand, ganglioside Gb(3) (Gal alp ha 1-->4Gal beta 1-->4Glc beta 1-->Cer), remain to be confirmed. To th is end we now report the synthesis of the (2-trimethylsilyl)ethyl glyc oside of the Gb(3) trisaccharide in isotopically enriched form from [U -C-13]-D-glucose. (C) 1998 Elsevier Science Ltd. All rights reserved.