Kinetics and mechanism of the ferroxime(II)-catalysed biomimetic oxidation of 2-aminophenol by dioxygen. A functional phenoxazinone synthase model

Dalton Transactions : an International Journal of Inorganic Chemistry
Tatiana M SimándiAgnes Gömöry

Abstract

[Fe(Hdmg)(2)(MeIm)(2)](1), referred to as ferroxime(II), is the precursor of a selective catalyst for the oxidative dehydrogenation of 2-aminophenol (Hap) to 2-amino-3H-phenoxazine-3-one (apx) by dioxygen under ambient conditions. The superoxoferroxime(III) species has been detected by ES-MS, and a 4-substituted 2-aminophenoxyl free radical by the ESR technique. The kinetics of the reaction was followed spectrophotometrically and by monitoring dioxygen uptake at constant pressure. According to the proposed mechanism, solvolysis of 1 is followed by O(2) binding to afford a superoxoferroxime, which abstracts an H-atom from Hap in the rate-determining step via an H-bonded intermediate, generating the free radical. This is supported by the observed primary deuterium kinetic isotope effect of 2.63. The system studied is a functional phenoxazinone synthase model.

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Citations

Feb 27, 2008·Bioprocess and Biosystems Engineering·Mihaela PuiuDumitru Oancea
Jun 29, 2018·Dalton Transactions : an International Journal of Inorganic Chemistry·Avijit DasAshutosh Ghosh
Apr 7, 2007·Biotechnology and Bioengineering·Heather R LuckariftJim C Spain
Mar 25, 2020·Dalton Transactions : an International Journal of Inorganic Chemistry·Oksana V NesterovaDmytro S Nesterov
Dec 24, 2004·Dalton Transactions : an International Journal of Inorganic Chemistry·Tatiana M SimándiLászló I Simándi
Feb 14, 2014·Dalton Transactions : an International Journal of Inorganic Chemistry·Anangamohan PanjaTarun Kanti Mandal
Dec 12, 2018·PLoS Computational Biology·Aleksandr V ZhuravlevElena V Savvateeva-Popova
Nov 12, 2005·The Journal of Biological Chemistry·Hirokazu SuzukiSueharu Horinouchi
Dec 6, 2020·Journal of Inorganic Biochemistry·Winaki P SohtunRamasamy Mayilmurugan

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