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-0-acetyl-3, 5-dideoxy-2-thio-ß-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. © 1995, The Pharmaceutical Society of Japan. All rights reserved.