書誌事項
- タイトル別名
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- Synthesis of Tryptophan Metabolites by Biomimetic Reactions
- セイタイナイ ルイジ ハンノウ ニ ヨル トリプトファン タイシャ サンブツ
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抄録
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.
収録刊行物
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- 薬学雑誌
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薬学雑誌 106 (11), 964-981, 1986
公益社団法人 日本薬学会
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詳細情報 詳細情報について
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- CRID
- 1390282681130683392
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- NII論文ID
- 110003648557
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- NII書誌ID
- AN00284903
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- ISSN
- 13475231
- 00316903
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- NDL書誌ID
- 3124454
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- データソース種別
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- JaLC
- NDL
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