Chemical and Pharmaceutical Bulletin p. 1536 - 1542 (1995)
Update date:2022-08-02
Topics: Synthesis NMR (nuclear magnetic resonance) Ganglioside G(M3) and G(M4) analogs Ceramide Binding activities Influenza virus A Binding assay HPLC (High Performance Liquid Chromatography)
Nagao
Nekado
Ikeda
Achiwa
Ganglioside G(M4) (1) and G(M3) (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-β-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.
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