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

doi:10.1002/anie.201503654

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

Department of Physics

Research output: Contribution to journal › Article › peer-review

53 Scopus citations

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 language	English
Pages (from-to)	8997-9000
Number of pages	4
Journal	Angewandte Chemie - International Edition
Volume	54
Issue number	31
DOIs	https://doi.org/10.1002/anie.201503654
State	Published - 1 Jul 2015

Bibliographical note

Publisher Copyright:
© 2015 The Authors. Published by Wiley-VCH Verlag GmbH & Co. KGaA.

Keywords

EPR spectroscopy
amines
enzymes
oxidation
reaction mechanisms

Access to Document

10.1002/anie.201503654

Cite this

Murray, A. T., Dowley, M. J. H., Pradaux-Caggiano, F., Baldansuren, A., Fielding, A. J., Tuna, F., Hendon, C. H., Walsh, A., Lloyd-Jones, G. C., John, M. P., & 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

@article{4b2ec13b8c29460792dec9417e58fe70,

title = "Catalytic Amine Oxidation under Ambient Aerobic Conditions: Mimicry of Monoamine Oxidase B",

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.",

keywords = "EPR spectroscopy, amines, enzymes, oxidation, reaction mechanisms",

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

note = "Publisher Copyright: {\textcopyright} 2015 The Authors. Published by Wiley-VCH Verlag GmbH & Co. KGaA.",

year = "2015",

month = jul,

day = "1",

doi = "10.1002/anie.201503654",

language = "English",

volume = "54",

pages = "8997--9000",

journal = "Angewandte Chemie - International Edition",

issn = "1433-7851",

publisher = "John Wiley and Sons Ltd",

number = "31",

}

TY - JOUR

T1 - Catalytic Amine Oxidation under Ambient Aerobic Conditions

T2 - Mimicry of Monoamine Oxidase B

AU - Murray, Alexander T.

AU - Dowley, Myles J.H.

AU - Pradaux-Caggiano, Fabienne

AU - Baldansuren, Amgalanbaatar

AU - Fielding, Alistair J.

AU - Tuna, Floriana

AU - Hendon, Christopher H.

AU - Walsh, Aron

AU - Lloyd-Jones, Guy C.

AU - John, Matthew P.

AU - Carbery, David R.

PY - 2015/7/1

Y1 - 2015/7/1

N2 - 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.

AB - 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.

KW - EPR spectroscopy

KW - amines

KW - enzymes

KW - oxidation

KW - reaction mechanisms

UR - http://www.scopus.com/inward/record.url?scp=84937725311&partnerID=8YFLogxK

U2 - 10.1002/anie.201503654

DO - 10.1002/anie.201503654

M3 - Article

C2 - 26087676

AN - SCOPUS:84937725311

SN - 1433-7851

VL - 54

SP - 8997

EP - 9000

JO - Angewandte Chemie - International Edition

JF - Angewandte Chemie - International Edition

IS - 31

ER -

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

Abstract

Bibliographical note

Keywords

Access to Document

Fingerprint

Cite this