A meta cleavage pathway for 4-chlorobenzoate, an intermediate in the metabolism of 4-chlorobiphenyl by Pseudomonas cepacia P166

Bacterial degradation of biphenyl and polychlorinated biphenyls proceeds by a well-studied pathway which produces benzoate and 2-hydroxypent-2,4-dienoate (or, in the case of polychlorinated biphenyls, the chlorinated derivatives of these compounds). Pseudomonas cepacia P166 utilizes 4-chlorobiphenyl...

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Bibliographic Details
Published in:Applied and Environmental Microbiology 1995-02, Vol.61 (2), p.443-447
Main Authors: Arensdorf, J.J. (Foth and Van Dyke, Green Bay, WI.), Focht, D.D
Format: Article
Language:English
Subjects:
ACIDE BENZOIQUE
ACIDO BENZOICO
Bacteriology
BIFENIL
Biochemistry
BIODEGRADACION
BIODEGRADATION
Biodegradation, Environmental
Biphenyl Compounds - chemistry
Biphenyl Compounds - metabolism
BIPHENYLE
Burkholderia cepacia - metabolism
Chlorobenzoates - chemistry
Chlorobenzoates - metabolism
COMPOSE ORGANOCHLORE
COMPUESTO ORGANICO DEL CLORO
ESTER
ESTERES
Gas Chromatography-Mass Spectrometry
METABOLISME
METABOLISMO
METABOLITE
METABOLITOS
Models, Chemical
PSEUDOMONAS CEPACIA
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Summary:Bacterial degradation of biphenyl and polychlorinated biphenyls proceeds by a well-studied pathway which produces benzoate and 2-hydroxypent-2,4-dienoate (or, in the case of polychlorinated biphenyls, the chlorinated derivatives of these compounds). Pseudomonas cepacia P166 utilizes 4-chlorobiphenyl for growth and produces 4-chlorobenzoate as a central intermediate. In this study we found that strain P166 further transforms 4-chlorobenzoate to 4-chlorocatechol, which is mineralized by a meta cleavage pathway. Key metabolites which we identified include the meta cleavage product (5-chloro-2-hydroxymuconic semialdehyde), 5-chloro-2-hydroxymuconate, 5-chloro-2-oxopent-4-enoate, 5-chloro-4-hydroxy-2-oxopentanoate, and chloroacetate. Chloroacetate accumulated transiently, and slow but stoichiometric dehalogenation was observed
ISSN:0099-2240
1098-5336
DOI:10.1128/AEM.61.2.443-447.1995