Evidence for novel mechanisms of polychlorinated biphenyl metabolism in Alcaligenes eutrophus H850
- 1 May 1987
- journal article
- research article
- Published by American Society for Microbiology in Applied and Environmental Microbiology
- Vol. 53 (5) , 1103-1112
- https://doi.org/10.1128/aem.53.5.1103-1112.1987
Abstract
Previous studies indicated that Alcaligenes eutrophus H850 attacks a different spectrum of polychlorinated biphenyl (PCB) cogeners than do most PCB-degrading bacteria and that novel mechanisms of PCB degradation might be involved. To delineate this, we have investigated the differences in congener selectivity and metabolite prodution between H850 and Corynebacterium sp. strain MB1, an organism that apparently degrades PCBs via a 2,3-dioxygenase. H850 exhibited a superior abiltiy to degrade congeners via attack on 2-, 2,4-, 2,5-, or 2,4,5-chlorophenyl rings in PCBs but an inferior ability to degrade congeners via attack on a 4-chlorophenyl ring. Reactivity preferences were also reflected in the products formed from unsymmetrical PCBs; thus MB1 attacked the 2,3-chlorophenyl ring of 2,3,2''5''-tetrachlorobiphenyl to yield 2,5-dichlorobenzoic acid, while H850 attacked the 2,5-chlorophenyl ring to yield 2,3-dichlorobenzoic acid and a novel metabolite, 2'',3'' -dichloroacetophenone. Furthermore, H850 oxidized 2,4,5,2'',4'',5''-hexachlorobiphenyl, a cogener with no adjacent unsubstituted carbons, to 2'',4''5''-trichloroacetophenone. The atypical congener selectivity pattern and novel metabolites produced suggest that A. eutrophus H850 may degrade certain PCB congeners by a new route beginning with attack by some enzyme other than the usual 2,3-dioxygenase.This publication has 24 references indexed in Scilit:
- The origin of the oxygen incorporated during the dehalogenation/hydroxylation of 4-chlorobenzoate by an Arthrobacter spBiochemical and Biophysical Research Communications, 1984
- Identification of an arene oxide metabolite of 2,2′,5,5′-tetrachlorobiphenyl by gas chromatography-mass spectroscopyChemico-Biological Interactions, 1982
- Abbau der 4-Chlorbenzoesäure durch eineArthrobacter-SpeciesArchiv für Mikrobiologie, 1976
- Synthesis of 3- and 4-chlorobenzene oxides. Unexpected trapping results during metabolism of carbon-14-labeled chlorobenzene by hepatic microsomesJournal of the American Chemical Society, 1975
- The degradation of polychlorinated biphenyls by micro-organismsScience of The Total Environment, 1975
- Metabolism of chlorobenzene with hepatic microsomes and solubilized cytochrome P-450 systemsArchives of Biochemistry and Biophysics, 1975
- Deuterium isotope effects during formation of phenols by hepatic monoxygenases. Evidence for an alternative to the arene oxide pathwayBiochemistry, 1975
- Degradation of polychlorinated biphenyls by two species of AchromobacterCanadian Journal of Microbiology, 1973
- Hydroxylation of phenylalanine by Pseudomonas sp.: measurement of an isotope effect following the NIH shiftJournal of the Chemical Society, Perkin Transactions 1, 1973
- Arene Oxides as Intermediates in the Metabolism of Aromatic Substrates: Alkyl and Oxygen Migrations during Isomerization of Alkylated Arene OxidesProceedings of the National Academy of Sciences, 1971