Bacterial metabolism of side-chain-fluorinated aromatics: unproductive meta-cleavage of 3-trifluoromethylcatechol.

Bacterial metabolism of side-chain-fluorinated aromatics: unproductive meta-cleavage of 3-trifluoromethylcatechol.

Applied microbiology and biotechnology (1990-02-01)

K H Engesser, M A Rubio, H J Knackmuss

ABSTRACT

Sixteen bacterial strains capable of degrading alkylbenzenes and alkylphenols were directly isolated from soil and water. The degradation pathways are discussed. Alkylcatechols are almost exclusively cleaved via meta-ring fission. Meta-cleavage of 3-trifluoromethyl-(TFM)-catechol was observed with all strains at different rates although the reaction rates compared to catechol as a substrate varied considerably. All 2-hydroxy-6-oxohepta-2,4-dienoic acid hydrolases investigated showed strong binding of 7,7,7-trifluoro-2-hydroxy-6-oxohepta-2,4-dienoic acid, the ring fission product of 3-TFM-catechol. Turnover rates, however, were negligible indicating this compound to be a general dead-end metabolite during metabolism of TFM-substituted compounds via meta-cleavage pathways.

MATERIALS

Product Number

Brand

Product Description

547948

Sigma-Aldrich

α,α,α-Trifluorotoluene, anhydrous, ≥99%

T63703

Sigma-Aldrich

α,α,α-Trifluorotoluene, ≥99%

733806

Sigma-Aldrich

α,α,α-Trifluorotoluene solution, NMR reference standard, 0.05% in benzene-d₆ (99.6 atom % D), NMR tube size 10 mm × 8 in.

551406

Sigma-Aldrich

α,α,α-Trifluorotoluene solution, NMR reference standard, 0.05% in benzene-d₆ (99.6 atom % D)

612685

Sigma-Aldrich

α,α,α-Trifluorotoluene solution, NMR reference standard, 0.05% in benzene-d₆ (99.6 atom % D), NMR tube size 3 mm × 8 in.