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Flavin-mediated dual oxidation controls an enzymatic Favorskii-type rearrangement

Author

Listed:
  • Robin Teufel

    (Center for Marine Biotechnology and Biomedicine, Scripps Institution of Oceanography, University of California San Diego)

  • Akimasa Miyanaga

    (Center for Marine Biotechnology and Biomedicine, Scripps Institution of Oceanography, University of California San Diego)

  • Quentin Michaudel

    (The Scripps Research Institute, 10550 North Torrey Pines Road, La Jolla, California 92037, USA)

  • Frederick Stull

    (Program in Chemical Biology, University of Michigan)

  • Gordon Louie

    (Howard Hughes Medical Institute, The Salk Institute for Biological Studies, Jack H. Skirball Center for Chemical Biology and Proteomics)

  • Joseph P. Noel

    (Howard Hughes Medical Institute, The Salk Institute for Biological Studies, Jack H. Skirball Center for Chemical Biology and Proteomics)

  • Phil S. Baran

    (The Scripps Research Institute, 10550 North Torrey Pines Road, La Jolla, California 92037, USA)

  • Bruce Palfey

    (Program in Chemical Biology, University of Michigan
    University of Michigan)

  • Bradley S. Moore

    (Center for Marine Biotechnology and Biomedicine, Scripps Institution of Oceanography, University of California San Diego
    Skaggs School of Pharmacy and Pharmaceutical Sciences, University of California San Diego)

Abstract

Structural and functional studies reveal how the bacterial flavoenzyme EncM catalyses the oxygenation–dehydrogenation dual oxidation of a highly reactive substrate, and show that EncM maintains a stable flavin oxygenating species that promotes substrate oxidation and triggers a rarely seen Favorskii-type rearrangement.

Suggested Citation

  • Robin Teufel & Akimasa Miyanaga & Quentin Michaudel & Frederick Stull & Gordon Louie & Joseph P. Noel & Phil S. Baran & Bruce Palfey & Bradley S. Moore, 2013. "Flavin-mediated dual oxidation controls an enzymatic Favorskii-type rearrangement," Nature, Nature, vol. 503(7477), pages 552-556, November.
    • Handle: RePEc:nat:nature:v:503:y:2013:i:7477:d:10.1038_nature12643
    DOI: 10.1038/nature12643
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    Cited by:

    1. Ke-Na Feng & Yue Zhang & Mingfang Zhang & Yan-Long Yang & Ji-Kai Liu & Lifeng Pan & Ying Zeng, 2023. "A flavin-monooxygenase catalyzing oxepinone formation and the complete biosynthesis of vibralactone," Nature Communications, Nature, vol. 14(1), pages 1-13, December.
    2. Qian Wang & Ning Liu & Yaming Deng & Yuze Guan & Hongli Xiao & Tara A. Nitka & Hui Yang & Anju Yadav & Lela Vukovic & Irimpan I. Mathews & Xi Chen & Chu-Young Kim, 2023. "Triepoxide formation by a flavin-dependent monooxygenase in monensin biosynthesis," Nature Communications, Nature, vol. 14(1), pages 1-15, December.

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