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  [in Japanese] Novel Metabolic Pathway of Phenols Catalyzed by Cytochrome P450 and Its Mechanism  [in Japanese]

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Abstract

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.

Journal

  • Journal of Synthetic Organic Chemistry, Japan

    Journal of Synthetic Organic Chemistry, Japan 58(12), 1202-1209, 2000-12-01

    The Society of Synthetic Organic Chemistry, Japan

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Codes

  • NII Article ID (NAID)
    10008824723
  • NII NACSIS-CAT ID (NCID)
    AN0024521X
  • Text Lang
    JPN
  • Article Type
    OTR
  • ISSN
    00379980
  • NDL Article ID
    5594744
  • NDL Source Classification
    ZP11(科学技術--化学・化学工業--有機化学・有機化学工業)
  • NDL Call No.
    Z17-256
  • Data Source
    CJP  NDL  J-STAGE 
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