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Int. J. Mol. Sci. 2016, 17(8), 1297; doi:10.3390/ijms17081297

How the Proximal Pocket May Influence the Enantiospecificities of Chloroperoxidase-Catalyzed Epoxidations of Olefins

Department of Chemistry and Biochemistry, Florida International University, 11200 SW 8th St., Miami, FL 33199, USA
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Academic Editor: Samuel De Visser
Received: 27 June 2016 / Revised: 28 July 2016 / Accepted: 1 August 2016 / Published: 9 August 2016
(This article belongs to the Special Issue Computational Modelling of Enzymatic Reaction Mechanisms)
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Abstract

Chloroperoxidase-catalyzed enantiospecific epoxidations of olefins are of significant biotechnological interest. Typical enantiomeric excesses are in the range of 66%–97% and translate into free energy differences on the order of 1 kcal/mol. These differences are generally attributed to the effect of the distal pocket. In this paper, we show that the influence of the proximal pocket on the electron transfer mechanism in the rate-limiting event may be just as significant for a quantitatively accurate account of the experimentally-measured enantiospecificities. View Full-Text
Keywords: heme-thiolate enzymes; chloroperoxidase; cytochrome P450; Compound I; proximal pocket; hydrogen bonding; helix dipole; catalytic reactivity; epoxidation; density functional theory heme-thiolate enzymes; chloroperoxidase; cytochrome P450; Compound I; proximal pocket; hydrogen bonding; helix dipole; catalytic reactivity; epoxidation; density functional theory
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MDPI and ACS Style

Morozov, A.N.; Chatfield, D.C. How the Proximal Pocket May Influence the Enantiospecificities of Chloroperoxidase-Catalyzed Epoxidations of Olefins. Int. J. Mol. Sci. 2016, 17, 1297.

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