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

The flavoenzyme monoamine oxidase (MAO) regulates mammalian behavioral patterns by modulating neurotransmitters such as adrenaline and serotonin. The mechanistic basis which underpins this enzyme is far from agreed upon. Reported herein is that the combination of a synthetic flavin and alloxan gener...

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Bibliographic Details
Published in:Angewandte Chemie 2015-07, Vol.127 (31), p.9125-9128
Main Authors: Murray, Alexander T., Dowley, Myles J. H., Pradaux-Caggiano, Fabienne, Baldansuren, Amgalanbaatar, Fielding, Alistair J., Tuna, Floriana, Hendon, Christopher H., Walsh, Aron, Lloyd-Jones, Guy C., John, Matthew P., Carbery, David R.
Format: Article
Language:English
Subjects:
Amine
Enzyme
EPR-Spektroskopie
Oxidation
Reaktionsmechanismen
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Summary:The flavoenzyme monoamine oxidase (MAO) regulates mammalian behavioral patterns by modulating neurotransmitters such as adrenaline and serotonin. The mechanistic basis which underpins this enzyme is far from agreed upon. Reported herein is that the combination of a synthetic flavin and alloxan generates a catalyst system which facilitates biomimetic amine oxidation. Mechanistic and electron paramagnetic (EPR) spectroscopic data supports the conclusion that the reaction proceeds through a radical manifold. This data provides the first example of a biorelevant synthetic model for monoamine oxidase B activity. MAO‐Nachahmer: Ein Modellflavin wird als Mimetikum der Monoaminoxidase B (MAO‐B) unter aeroben und Umgebungsbedingungen eingeführt. Kinetik‐ und EPR‐Studien geben Einblick in den Mechanismus: Ein geschwindigkeitsbestimmender Wasserstoffatomtransfer vom Amin zum Flavinakzeptor wird sowohl für das Modellsystem als auch für MAO‐B vorgeschlagen.
ISSN:0044-8249
1521-3757
DOI:10.1002/ange.201503654