TY - JOUR
T1 - Regioselective Dioxygenation of ortho-Trifluoromethylbenzoate by Pseudomonas aeruginosa 142
T2 - Evidence for 1,2-Dioxygenation as a Mechanism in ortho-Halobenzoate Dehalogenation
AU - Selifonov, Sergey A.
AU - Gurst, Jerome E.
AU - Wackett, Lawrence P
PY - 1995
Y1 - 1995
N2 - 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, acid. These data rigorously establish a dioxygenative mechanism for 2-halobenzoate metabolism.
AB - 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, acid. These data rigorously establish a dioxygenative mechanism for 2-halobenzoate metabolism.
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U2 - 10.1006/bbrc.1995.2195
DO - 10.1006/bbrc.1995.2195
M3 - Article
C2 - 7654235
AN - SCOPUS:0029084037
SN - 0006-291X
VL - 213
SP - 759
EP - 767
JO - Biochemical and Biophysical Research Communications
JF - Biochemical and Biophysical Research Communications
IS - 3
ER -