Catalytic amine oxidation under ambient aerobic conditions

mimicry of monoamine oxidase B

Alexander T. Murray, Myles J H Dowley, Fabienne Pradaux-Caggiano, Amgalanbaatar Baldansuren, Alistair J. Fielding, Floriana Tuna, Christopher H. Hendon, Aron Walsh, Guy C. Lloyd-Jones, Matthew P. John, David R. Carbery

Research output: Contribution to journalArticle

25 Citations (Scopus)

Abstract

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.

Original languageEnglish
Pages (from-to)8997-9000
Number of pages4
JournalAngewandte Chemie-International Edition
Volume54
Issue number31
Early online date18 Jun 2015
DOIs
Publication statusPublished - 27 Jul 2015

Fingerprint

Monoamine Oxidase
Amines
Biomimetics
Alloxan
Epinephrine
Neurotransmitter Agents
Serotonin
Electrons
Enzymes
4,6-dinitro-o-cresol

Keywords

  • amines
  • enzymes
  • EPR spectroscopy
  • oxidation
  • reaction mechanisms

Cite this

Murray, A. T., Dowley, M. J. H., Pradaux-Caggiano, F., Baldansuren, A., Fielding, A. J., Tuna, F., ... Carbery, D. R. (2015). Catalytic amine oxidation under ambient aerobic conditions: mimicry of monoamine oxidase B. Angewandte Chemie-International Edition, 54(31), 8997-9000. https://doi.org/10.1002/anie.201503654

Catalytic amine oxidation under ambient aerobic conditions : mimicry of monoamine oxidase B. / 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.

In: Angewandte Chemie-International Edition, Vol. 54, No. 31, 27.07.2015, p. 8997-9000.

Research output: Contribution to journalArticle

Murray, AT, Dowley, MJH, Pradaux-Caggiano, F, Baldansuren, A, Fielding, AJ, Tuna, F, Hendon, CH, Walsh, A, Lloyd-Jones, GC, John, MP & Carbery, DR 2015, 'Catalytic amine oxidation under ambient aerobic conditions: mimicry of monoamine oxidase B', Angewandte Chemie-International Edition, vol. 54, no. 31, pp. 8997-9000. https://doi.org/10.1002/anie.201503654
Murray AT, Dowley MJH, Pradaux-Caggiano F, Baldansuren A, Fielding AJ, Tuna F et al. Catalytic amine oxidation under ambient aerobic conditions: mimicry of monoamine oxidase B. Angewandte Chemie-International Edition. 2015 Jul 27;54(31):8997-9000. https://doi.org/10.1002/anie.201503654
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. / Catalytic amine oxidation under ambient aerobic conditions : mimicry of monoamine oxidase B. In: Angewandte Chemie-International Edition. 2015 ; Vol. 54, No. 31. pp. 8997-9000.
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