Literature DB >> 23417310

Do MAO A and MAO B utilize the same mechanism for the C-H bond cleavage step in catalysis? Evidence suggesting differing mechanisms.

R Orru1, M Aldeco, D E Edmondson.   

Abstract

The detailed molecular mechanism proposed for the MAO-catalyzed oxidation of amines has been controversial with the basic assumption that both MAO A and MAO B follow the same pathway for the C-H bond cleavage step. Using the mechanistic approach of investigation of electronic effects of various benzylamine ring substituents in experiments at pH 9.0, human MAO A exhibits a kinetic behavior characteristic of an H(+) abstraction, while human MAO B exhibits kinetic properties characteristic of a H(-) abstraction. These results lead to the conclusion that the assumption that MAO A and MAO B follow identical mechanisms is incorrect.

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Year:  2013        PMID: 23417310      PMCID: PMC3665653          DOI: 10.1007/s00702-013-0991-3

Source DB:  PubMed          Journal:  J Neural Transm (Vienna)        ISSN: 0300-9564            Impact factor:   3.575


  12 in total

1.  Variations in activity and inhibition with pH: the protonated amine is the substrate for monoamine oxidase, but uncharged inhibitors bind better.

Authors:  T Z E Jones; D Balsa; M Unzeta; R R Ramsay
Journal:  J Neural Transm (Vienna)       Date:  2007-03-31       Impact factor: 3.575

Review 2.  Molecular and mechanistic properties of the membrane-bound mitochondrial monoamine oxidases.

Authors:  Dale E Edmondson; Claudia Binda; Jin Wang; Anup K Upadhyay; Andrea Mattevi
Journal:  Biochemistry       Date:  2009-05-26       Impact factor: 3.162

3.  High-level expression of human liver monoamine oxidase A in Pichia pastoris: comparison with the enzyme expressed in Saccharomyces cerevisiae.

Authors:  Min Li; Frantisĕk Hubálek; Paige Newton-Vinson; Dale E Edmondson
Journal:  Protein Expr Purif       Date:  2002-02       Impact factor: 1.650

4.  Catalytic and inhibitor binding properties of zebrafish monoamine oxidase (zMAO): comparisons with human MAO A and MAO B.

Authors:  Milagros Aldeco; Betül Kacar Arslan; Dale E Edmondson
Journal:  Comp Biochem Physiol B Biochem Mol Biol       Date:  2011-02-23       Impact factor: 2.231

5.  High-level expression of human liver monoamine oxidase B in Pichia pastoris.

Authors:  P Newton-Vinson; F Hubalek; D E Edmondson
Journal:  Protein Expr Purif       Date:  2000-11       Impact factor: 1.650

6.  Structure-activity relationships in the oxidation of para-substituted benzylamine analogues by recombinant human liver monoamine oxidase A.

Authors:  J R Miller; D E Edmondson
Journal:  Biochemistry       Date:  1999-10-12       Impact factor: 3.162

7.  The 'gating' residues Ile199 and Tyr326 in human monoamine oxidase B function in substrate and inhibitor recognition.

Authors:  Erika M Milczek; Claudia Binda; Stefano Rovida; Andrea Mattevi; Dale E Edmondson
Journal:  FEBS J       Date:  2011-11-03       Impact factor: 5.542

8.  Nitrogen kinetic isotope effects for the monoamine oxidase B-catalyzed oxidation of benzylamine and (1,1-(2)H2)benzylamine: nitrogen rehybridization and CH bond cleavage are not concerted.

Authors:  Susanna MacMillar; Dale E Edmondson; Olle Matsson
Journal:  J Am Chem Soc       Date:  2011-07-28       Impact factor: 15.419

Review 9.  Oxidation of amines by flavoproteins.

Authors:  Paul F Fitzpatrick
Journal:  Arch Biochem Biophys       Date:  2009-08-03       Impact factor: 4.013

10.  Structure-activity relationships in the oxidation of benzylamine analogues by bovine liver mitochondrial monoamine oxidase B.

Authors:  M C Walker; D E Edmondson
Journal:  Biochemistry       Date:  1994-06-14       Impact factor: 3.162

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  8 in total

Review 1.  On the practical aspects of characterising monoamine oxidase inhibition in vitro.

Authors:  Andrew Holt
Journal:  J Neural Transm (Vienna)       Date:  2018-10-29       Impact factor: 3.575

Review 2.  Kinetics, mechanism, and inhibition of monoamine oxidase.

Authors:  Rona R Ramsay; Alen Albreht
Journal:  J Neural Transm (Vienna)       Date:  2018-03-07       Impact factor: 3.575

Review 3.  90 years of monoamine oxidase: some progress and some confusion.

Authors:  Keith F Tipton
Journal:  J Neural Transm (Vienna)       Date:  2018-04-10       Impact factor: 3.575

4.  Mechanistic Studies of an Amine Oxidase Derived from d-Amino Acid Oxidase.

Authors:  Elizabeth E Trimmer; Udayanga S Wanninayake; Paul F Fitzpatrick
Journal:  Biochemistry       Date:  2017-04-03       Impact factor: 3.162

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

Authors:  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
Journal:  Angew Chem Int Ed Engl       Date:  2015-06-18       Impact factor: 15.336

Review 6.  The Use of Multiscale Molecular Simulations in Understanding a Relationship between the Structure and Function of Biological Systems of the Brain: The Application to Monoamine Oxidase Enzymes.

Authors:  Robert Vianello; Carmen Domene; Janez Mavri
Journal:  Front Neurosci       Date:  2016-07-15       Impact factor: 4.677

7.  Evidence for a Cyanine Link Between Propargylamine Drugs and Monoamine Oxidase Clarifies the Inactivation Mechanism.

Authors:  Alen Albreht; Irena Vovk; Janez Mavri; Jose Marco-Contelles; Rona R Ramsay
Journal:  Front Chem       Date:  2018-05-28       Impact factor: 5.221

8.  How Monoamine Oxidase A Decomposes Serotonin: An Empirical Valence Bond Simulation of the Reactive Step.

Authors:  Alja Prah; Miha Purg; Jernej Stare; Robert Vianello; Janez Mavri
Journal:  J Phys Chem B       Date:  2020-09-10       Impact factor: 2.991

  8 in total

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