Bacterial metabolism of side chain fluorinated aromatics: cometabolism of 3-trifluoromethyl(TFM)-benzoate by <Emphasis Type="Italic">Pseudomonas putida (arvilla)</Emphasis> mt-2 and <Emphasis Type="Italic">Rhodococcus rubropertinctus</Emphasis> n657

The TOL plasmid-encoded enzymes of the methylbenzoate pathway in Pseudomonas putido mt-2 cometabolized 3-trifluoromethyl (TFM)-benzoate. Two products, 3-TFM -1,2-dihydroxy-2-hydrobcnzoate (3TFM-DHB) and 2-hydroxy-6-oxo-7,7, 7-trifluoro-hepta-2,4-dienoate (7TFHOD) were identified chemically and by spectroscopic properties. TFM-substituted analogues of the metabolites of the methylbenzoate pathway were generally converted at drastically reduced rates. The catechol-2,3-dioxygenase from Pseudomonas pUlido showed moderate turnover rates with 3-TFM-catcchol. The catechol-l,2-dioxygenase of Rhodococcus rubropertinccus N657 was totally inhibited by 3-TFM-catechol and did not cleave this substrate. Hammetttype analysis showed the catechol-l,2-dioxygenase reaction to be strongly dependent on the electronic nature of the substituents. Electronegative substituents strongly inhibited catechol cleavage. The catcchol-2,3-dioxygenase reaction, however, was only moderately sensitive to electronegative