A total synthesis of the methyl glycoside of ganglioside GM(1).
The total synthesis of the methyl glycoside of GM(1) (1b) has been accomplished. The key step in the synthesis involves the sulfonamidoglycosidation reaction, which is used to create a beta-linkage leading to a GalNAc residue joined to the C4 hydroxyl group of a galactose unit of a C3 sialylated lactosyl moiety. The "proximal hydroxyl" directing effect, which has been postulated before, manifests in this context as well leading to the preponderant formation of the beta-glycoside. Together with asialo GM(1) and other substructures, the GM(1) methyl glycoside has been submitted for biological assays as potential ligands for bacterial and viral infection sites.
Bhattacharya
S K
SK
Department of Chemistry, Columbia University, Havemeyer Hall, New York, New York 10027, USA.
Danishefsky
S J
SJ
D002236:Carbohydrate Conformation; D002240:Carbohydrate Sequence; D005677:G(M1) Ganglioside / Q000737:chemistry*; D006027:Glycosides / Q000138:chemical synthesis*; D009682:Magnetic Resonance Spectroscopy; D008969:Molecular Sequence Data; D016339:Spectrometry, Mass, Fast Atom Bombardment
D006027:Glycosides; D005677:G(M1) Ganglioside