NDLI: A Systematic Account on Aromatic Hydroxylation by a Cytochrome P 450 Model Compound

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A Systematic Account on Aromatic Hydroxylation by a Cytochrome P 450 Model Compound

Content Provider	Semantic Scholar
Author	Reinhard, Cantú Sainna, Mala A. Upadhayay, Pranav Balan, G. Alex Devesh Kumar Fornarini, Simonetta Crestoni, Maria Elisa Visser, Sam P. De
Copyright Year	2016
Abstract	Cytochrome P450 enzymes are heme containing monooxygenases that mainly react through oxygen atom transfer. Specific features of substrate and oxidant that determine the reaction rate constant for oxygen atom transfer are still poorly understood and, therefore, we did a systematic gas-phase study on reactions by iron(IV)-oxo porphyrin cation radical structures with arenes. We present here the first results obtained by using Fourier transform-ion cyclotron resonance mass spectrometry and provide rate constants and product distributions for the assayed reactions. Product distributions and kinetic isotope effect studies implicate a rate determining aromatic hydroxylation reaction that correlates with the ionization energy of the substrate and no evidence of aliphatic hydroxylation products is observed. To further understand the details of the reaction mechanism, a computational study on a model complex was performed. These studies confirm the experimental hypothesis of dominant aromatic over aliphatic hydroxylation and show that the lack of an axial ligand affects the aliphatic pathways. Moreover, a two parabola valence bond model is used to rationalize the rate constant and identify key properties of the oxidant and substrate that drive the reaction. In particular, the work shows that aromatic hydroxylation rates correlate with the ionization energy of the substrate as well as with the electron affinity of the oxidant.
File Format	PDF HTM / HTML
Alternate Webpage(s)	https://www.research.manchester.ac.uk/portal/files/50808199/AromaticTrends_Rev5.pdf
Language	English
Access Restriction	Open
Content Type	Text
Resource Type	Article

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