title: Toluene dioxygenase mediated oxidation of halogen-substituted benzoate esters.
abstract: A series of ortho-, meta-, and para- halogen-substituted methyl benzoate esters was subjected to enzymatic dihydroxylation via the whole-cell fermentation with E. coli JM109 (pDTG601A). Only ortho-substituted benzoates were metabolized. Methyl 2-fluorobenzoate yielded one diol regioselectively whereas methyl 2-chloro-, methyl 2-bromo- and methyl 2-iodobenzoates each yielded a mixture of regioisomers. Absolute stereochemistry was determined for all new metabolites. Computational analysis of these results and a possible rationale for the regioselectivity of the enzymatic dihydroxylation is advanced.
authors.affiliation: Department of Chemistry, Brock University, 500 Glenridge Ave, St. Catharines, ON, Canada L2S 3A1.
authors.forename: Vladislav
authors.initials: V
authors.lastname: Semak
authors.forename: Thomas A
authors.initials: TA
authors.lastname: Metcalf
authors.forename: Mary Ann A
authors.initials: MA
authors.lastname: Endoma-Arias
authors.forename: Pavel
authors.initials: P
authors.lastname: Mach
authors.forename: Tomas
authors.initials: T
authors.lastname: Hudlicky
mesh_terms: D019817:Benzoic Acid / Q000737:chemistry*; D004926:Escherichia coli / Q000201:enzymology*; D004952:Esters / Q000737:chemistry* / Q000378:metabolism; D006219:Halogens / Q000737:chemistry*; D015394:Molecular Structure; D010084:Oxidation-Reduction; D010105:Oxygenases / Q000378:metabolism*
chemical_list: D004952:Esters; D006219:Halogens; D019817:Benzoic Acid; D010105:Oxygenases; C023172:toluene dioxygenase