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Open AccessFeature PaperArticle

Path Integral Calculation of the Hydrogen/Deuterium Kinetic Isotope Effect in Monoamine Oxidase A-Catalyzed Decomposition of Benzylamine

1
Faculty of Chemistry, Jagiellonian University, 30-387 Kraków, Poland
2
National Institute of Chemistry, SI–1000 Ljubljana, Slovenia
3
Faculty of Pharmacy, University of Ljubljana, SI-1000 Ljubljana, Slovenia
*
Author to whom correspondence should be addressed.
Molecules 2019, 24(23), 4359; https://doi.org/10.3390/molecules24234359
Received: 28 October 2019 / Revised: 21 November 2019 / Accepted: 24 November 2019 / Published: 28 November 2019
(This article belongs to the Special Issue Isotope Effects 2019)
Monoamine oxidase A (MAO A) is a well-known enzyme responsible for the oxidative deamination of several important monoaminergic neurotransmitters. The rate-limiting step of amine decomposition is hydride anion transfer from the substrate α–CH2 group to the N5 atom of the flavin cofactor moiety. In this work, we focus on MAO A-catalyzed benzylamine decomposition in order to elucidate nuclear quantum effects through the calculation of the hydrogen/deuterium (H/D) kinetic isotope effect. The rate-limiting step of the reaction was simulated using a multiscale approach at the empirical valence bond (EVB) level. We applied path integral quantization using the quantum classical path method (QCP) for the substrate benzylamine as well as the MAO cofactor flavin adenine dinucleotide. The calculated H/D kinetic isotope effect of 6.5 ± 1.4 is in reasonable agreement with the available experimental values. View Full-Text
Keywords: monoamine oxidase; kinetic isotope effect; quantum classical path monoamine oxidase; kinetic isotope effect; quantum classical path
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MDPI and ACS Style

Brela, M.Z.; Prah, A.; Boczar, M.; Stare, J.; Mavri, J. Path Integral Calculation of the Hydrogen/Deuterium Kinetic Isotope Effect in Monoamine Oxidase A-Catalyzed Decomposition of Benzylamine. Molecules 2019, 24, 4359.

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