Chemical and Pharmaceutical Bulletin
Online ISSN : 1347-5223
Print ISSN : 0009-2363
ISSN-L : 0009-2363
Synthesis of Ganglioside GM3 and GM4 Analogs Having Mimics of Ceramide Moieties and Their Binding Activities with Influenza Virus A
Yoshihiro NAGAOTakahiro NEKADOKiyoshi IKEDAKazuo ACHIWA
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JOURNAL FREE ACCESS

1995 Volume 43 Issue 9 Pages 1536-1542

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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-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.

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© The Pharmaceutical Society of Japan
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