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Appl Environ Microbiol. 1989 February; 55(2): 330-334
Copyright © 1989, American Society for Microbiology. All Rights Reserved.

Possible Involvement of Toluene-2,3-Dioxygenase in Defluorination of 3-Fluoro-Substituted Benzenes by Toluene-Degrading Pseudomonas sp. Strain T-12

V. Renganathan{dagger}

Smith Kline & French Laboratories, 709 Swedeland Road, King of Prussia, Pennsylvania 19406

ABSTRACT

Pseudomonas sp. strain T-12 cells in which the toluene-degradative pathway enzymes have been induced can transform many 3-fluoro-substituted benzenes to the corresponding 2,3-catechols with simultaneous elimination of the fluorine substituent as inorganic fluoride. Substrates for this transformation included 3-fluorotoluene, 3-fluorotrifluorotoluene, 3-fluorohalobenzenes, 3-fluoroanisole, and 3-fluorobenzonitrile. While 3-fluorotoluene and 3-fluoroanisole produced only defluorinated catechols, other substrates generated catechol products with and without the fluorine substituent. The steric size of the C-1 substituent affected the ratio of defluorinated to fluorinated catechols formed from a substrate. A mechanism for the defluorination reaction involving toluene-2,3-dioxygenase is proposed.

FOOTNOTES

{dagger} Present address: Department of Chemical and Biological Sciences, Oregon Graduate Center, 19600 N. W. Von Neumann Drive, Beaverton, OR 97006-1999.

Appl Environ Microbiol. 1989 February; 55(2): 330-334
Copyright © 1989, American Society for Microbiology. All Rights Reserved.





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