Synthesis of ganglioside GM3 and GM4 analogs having mimics of ceramide moieties and their binding activities with influenza virus A.
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.
Nagao
Y
Y
School of Pharmaceutical Sciences, University of Shizuoka, Japan.
Nekado
T
T
Ikeda
K
K
Achiwa
K
K
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
D005679:G(M3) Ganglioside; D005732:Gangliosides; C028253:ganglioside, GM4