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Molecules 2015, 20(6), 10244-10252; doi:10.3390/molecules200610244

Effect of Methoxy Substituents on the Activation Barriers of the Glutathione Peroxidase-Like Mechanism of an Aromatic Cyclic Seleninate

Department of Chemistry and Biochemistry, Old Dominion University, Hampton Boulevard, Norfolk, VA 23529, USA
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Author to whom correspondence should be addressed.
Academic Editor: Thomas G. Back
Received: 12 May 2015 / Revised: 26 May 2015 / Accepted: 1 June 2015 / Published: 3 June 2015
(This article belongs to the Special Issue Selenium Catalysts and Antioxidants)
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Abstract

Density functional theory (DFT) models including explicit water molecules have been used to model the redox scavenging mechanism of aromatic cyclic seleninates. Experimental studies have shown that methoxy substitutions affect the rate of scavenging of reactive oxygen species differently depending upon the position. Activities are enhanced in the para position, unaffected in the meta, and decreased in the ortho. DFT calculations show that the activation barrier for the oxidation of the selenenyl sulfide, a proposed key intermediate, is higher for the ortho methoxy derivative than for other positions, consistent with the low experimental conversion rate. View Full-Text
Keywords: organoselenium compounds; antioxidants; glutathione peroxidase; density functional theory organoselenium compounds; antioxidants; glutathione peroxidase; density functional theory
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This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. (CC BY 4.0).

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MDPI and ACS Style

Bayse, C.A.; Shoaf, A.L. Effect of Methoxy Substituents on the Activation Barriers of the Glutathione Peroxidase-Like Mechanism of an Aromatic Cyclic Seleninate. Molecules 2015, 20, 10244-10252.

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