Regioselective Dioxygenation of ortho-Trifluoromethylbenzoate by Pseudomonas aeruginosa 142: Evidence for 1,2-Dioxygenation as a Mechanism in ortho-Halobenzoate Dehalogenation

Sergey A. Selifonov, Jerome E. Gurst, Lawrence P Wackett

Research output: Contribution to journalArticle

12 Scopus citations

Abstract

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.

Original languageEnglish (US)
Pages (from-to)759-767
Number of pages9
JournalBiochemical and Biophysical Research Communications
Volume213
Issue number3
DOIs
StatePublished - Jan 1 1995

Fingerprint Dive into the research topics of 'Regioselective Dioxygenation of ortho-Trifluoromethylbenzoate by Pseudomonas aeruginosa 142: Evidence for 1,2-Dioxygenation as a Mechanism in ortho-Halobenzoate Dehalogenation'. Together they form a unique fingerprint.

  • Cite this