Synthesis of Ganglioside G_<M3> and G_<M4> Analogs Having Mimics of Ceramide Moieties and Their Binding Activities with Influenza Virus A

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概要

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• 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.

• 公益社団法人日本薬学会の論文
• 1995-09-15

著者

• 阿知波 一雄

  静岡県立大学薬学部

• 阿知波 一雄

  School of Pharmaceutical Sciences, University of Shizuoka

• 阿知波 一雄

  静岡県大薬

• 阿知波 一雄

  東大・薬

• 池田 潔

  School Of Pharmaceutical Sciences University Of Shizuoka

• 池田 潔

  Tanabe Seiyaku Co. Ltd. Saitama Jpn

• 長尾 美宏

  School of Pharmaceutical Sciences, University of Shizuoka

• 根門 孝裕

  School of Pharmaceutical Sciences, University of Shizuoka

• Achiwa Kazuo

  School Of Pharmaceutical Sciences(laboratory Of Medicinal Chemistry)

• 池田 かおり

  Developmental Research Laboratories Shionogi & Co. Ltd.

• 根門 孝裕

  School Of Pharmaceutical Sciences University Of Shizuoka

• 長尾 美宏

  School Of Pharmaceutical Sciences University Of Shizuoka

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