シトクロムP450によるフェノール類新規代謝反応の検索と機構解析 Novel Metabolic Pathway of Phenols Catalyzed by Cytochrome P450 and Its Mechanism

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We have found a novel metabolic pathway of phenols catalyzed by cytochrome P450 and its chemical models. When various <I>p</I>-substituted phenols (substituent = OPh, NO<SUB>2</SUB>, CN, CH<SUB>2</SUB>OH, COCH<SUB>3</SUB>, COPh, COOH, F, Cl, and Br) were reacted with rat liver microsomes system or <I>meso</I>-tetraphenylporphinatoiron (III) chloride model system, the substituent was eliminated to produce hydroquinone. In the case of <I>p</I>-cresol, <I>p</I>-toluquinol was formed instead of hydroquinone. To elucidate how the substituent is eliminated, we attempted to detect the product derived from the eliminated group. Results indicated that the mechanism of this reaction can be divided into two types : the substituent is eliminated as an anion and as a cation. P450 also catalyzed phenol coupling reaction to give biphenyl derivatives, diphenyl ether derivatives, and dibenzodioxin.

収録刊行物

  • 有機合成化学協会誌

    有機合成化学協会誌 58(12), 1202-1209, 2000-12-01

    The Society of Synthetic Organic Chemistry, Japan

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各種コード

  • NII論文ID(NAID)
    10008824723
  • NII書誌ID(NCID)
    AN0024521X
  • 本文言語コード
    JPN
  • 資料種別
    OTR
  • ISSN
    00379980
  • NDL 記事登録ID
    5594744
  • NDL 雑誌分類
    ZP11(科学技術--化学・化学工業--有機化学・有機化学工業)
  • NDL 請求記号
    Z17-256
  • データ提供元
    CJP書誌  NDL  J-STAGE 
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