Chlorophenol and chlorobenzoic acid co-metabolism by different genera of soil bacteria

Spokes, J. R.; Walker, Nicola

doi:10.1007/bf00590169

Cited by 51 publications

(23 citation statements)

References 12 publications

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“…Many strains capable of degrading halobenzoates have been described. They are members of the genera Pseudomonas Schreiber et al 1980;Chatterjee et al 1981;Schmidt & Knackmuss 1984;Focht & Shelton 1987;Wyndham & Straus 1988a;Vora et al 1988;Hartmann et al 1989;Schl6mann et al 1990), Alcaligenes (Schmidt & Knackmuss 1984;Schmidt 1988;Wyndham & Straus 1988a;Schl6mann et al 1990), Nocardia (Cain et al 1968;Spokes & Walker 1974) and Azotobacter (Walker & Harris 1970). Strain FLB 300 which is able to degrade all three monofluorobenzoates was assigned to the Agrobacterium-Rhizobium group (Engesser et al 1990).…”

Section: Degradation Of Halogenated Benzoic Acidsmentioning

confidence: 99%

Degradation of halogenated aromatic compounds

1990

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Due to their persistence, haloaromatics are compounds of environmental concern. Aerobically, bacteria degrade these compounds by mono- or dioxygenation of the aromatic ring. The common intermediate of these reactions is (halo)catechol. Halocatechol is cleaved either intradiol (ortho-cleavage) or extradiol (meta-cleavage). In contrast to ortho-cleavage, meta-cleavage of halocatechols yields toxic metabolites. Dehalogenation may occur fortuitously during oxygenation. Specific dehalogenation of aromatic compounds is performed by hydroxylases, in which the halo-substituent is replaced by a hydroxyl group. During reductive dehalogenation, haloaromatic compounds may act as electron-acceptors. Herewith, the halosubstituent is replaced by a hydrogen atom.

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Section: Degradation Of Halogenated Benzoic Acidsmentioning

confidence: 99%

Degradation of halogenated aromatic compounds

1990

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“…Among these compounds are chlorobenzene [1], chlorophenols [2], chlorophenoxyacetates [3], chlorobenzoates [4], chloroanilines [5] and chloronaphthalenes [6]. Further degradation proceeds via ring fission of the chlorocatechol intermediate.…”

Section: Introductionmentioning

confidence: 99%

Metabolism of 4-chlorophenol by Azotobacter sp. GP1: Structure of the meta cleavage product of 4-chlorocatechol

Wieser

1994

FEMS Microbiology Letters

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A mutant strain of Azotobacter sp. GP1 converted 4-chlorophenol to 4-chlorocatechol under cometabolic conditions. Under the same conditions the wild-type strain accumulated a yellow compound, which by chemical and spectroscopic methods was identified as 5-chloro-2-hydroxy-6-oxohexadienoic acid (5-chloro-2-hydroxy-muconic semialdehyde). The structure of this compound indicates a meta-proximal cleavage of 4-chlorocatechol.

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“…Studies by Ide et al ), Neilson et al (1983), and Suzuki (1983b have demonstrated methylation as a mechanism of metabolism with the chlorophenol derivative being converted into its corresponding anisole (i.e., a methyl group being attached through an ester linkage to the former hydroxy group). An alternative pathway is via oxidation which results in the formation of chlorocatechol derivatives (i.e., 1,2-dihydroxybenzenes) from the corresponding chlorophenol (Spokes and Walker 1974;Knackmuss and Hellwig 1978; Suzuki 1983b; Chaudhry and Chapalmadugu 1991). The structural complexity of PCP coupled with the variety of metabolic pathways provides the potential for the formation of a variety of metabolic intermediates.…”

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confidence: 99%

Toxicological assessment of biotransformation products of pentachlorophenol: Tetrahymena population growth impairment

Bryant

Schultz

1994

Arch. Environ. Contam. Toxicol.

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Pentachlorophenol (PCP) is a widespread contaminate of soils and ground water throughout North America. Earlier studies have indicated that microbial biodegradation leads to the formation of intermediate metabolites which are more toxic than the parent compound. Microbial degradation is by three general pathways: dechlorination, methylation, and oxidation. The relative toxicity of PCP and 25 of its identified intermediates of microbial transformation was evaluated in the static Tetrahymena pyriformis population growth assay. Dechlorination of chlorophenols resulted in a decrease in toxicity because of a decrease in both hydrophobicity and reactivity. Moreover, dechlorination of chloroanisoles resulted in a decrease in toxicity due to a decrease in hydrophobicity. Since there was a decrease in reactivity, methylation of chlorophenols resulted in a decrease in toxicity. Oxidation of chlorophenols resulted in enhanced toxicity owing to increased reactivity and concomitant decreased hydrophobicity.

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Chlorophenol and chlorobenzoic acid co-metabolism by different genera of soil bacteria

Cited by 51 publications

References 12 publications

Degradation of halogenated aromatic compounds

Degradation of halogenated aromatic compounds

Metabolism of 4-chlorophenol by Azotobacter sp. GP1: Structure of the meta cleavage product of 4-chlorocatechol

Toxicological assessment of biotransformation products of pentachlorophenol: Tetrahymena population growth impairment

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