Bacterial metabolism of side-chain-fluorinated aromatics: unproductive meta-cleavage of 3-trifluoromethylcatechol.
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.
Engesser
K H
KH
Institut für Mikrobiologie, Universität Stuttgart, Federal Republic of Germany.
Rubio
M A
MA
Knackmuss
H J
HJ
D001419:Bacteria / Q000201:enzymology / Q000302:isolation & purification / Q000378:metabolism*; D002396:Catechols / Q000378:metabolism*; D005464:Fluorobenzenes / Q000378:metabolism; D006845:Hydrocarbons, Fluorinated / Q000378:metabolism*; D006867:Hydrolases / Q000378:metabolism; D013379:Substrate Specificity
D002396:Catechols; D005464:Fluorobenzenes; D006845:Hydrocarbons, Fluorinated; C065229:3-trifluoromethylcatechol; C044697:benzotrifluoride; D006867:Hydrolases; C021416:2-hydroxy-6-oxo-2,4-heptadienoate hydrolase