Role of electron-donating cosubstrates in the anaerobic biotransformation of chlorophenoxyacetates to chlorophenols by a bacterial consortium enriched on phenoxyacetate.
A bacterial consortium that anaerobically mineralized phenoxyacetate, with transient production of phenol as an intermediate, was obtained from a methanogenic aquifer site near the Norman, OK municipal landfill. This consortium was able to convert the eight halogenated chlorophenoxyacetates tested to the corresponding chlorophenols. The chlorophenols were not subsequently metabolized. The addition of reduced substrates increased the rate of degradation of all chlorophenoxyacetates, with 78% of mono- and di-chlorinated substrates being transformed to chlorophenols in butyrate-amended cultures, compared to less than 37% transformed in unsupplemented cultures. Butyrate increased the transformation of 2,4,5-trichlorophenoxyacetate from 10% to 20%. An experiment evaluating the effects of several compounds on the side-chain cleavage reaction of 3-chlorophenoxyacetate showed that addition of compounds which readily act as hydrogen donors (butyrate, crotonate, ethanol, propionate, and hydrogen) resulted in 2 to 5 times the amount of 3-chlorophenoxyacetate transformed compared to controls with no amendment, formate had a slight stimulatory effect, and acetate and methanol had no effect. Butyrate addition also increased the rate of phenoxyacetate degradation, resulting in transient phenol accumulation not observed in butyrate-unamended controls. These results support the hypothesis that the side-chain cleavage of phenoxyacetate is a reductive process that is stimulated by the oxidation of reduced cosubstrates.
Gibson
S A
SA
Department of Botany and Microbiology, University of Oklahoma, Norman 73019-0245.
Suflita
J M
JM
D015085:2,4,5-Trichlorophenoxyacetic Acid / Q000493:pharmacokinetics*; D000693:Anaerobiosis; D001711:Biotransformation; D002733:Chlorophenols / Q000493:pharmacokinetics*; D004583:Electrons; D006540:Herbicides / Q000493:pharmacokinetics; D010084:Oxidation-Reduction; D010642:Phenoxyacetates / Q000378:metabolism / Q000494:pharmacology*
D002733:Chlorophenols; D006540:Herbicides; D010642:Phenoxyacetates; D015085:2,4,5-Trichlorophenoxyacetic Acid