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Issue 14, 2011
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Mechanistic investigations on the efficient catalytic decomposition of peroxynitrite by ebselen analogues

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Abstract

In this study, ebselen and its analogues are shown to be catalysts for the decomposition of peroxynitrite (PN). This study suggests that the PN-scavenging ability of selenenyl amides can be enhanced by a suitable substitution at the phenyl ring in ebselen. Detailed mechanistic studies on the reactivity of ebselen and its analogues towards PN reveal that these compounds react directly with PN to generate highly unstable selenoxides that undergo a rapid hydrolysis to produce the corresponding seleninic acids. The selenoxides interact with nitrite more effectively than the corresponding seleninic acids to produce nitrate with the regeneration of the selenenyl amides. Therefore, the amount of nitrate formed in the reactions mainly depends on the stability of the selenoxides. Interestingly, substitution of an oxazoline moiety on the phenyl ring stabilizes the selenoxide, and therefore, enhances the isomerization of PN to nitrate.

Graphical abstract: Mechanistic investigations on the efficient catalytic decomposition of peroxynitrite by ebselen analogues

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Publication details

The article was received on 22 Dec 2010, accepted on 20 Apr 2011 and first published on 21 Apr 2011


Article type: Paper
DOI: 10.1039/C0OB01234C
Citation: Org. Biomol. Chem., 2011,9, 5193-5200
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    Mechanistic investigations on the efficient catalytic decomposition of peroxynitrite by ebselen analogues

    K. P. Bhabak, A. A. Vernekar, S. R. Jakka, G. Roy and G. Mugesh, Org. Biomol. Chem., 2011, 9, 5193
    DOI: 10.1039/C0OB01234C

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