Coupling Reaction of Indolepyruvic Acid by StaD and Its Product: Implications for Biosynthesis of Indolocarbazole and Violacein

Authors

  • Dr. Shumpei Asamizu,

    1. Department of Biotechnology, Faculty of Engineering, Toyama Prefectural University, Toyama 939-0398 (Japan)
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    • These authors contributed equally to this work.

  • Dr. Satoshi Hirano,

    1. RIKEN SPring-8 Center, 1-1-1 Koto, Sayo, Hyogo 679-5148 (Japan)
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    • These authors contributed equally to this work.

  • Prof. Hiroyasu Onaka,

    Corresponding author
    1. Department of Biotechnology, Faculty of Engineering, Toyama Prefectural University, Toyama 939-0398 (Japan)
    2. Present address: Department of Biotechnology, Graduate School of Agricultural and Life Sciences, The University of Tokyo, 1-1-1 Yayoi, Bunkyo, Tokyo 113-8657 (Japan)
    • Department of Biotechnology, Faculty of Engineering, Toyama Prefectural University, Toyama 939-0398 (Japan)
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  • Dr. Hiroyuki Koshino,

    1. Chemical Biology Department, RIKEN Advanced Science Institute, 2-1 Hirosawa, Wako, 351-0198 (Japan)
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  • Dr. Yoshitsugu Shiro,

    1. RIKEN SPring-8 Center, 1-1-1 Koto, Sayo, Hyogo 679-5148 (Japan)
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  • Prof. Shingo Nagano

    Corresponding author
    1. Department of Chemistry and Biotechnology, Graduate School of Engineering, Tottori University, 4-101 Koyama-cho minani, Tottori 680-8552 (Japan)
    • Department of Chemistry and Biotechnology, Graduate School of Engineering, Tottori University, 4-101 Koyama-cho minani, Tottori 680-8552 (Japan)
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Abstract

original image

Central C[BOND]C coupling: It has been proposed that the heme-containing enzyme StaD and its homologues catalyze a coupling reaction that yields an indolepyruvic acid (IPA) imine in indolocarbazole biosynthesis. We show that StaD uses IPA enol as an analogue of natural substrate to produce an IPA dimer, in the first direct evidence of the C[BOND]C coupling dimerization reaction catalyzed by StaD.

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