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Selifonov, Sergey A., Jerome E. Gurst and Lawrence P. Wackett. 1995. Regioselective Dioxygenation of ortho-Trifluoromethylbenzoate by Pseudomonas aeruginosa 142: Evidence for 1,2-Dioxygenation as a Mechanism in ortho-Halobenzoate Dehalogenation. EPA/600/J-96/074. Biochem. Biophys. Res. Commun. 213(3):759-767. (ERL,GB X817).
Pseudomonas aeruginosa strain 142 oxidizes 2-halobenzoates via a multicomponent oxygenase (V.Romanov and R.P. Hausinger, J. Bacteriol., 1994, 176(11). The intermediacy of a highly unstable cis-diol in the reaction has been proposed. Direct evidence for this is currently lacking and the stereochemical course of the reaction cannot be inferred from previous studies. In this study, 2-trifluoromethylbenzoate was stoichiometrically oxidized by P. aeruginosa 142 to a chiral product identified as (-)2-trifluoromethyl-cis-1,2-dihydroxy-3,5-cyclohexadiene-1-carboxylic acid. These data rigorously establish a dioxygenative mechanism for 2-halobenzoate metabolism. |
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