Monoamine Oxidase (MAO-N) Biocatalyzed Synthesis of Indoles from Indolines Prepared via Photocatalytic Cyclization/Arylative Dearomatization

Fei Zhao, Domiziana Masci, Salvatore Ferla, Carmine Varricchio, Andrea Brancale, Serena Colonna, Gary Black, Nicholas Turner, Daniele Castagnolo

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3 Citations (Scopus)
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Abstract

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.
Original languageEnglish
Pages (from-to)6414–6421
Number of pages8
JournalACS Catalysis
Volume10
Issue number11
Early online date11 May 2020
DOIs
Publication statusPublished - 5 Jun 2020

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