A Glutathione Conjugate of 2, 4-Dichloro-1-nitrobenzene: Its Detection as a Metabolic Intermediate and Further Metabolism in <i>Mucor javanicus</i>

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  • TAHARA Satoshi
    Department of Agricultural Chemistry, Faculty of Agriculture, Hokkaido University
  • HAFSAH Zainuddin
    Department of Agricultural Chemistry, Faculty of Agriculture, Hokkaido University Present address: Hasanuddin University
  • MIZUTANI Junya
    Department of Agricultural Chemistry, Faculty of Agriculture, Hokkaido University

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Other Title
  • 2,4-ジクロロ-1-ニトロベンゼンのゲルタチオン抱合体: <i>Mucor javanicus</i> における中間代謝物としての検出およびその代謝
  • 2,4-ジクロロー1-ニトロベンゼンのグルタチオン抱合体--Mucor javanicusにおける中間代謝物としての検出およびその代謝〔英文〕
  • 2 4 ジクロロ 1 ニトロベンゼン ノ グルタチオン ホウゴウタイ Muco
  • Microbial Metabolism of Chlorinated Nitrobenzenes (Part 3)

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Abstract

Formation of a 2, 4-dichloro-1-nitrobenzene glutathione conjugate [S-(5-chloro-2-nitrophenyl) glutathione, 2] was confirmed in the cell-free system of Mucor javanicus which metabolizes 2, 3- and 2, 4-dichloro-1-nitrobenzenes into the corresponding chloro-methylthio-nitrobenzenes or chloro-methylthiobenzenamines. Further metabolisms of 2, the corresponding cysteine conjugate (3) and 5-chloro-2-nitrobenzenethiol (4) were investigated. Oxidation products (S-oxides and S-dioxides) of the formerly identified methylthio-containing metabolites were isolated from the growing cultures of the fungus administered 2. S-(5-Chloro-2-nitrophenyl) cysteine (3) and N-acetyl-S-(5-chloro-2-nitrophenyl) cysteine (7) were newly identified as metabolites of 2 in the resting cell system of the fungus.

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