title: A total synthesis of the methyl glycoside of ganglioside GM(1).
abstract: 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.
authors.affiliation: Department of Chemistry, Columbia University, Havemeyer Hall, New York, New York 10027, USA.
authors.forename: S K
authors.initials: SK
authors.lastname: Bhattacharya
authors.forename: S J
authors.initials: SJ
authors.lastname: Danishefsky
mesh_terms: 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
chemical_list: D006027:Glycosides; D005677:G(M1) Ganglioside