生体内類似反応によるトリプトファン代謝産物の合成研究

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概要

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• Biomimetic synthesis of tryptophan metabolites and some indole alkaloids from tryptophan are summarized. Dye-sensitized photooxygenation of tryptophan gave 3a-hydroperoxy-pyrroloindole (12) in aqueous solution, formylkynurenine in acetic acid-sodium carbonate buffer (pH 7) and 5-hydroxy-formylkynurenine (16) in phosphate buffer (pH 8). On the other hand, dye-sensitized photooxygenation in formic acid or Tl (III) oxidation of tryptamine (21) and the diketopiperazine (25) gave oxidative dimers which furnished (±) folicanthine on reduction and (-)-ditryptophenaline. The dye-sensitized photooxygenation of the indoloquinolizidine (29) gave 2-acylindole (30). Cyclic tautomers of tryptophans (40,42,44) obtained by dissolving tryptophans in phosphoric acid have been shown to be a useful intermediate to prepare 5-halo, 5-nitro, 5-hydroxy, 5-methoxy, and 6-methoxytryptophans (47,50,52,55) by the electrophilic substitution or oxidation with lead tetraacetate in trifluoroacetic acid. Biomimetic synthesis of tryptoquivalines, tremorgic micotoxins, from D- and L-tryptophans using oxidative double cyclization of the indole-3-propionic acids (79,90) as key steps have been discussed.

• 社団法人日本薬学会の論文
• 1986-11-25

著者

• 日野 亨

  千葉大 薬

• 日野 亨

  千葉大学薬学部

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