Bacterial metabolism of side-chain-fluorinated aromatics: unproductive meta-cleavage of 3-trifluoromethylcatechol |
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Authors: | Karl-Heinrich Engesser Miguel Angel Rubio Hans-Joachim Knackmuss |
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Institution: | (1) Institut für Mikrobiologie der Universität Stuttgart, Azenbergstrasse 18, D-7000 Stuttgart-1, Federal Republic of Germany;(2) Technische Universität Hamburg-Harburg, Abteilung für Gewässerreinigungstechnik, D-2100 Hamburg 90, Federal Republic of Germany |
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Abstract: | Summary 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.Offprint requests to: K.-H. Engesser |
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