title: Synthesis of ganglioside GM3 and GM4 analogs having mimics of ceramide moieties and their binding activities with influenza virus A.
abstract: Ganglioside GM4 (1) and GM3 (2) analogs, which contain mimics of the ceramide moieties of gangliosides, were synthesized. The syntheses of 1 and 2 feature stereoselective glycosylation of methyl (phenyl 5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-2-thio-beta-D- galacto-2-nonulopyranosid)onate (10) as the sialosyl donor with suitably protected galactose and lactose acceptors catalyzed by N-bromosuccinimide (NBS), iodine, and tetrabutylammonium trifluoromethanesulfonate (TBAOTf) as the glycosyl promoter in acetonitrile under kinetically controlled conditions. Compound 2 exhibited binding activity towards influenza virus A.
authors.affiliation: School of Pharmaceutical Sciences, University of Shizuoka, Japan.
authors.forename: Y
authors.initials: Y
authors.lastname: Nagao
authors.forename: T
authors.initials: T
authors.lastname: Nekado
authors.forename: K
authors.initials: K
authors.lastname: Ikeda
authors.forename: K
authors.initials: K
authors.lastname: Achiwa
mesh_terms: D005679:G(M3) Ganglioside / Q000031:analogs & derivatives* / Q000378:metabolism*; D005732:Gangliosides / Q000378:metabolism*; D009980:Influenza A virus / Q000378:metabolism*; D009682:Magnetic Resonance Spectroscopy; D016339:Spectrometry, Mass, Fast Atom Bombardment; D013055:Spectrophotometry, Infrared
chemical_list: D005679:G(M3) Ganglioside; D005732:Gangliosides; C028253:ganglioside, GM4