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

Robin Teufel, Akimasa Miyanaga, Quentin Michaudel, Frederick Stull, Gordon Louie, Joseph P. Noel, Phil S. Baran, Bruce Palfey and Bradley S. Moore ()
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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
Bradley S. Moore: Center for Marine Biotechnology and Biomedicine, Scripps Institution of Oceanography, University of California San Diego

Nature, 2013, vol. 503, issue 7477, 552-556

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.

Date: 2013
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DOI: 10.1038/nature12643

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