Zhao, Fei, Masci, Domiziana, Ferla, Salvatore, Varricchio, Carmine, Brancale, Andrea, Colonna, Serena, Black, Gary, Turner, Nicholas J. and Castagnolo, Daniele (2020) Monoamine Oxidase (MAO-N) Biocatalyzed Synthesis of Indoles from Indolines Prepared via Photocatalytic Cyclization/Arylative Dearomatization. ACS Catalysis, 10 (11). pp. 6414-6421. ISSN 2155-5435
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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.
| Item Type: | Article |
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| Additional Information: | Funding information: We gratefully acknowledge the K. C. Wong Foundation for financial support and the Fellowship to F. Z.; D. M. and D. C. acknowledge the University of Roma “La Sapienza” for Mobility Projects Call for Research Doctorates (no. 2682). S. F. is supported by the Sêr Cymru II programme, which is part-funded by Cardiff University and the European Regional Development Fund through the Welsh Government. |
| Uncontrolled Keywords: | indoles, biocatalysis, MAO-N, aromatization, indolines |
| Subjects: | F100 Chemistry |
| Department: | Faculties > Health and Life Sciences > Applied Sciences |
| Depositing User: | Elena Carlaw |
| Date Deposited: | 30 Jul 2020 08:42 |
| Last Modified: | 03 Mar 2023 17:00 |
| URI: | https://nrl.northumbria.ac.uk/id/eprint/43928 |
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