Synthesis of Ganglioside G_M3 and G_M4 Analogs Having Mimics of Ceramide Moieties and Their Binding Activities with Influenza Virus A

Abstract

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 trifluotomethanesulfonate (TBAOTf) as the glycosyl promoter in acetonitrile under kineticaly controlled conditions. Compound 2 exhibited binding activity towards influenza virus A.