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Catalytic Amine Oxidation under Ambient Aerobic Conditions: Mimicry of Monoamine Oxidase B

Murray, AT, Dowley, MJH, Pradaux-Caggiano, F, Baldansuren, A, Fielding, AJ, Tuna, F, Hendon, CH, Walsh, A, Lloyd-Jones, GC, John, MP and Carbery, DR (2015) Catalytic Amine Oxidation under Ambient Aerobic Conditions: Mimicry of Monoamine Oxidase B. Angewandte Chemie-International Edition, 54 (31). pp. 8997-9000. ISSN 1433-7851

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Abstract

The flavoenzyme monoamine oxidase (MAO) plays a crucial role in regulating animal behavioural patterns by modulating the levels of key monoamine neurotransmitters such as adrenaline and serotonin. Whilst the biochemical importance of MAO is clear, the mechanistic basis which underpins this enzyme is far from agreed upon. Indeed, in the absence of a bio-relevant synthetic model system, the mechanism by which MAO oxidises amines remains an enigma. Herein we report that combination of a synthetic flavin with alloxan generates a catalyst system for amine oxidation at room temperature, with ambient oxygen acting as terminal oxidant. Mechanistic data is presented, including spectroscopic evidence, to support the conclusion that the reaction proceeds through a radical manifold. This simple dual catalyst system provides the first example of a bio-relevant synthetic model for monoamine oxidase B activity.

Item Type: Article
Uncontrolled Keywords: 03 Chemical Sciences
Subjects: Q Science > QD Chemistry
Divisions: Pharmacy & Biomolecular Sciences
Publisher: Wiley
Date Deposited: 28 Feb 2018 11:20
Last Modified: 28 Feb 2018 11:20
DOI or Identification number: 10.1002/anie.201503654
URI: http://researchonline.ljmu.ac.uk/id/eprint/8146

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