Regioselective dioxygenation of ortho-trifluoromethylbenzoate by Pseudomonas aeruginosa 142: evidence for 1,2-dioxygenation as a mechanism in ortho-halobenzoate dehalogenation.
Pseudomonas aeruginosa strain 142 oxidizes 2-halobenzoates via a multicomponent oxygenase (V. Romanov and R.P. Hausinger, J. Bacteriol., 1994, 176(11), 3368-3374). 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.
Selifonov
S A
SA
Department of Biochemistry, University of Minnesota, St. Paul 55108, USA.
Gurst
J E
JE
Wackett
L P
LP
D001711:Biotransformation; D009682:Magnetic Resonance Spectroscopy; D013058:Mass Spectrometry; D010100:Oxygen / Q000378:metabolism*; D011550:Pseudomonas aeruginosa / Q000378:metabolism*; D013237:Stereoisomerism; D014050:Toluene / Q000031:analogs & derivatives* / Q000378:metabolism
D014050:Toluene; C055606:3-trifluoromethylbenzoate; D010100:Oxygen