Enzymatic synthesis of new pyridine nucleosides. Clitidine and its amide derivative.

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概要

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• Two β-NAD-analogs were prepared utilizing a base-exchange reaction catalyzed by pig-brain NADase. These analogs were proved to contain a methyl 1,4-dihydro-4-iminonicotinate and a 1,4-dihydro-4-iminonicotinamide moiety. By successive hydrolytic degradations of these analogs, 1,4-dihydro-4-iminopyridine β-ribosides with 3-carboxyl and 3-carbamoyl groups were prepared in good yields. The former compound was identical with clitidine, a toxic pyridine nucleoside recently isolated from a toadstool. The present synthesis confirmed the 1,4-dihydro-4-imino β-riboside structure of clitidine. Preliminary biological tests showed that the 3-carbamoyl compound was more toxic than clitidine, suggesting that the amide derivative of clitidine is an essential toxic substance in the toadstool.

• 公益社団法人 日本化学会の論文

著者

• Shirahama Haruhisa

  Department Of Chemistry Faculty Of Science Hokkaido University

• Matsumoto Takeshi

  Department Of Biology Faculty Of Science Kumamoto University

• Tono-oka Shuichi

  Institute of Immunological Science, Hokkaido University

• Sasahara Yasuhiko

  Institute of Immunological Science, Hokkaido University

• Sasaki Akio

  Institute of Immunological Science, Hokkaido University

• Kakimoto Shichiro

  Institute of Immunological Science, Hokkaido University

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