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How do perfluorinated alkanoic acids elicit cytochrome P450 to catalyze methane hydroxylation? An MD and QM/MM study

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How do perfluorinated alkanoic acids elicit cytochrome P450 to catalyze methane hydroxylation? An MD and QM/MM study

Content Provider	Royal Society of Chemistry (RSC)
Author	Shaik, Sason Li, Chunsen
Copyright Year	2013
Abstract	Recent experimental studies show that the usage of perfluoro decanoic acid (PFDA), as a dummy substrate, can elicit P450BM3 to perform hydroxylation of small alkanes, such as methane (Angew. Chem., Int. Ed., 2011, 50, 2720) and propane (Angew. Chem., Int. Ed., 2011, 50, 2720 and Angew. Chem., Int. Ed., 2011, 50, 5315). To comprehend the mechanism whereby PFDA operates to potentiate P450BM3 to catalyze the hydroxylation of small alkanes, we used molecular dynamics (MD) and hybrid quantum mechanical/molecular mechanical (QM/MM) calculations. The MD results show that without the PFDA, methane escapes the active site, while the presence of PFDA can potentially induce a productive Cpd I-Methane juxtaposition for rapid oxidation. Nevertheless, when only a single methane molecule is present near the PFDA, it still escapes the pocket within less than a nanosecond. However, when three methane molecules are present in the pocket, they alternate quasi-periodically such that at all times (within 10 ns), a molecule of methane is always present in the proximity of Cpd I in a reactive conformation. Our results further demonstrate that the PFDA does not exert any electrostatic catalysis, whether the PFDA is in the protonated or deprotonated forms. Taken together, we conclude that methane hydroxylation requires, in addition to PFDA, a high partial pressure of methane that will cause a high methane concentration in the active site. Further study of ethane and propane hydroxylations demonstrates that higher alkane concentration is helpful for all the three small alkanes. Thus for the smallest alkane, methane, at least three molecules are necessary, whereas for the larger ethane, two molecules are needed to force one ethane to be closer to Cpd I. Finally, for propane, a second molecule is helpful but not absolutely necessary; for this molecule the PFDA may well be sufficient to keep propane close to Cpd I for efficient oxidation. We therefore propose that high alkane pressure should assist small alkane hydroxylation by P450 in a manner inversely proportional to the size of the alkanes.
Starting Page	2995
Ending Page	3005
Page Count	11
File Format	HTM / HTML PDF
ISSN	20462069
Volume Number	3
Issue Number	9
Journal	RSC Advances
DOI	10.1039/c2ra22294a
Language	English
Publisher	Royal Society of Chemistry
Access Restriction	Open
Subject Keyword	Methane Partial pressure Hydroxylation PFDA Active site Nanosecond Cytochrome P450 Molecular dynamics Conformational isomerism Angew Propane Quantum tunnelling
Content Type	Text
Resource Type	Article
Subject	Chemistry Chemical Engineering

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