Origin of Site Selectivity in Toluene Hydroxylation by Cytochrome P450 Enzymes
Xuan Wu, Chen Yu, Xin Wang, Wanqing Wei, Yong Liang
Abstract
Computational studies are utilized to reveal factors that determine the site selectivity in toluene hydroxylation by cytochrome P450 enzymes (CYPs). The DFT-computed inherent barriers suggest that the priority of product formation is in the order of benzyl alcohol > ortho- ≈ para- > meta-cresol. However, the specific size and shape of the cavities at the active sites of different CYPs dramatically affect the binding orientation of toluene, and thus, the site selectivity can be reordered.
Topics & Concepts
ChemistryTolueneSelectivityHydroxylationCytochrome P450EnzymeStereochemistryCytochromeOrganic chemistryCatalysisPharmacogenetics and Drug MetabolismAnalytical Chemistry and ChromatographyMicrobial Metabolic Engineering and Bioproduction