Metabolism of Halophenols by 2,4,5-trichlorophenoxyacetic acid-degrading Pseudomonas cepacia

Karns, Jeffrey S.; Kilbane, John J.; Duttagupta, Swadesh; Chakrabarty, Ananda M.

doi:10.1128/aem.46.5.1176-1181.1983

Cited by 99 publications

(36 citation statements)

References 17 publications

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“…Many of the pentachlorophenol-degrading strains are able to also degrade several tetraand trichlorophenols, but have low activity for mono-and dichlorophenols [43,[46][47][48][49][50][51]. The degradation of pentachlorophenol and other polychlorophenols was shown to be inducible in several of the strains [43,[47][48][49]52,53]. Those isolates for which the initial reactions are known degrade polychlorinated phenols by mechanisms in which the chlorine substituents are removed before cleavage of the aromatic ring.…”

Section: Aerobic Bacterial Degradation Of Halophenolsmentioning

confidence: 99%

“…A 2,4,5-trichlorophenoxyacetic acid-degrading Pseudomonas cepacia, strain ACll00, also degraded chlorophenols through para-hydroquinone intermediates. 2,4,5-Trichlorophenoxyacetate was initially metabolized to 2,4,5-trichlorophenol [47], and further degraded through 2,5-dichloro-para-hydroquinone and 5-chloro-l,2,4-trihydroxybenzene [61]. This bacterium thus utilizes a pathway similar to that of the pentachlorophenol-mineralizing Rhodococcus strains, in which chlorophenols are degraded through chlorinated 1,2,4-trihydroxybenzenes.…”

Section: Aerobic Bacterial Degradation Of Halophenolsmentioning

confidence: 99%

“…From this mixed culture, Kilbane et al [170] isolated a pure culture of Pseudomonas cepacia designated strain ACll00 that utilized 2,4,5-T as a sole source of carbon and energy. The bacterium degraded 2,4,5-T via 2,4,5-trichlorophenol with essentially 100% release of chloride [47,170,171]. Resting cells of 2,4,5-T-grown P. cepacia strain AC1100 were also able to degrade several other polychlorinated phenols, including pentachlorophenol [47].…”

Section: Aerobic Degradation Of Chlorophenoxyalkanoic Acidsmentioning

confidence: 99%

“…The bacterium degraded 2,4,5-T via 2,4,5-trichlorophenol with essentially 100% release of chloride [47,170,171]. Resting cells of 2,4,5-T-grown P. cepacia strain AC1100 were also able to degrade several other polychlorinated phenols, including pentachlorophenol [47]. Conversion of 2,4,5-T was constitutively expressed, while degradation of chlorophenols was induced by 2,4,5-trichlorophenol [171].…”

Section: Aerobic Degradation Of Chlorophenoxyalkanoic Acidsmentioning

confidence: 99%

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Microbial breakdown of halogenated aromatic pesticides and related compounds

Häggblom

1992

FEMS Microbiology Letters

363

132

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Considerable progress has been made in the last few years in understanding the mechanisms of microbial degradation of halogenated aromatic compounds. Much is already known about the degradation mechanisms under aerobic conditions, and metabolism under anaerobiosis has lately received increasing attention. The removal of the halogen substituent is a key step in degradation of halogenated aromatics. This may occur as an initial step via reductive, hydrolytic or oxygenolytic mechanisms, or after cleavage of the aromatic ring at a later stage of metabolism. In addition to degradation, several biotransformation reactions, such as methylation and polymerization, may take place and produce more toxic or recalcitrant metabolites. Studies with pure bacterial and fungal cultures have given detailed information on the biodegradation pathways of several halogenated aromatic compounds. Several of the key enzymes have been purified or studied in cell extracts, and there is an increasing understanding of the organization and regulation of the genes involved in haloaromatic degradation. This review will focus on the biodegradation and biotransformation pathways that have been established for halogenated phenols, phenoxyalkanoic acids, benzoic acids, benzenes, anilines and structurally related halogenated aromatic pesticides. There is a growing interest in developing microbiological methods for clean‐up of soil and water contaminated with halogenated aromatic compounds.

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Section: Aerobic Bacterial Degradation Of Halophenolsmentioning

confidence: 99%

Section: Aerobic Bacterial Degradation Of Halophenolsmentioning

confidence: 99%

Section: Aerobic Degradation Of Chlorophenoxyalkanoic Acidsmentioning

confidence: 99%

Section: Aerobic Degradation Of Chlorophenoxyalkanoic Acidsmentioning

confidence: 99%

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Microbial breakdown of halogenated aromatic pesticides and related compounds

Häggblom

1992

FEMS Microbiology Letters

363

132

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“…Aerobic degradation of polychlorinated phenols has been observed in soil, water, bioreactors, and mixed bacterial cultures , BROWN et al 1986, ETZEL and KIRSCH 1974, KIRSCH and ETZEL 1973, KLECKA and MAIER 1985, LIU et al 1982, MOOS et al 1983, PIGNATELLO et al 1983, VALO et al 1985, WATANABE 1978, and several aerobic bacteria that degrade pentachlorophenol have been isolated , CHU and KIRSCH 1972. 1973, EDCEHILL and FINN 1982, HAGGBLOM et al 1988d, KARNS et al 1983a, REINER et al 1978, SABER and CRAWFORD 1985, STANLAKE and FINN 1982, SUZUKI 1977, WATANABE 1973. The gram-positive isolates that have been identified belong to the genera Rhodococcus , HAGGBLOM et al 1988d or Mycobacterium (HAGGBLOM et a].…”

Section: Aerobic Degradation Of Polychloroplienolsmentioning

confidence: 99%

Mechanisms of bacterial degradation and transformation of chlorinated monoaromatic compounds

Häggblom

1990

J. Basic Microbiol.

115

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Chloroaromatics are xenobiotic compounds of environmental concern. They can be removed from the environment by (bio)degradation or by (bio)transformation. Recognition of the mechanisms and requirements of their biodegradation is of cardinal importance for understanding the fate of these chemicals in the environment, and for developing methods for biological treatment of wastes containing compounds of this type. Cleavage of the carbon-halogen bond is the critical step in degradation of chloroaromatics. As exemplified with chlorophenols, chlorobenzoates and chlorobenzenes in this review, two distinct strategies are employed by bacteria for degradation of chlorinated aromatic compounds: the particular chlorine substituents are removed either directly from the aromatic ring (as an initial step in degradation) or after oxygenative ring cleavage (from chlorinated aliphatic intermediates). Direct elimination of chlorine substituents from the aromatic ring occurs by displacement with either hydroxyl groups (hydrolytically or oxygenolytically) or hydrogen atoms (reductive dechlorination). Dechlorinations of the latter type require reducing power and are significant in anaerobic environments, but have also been observed with strictly aerobic bacteria. Various biotransformation reactions, with only minor alteration of the parent compound, are an alternative to biogradation. Two environmentally significant transformation reactions discussed here are O-methylation and O-demethylation. The capability to O-methylate chlorinated hydroxybenzenes seems to be widespread in bacteria. O-Methylation is an environmentally important transformation reaction, since methylation increases the lipophilicity of the compound and thus the potential for bioaccumulation. Bacterial O-demethylation of chlorinated methoxylated compounds has been observed under both aerobic and anaerobic conditions.

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