Biocatalytic and chemo-enzymatic synthesis of quinolines and 2‑quinolones by monoamine oxidase (MAO-N) and horseradish peroxidase (HRP) biocatalysts

Xiang, Haoyue, Ferla, Salvatore, Varricchio, Carmine ORCID: https://orcid.org/0000-0002-1673-4768, Brancale, Andrea ORCID: https://orcid.org/0000-0002-9728-3419, Brown, Nicola L., Black, Gary W., Turner, Nicholas J. and Castagnolo, Daniele 2023. Biocatalytic and chemo-enzymatic synthesis of quinolines and 2‑quinolones by monoamine oxidase (MAO-N) and horseradish peroxidase (HRP) biocatalysts. ACS Catalysis 13 (5) , pp. 3370-3378. 10.1021/acscatal.2c05902

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Abstract

The oxidative aromatization of aliphatic N-heterocycles is a fundamental organic transformation for the preparation of a diverse array of heteroaromatic compounds. Despite many attempts to improve the efficiency and practicality of this transformation, most synthetic methodologies still require toxic and expensive reagents as well as harsh conditions. Herein, we describe two enzymatic strategies for the oxidation of 1,2,3,4-tetrahydroquinolines (THQs) and N-cyclopropyl-N-alkylanilines into quinolines and 2-quinolones, respectively. Whole cells and purified monoamine oxidase (MAO-N) enzymes were used to effectively catalyze the biotransformation of THQs into the corresponding aromatic quinoline derivatives, while N-cyclopropyl-N-alkylanilines were converted into 2-quinolone compounds through a horseradish peroxidase (HRP)-catalyzed annulation/aromatization reaction followed by Fe-mediated oxidation.

Item Type:	Article
Date Type:	Publication
Status:	Published
Schools:	Pharmacy
Additional Information:	License information from Publisher: LICENSE 1: URL: https://creativecommons.org/licenses/by/4.0/, Start Date: 2023-02-22
Publisher:	American Chemical Society
ISSN:	2155-5435
Date of First Compliant Deposit:	7 March 2023
Date of Acceptance:	7 February 2023
Last Modified:	06 Jan 2024 05:11
URI:	https://orca.cardiff.ac.uk/id/eprint/157551

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