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Monoamine Oxidase (MAO-N) Biocatalyzed Synthesis of Indoles from Indolines Prepared via Photocatalytic Cyclization/Arylative Dearomatization
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    Monoamine Oxidase (MAO-N) Biocatalyzed Synthesis of Indoles from Indolines Prepared via Photocatalytic Cyclization/Arylative Dearomatization
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    • Fei Zhao
      Fei Zhao
      School of Cancer and Pharmaceutical Sciences, King’s College London, London SE1 9NH, United Kingdom
      More by Fei Zhao
    • Domiziana Masci
      Domiziana Masci
      School of Cancer and Pharmaceutical Sciences, King’s College London, London SE1 9NH, United Kingdom
    • Salvatore Ferla
      Salvatore Ferla
      School of Pharmacy and Pharmaceutical Sciences, Cardiff University, King Edward VII Avenue, Cardiff CF10 3NB, United Kingdom
    • Carmine Varricchio
      Carmine Varricchio
      School of Pharmacy and Pharmaceutical Sciences, Cardiff University, King Edward VII Avenue, Cardiff CF10 3NB, United Kingdom
    • Andrea Brancale
      Andrea Brancale
      School of Pharmacy and Pharmaceutical Sciences, Cardiff University, King Edward VII Avenue, Cardiff CF10 3NB, United Kingdom
    • Serena Colonna
      Serena Colonna
      School of Cancer and Pharmaceutical Sciences, King’s College London, London SE1 9NH, United Kingdom
    • Gary W. Black
      Gary W. Black
      Department of Applied Sciences, Northumbria University, Ellison Place, Newcastle upon Tyne NE1 8ST, United Kingdom
    • Nicholas J. Turner
      Nicholas J. Turner
      School of Chemistry, Manchester Institute of Biotechnology, University of Manchester, 131 Princess Street, Manchester M1 7DN, United Kingdom
    • Daniele Castagnolo*
      Daniele Castagnolo
      School of Cancer and Pharmaceutical Sciences, King’s College London, London SE1 9NH, United Kingdom
      *E-mail: [email protected]
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    ACS Catalysis

    Cite this: ACS Catal. 2020, 10, 11, 6414–6421
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    https://doi.org/10.1021/acscatal.0c01351
    Published May 11, 2020
    Copyright © 2020 American Chemical Society

    Abstract

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    The biocatalytic aromatization of indolines into indole derivatives exploiting monoamine oxidase (MAO-N) enzymes is presented. Indoline substrates were prepared via photocatalytic cyclization of arylaniline precursors or via arylative dearomatization of unsubstituted indoles and in turn chemoselectively aromatized by the MAO-N D11 whole cell biocatalyst. Computational docking studies of the indoline substrates in the MAO-N D11 catalytic site allowed for the rationalization of the biocatalytic mechanism and experimental results of the biotransformation. This methodology represents an efficient example of biocatalytic synthesis of indole derivatives and offers a facile approach to access these aromatic heterocycles under mild reaction conditions.

    Copyright © 2020 American Chemical Society

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    Supporting Information

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    Cited By

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    This article is cited by 25 publications.

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    ACS Catalysis

    Cite this: ACS Catal. 2020, 10, 11, 6414–6421
    Click to copy citationCitation copied!
    https://doi.org/10.1021/acscatal.0c01351
    Published May 11, 2020
    Copyright © 2020 American Chemical Society

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