Bacterial metabolism of 4-chloro-2-methylphenoxyacetate. Formation of glyoxylate by side-chain cleavage

Y, Gamar; Gaunt, J. K.

doi:10.1042/bj1220527

Cited by 46 publications

(8 citation statements)

References 15 publications

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“…The first catabolic step, cleavage of the ether bond to produce the respective pbenols ( Fig. 1), is apparently mediated by a single enzyme, probable a monooxygenase as described by Tiedje aDd Alexander (1969) and Gamar and Gaunt (1971). An initial ring hydroxylation or reductive elimination of chloride can be excluded.…”

Section: Dis(:ussionmentioning

confidence: 99%

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Metabolism of 2,4-dichlorophenoxyacetic acid, 4-chloro-2-methylphenoxyacetic acid and 2-methylphenoxyacetic acid by Alcaligenes eutrophus JMP 134

et al. 1988

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Abstract. Of eleven substituted phenoxyacetic acids tested, only three (2,4-dichloro-, 4-chloro-2-methyl-and 2-methylphenoxyacetic acid) served as growth substrates for Alcaligenes eutroplws JMP 134. Whereas only one enzyme seems to be responsible for the initial cleavage of the ether bond, there was evidence for the presence of three different phenol hydroxylascs in this strain. 3,5-Dichlorocatechol and 5-ch loro-3-methylca techol, metabolites of the degradation of 2,4-diehlorophenoxyacetic acid and 4-cWoro-2-methylphenoxyacetic acid, respectively, were exclusively metabolized via the ortho-cleavage pathway. 2-Methylphenoxy. acetic acid-grown cells showed sim ultaneous induction of meta-and ortho-cleavage enzymes. Two catechol 1,2-dioxygcnases responsible for o rlho-cleavage of the intcr~ mediate catechols were partially purified and characterized. One of these enzymes converted 3,5-dichlorocatechol considerably faster than catechol or 3-chlorocatechoL A new enzyme for the cycloisomerisation ofmuconates was found , which exhibited high activity against the ring-cleavage products of 3,5-dichlorocatcchol and 4-chlorocatechol, but low activities against 2-chloromuconate and muconate.

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Section: Dis(:ussionmentioning

confidence: 99%

“…In general, the mctabolism is initiated by cleavage of the ether bond (Loos et al 1967;Tiedje and Alexander 1969;Evans et aL 197 1 b;Gamar and Gaunt 1971) followed by orthohydroxylation of t he phenolic product to produce a catechol (Bollag et al 1968a ;Beadle and Smith 1982). Variations of this pathway have been reported.…”

mentioning

confidence: 99%

Metabolism of 2,4-dichlorophenoxyacetic acid, 4-chloro-2-methylphenoxyacetic acid and 2-methylphenoxyacetic acid by Alcaligenes eutrophus JMP 134

et al. 1988

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“…In vitro binding assays of the purified transcriptional activator TfdR shows similar binding to both tfdT/tfdC and tfdR/tfdDII intergenic regions. The transcriptional regulators from the benzoate degradation pathway, CatR1 and CatR2, affected 3-CB-and 2,4-D-related growth capabilities (Laemmli et al, 2000(Laemmli et al, , 2004Trefault et al, 2009). Enzymes involved in the degradation pathway 2,4-D monooxygenase direct the initial cleavage of the ether bond of 2,4-D to be converted to 2,4-DCP in C. necator JMP 134 and other strains (Dietmar et al, 1988;Gamar & Gaunt, 1971;. There are three different phenol hydroxylases responsible for conversion of 2,4-DCP to 3,5-dichlorocatechol (Liu & Chapman, 1984).…”

Section: Genetic Regulation Of 24-d Degradationmentioning

confidence: 97%

Microbial degradation of 2,4-dichlorophenoxyacetic acid: Insight into the enzymes and catabolic genes involved, their regulation and biotechnological implications

Kumar

Trefault

Olaniran

2014

Critical Reviews in Microbiology

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A considerable progress has been made to understand the mechanisms of biodegradation of 2,4-dichlorophenoxyacetic acid (2,4-D). 2,4-D biodegradation pathway has been elucidated in many microorganisms including Cupriavidus necator JMP134 (previously known as Wautersia eutropha, Ralstonia eutropha and Alcaligenes eutrophus) and Pseudomonas strains. It generally involves the side chain removal of 2,4-D by α-ketoglutarate-dependent 2,4-D dioxygenase (tfdA) to form 2,4-dichlorophenol (2,4-DCP); hydroxylation of 2,4-DCP by 2,4-DCP hydroxylase (tfdB) to form dichlorocatechol; ortho or meta cleavage of dichlorocatechol by chlorocatechol 1,2-dioxygenase (tfdC) to form 2,4-dichloro-cis,cis-muconate; conversion of 2,4-dichloro-cis,cis-muconate to 2-chlorodienelactone by chloromuconate cycloisomerase (tfdD); conversion of 2-chlorodienelactone to 2-chloromaleylacetate by chlorodienelactone hydrolase (tfdE) and, finally, conversion of 2-chloromaleylacetate to 3-oxoadepate via maleylacetate by chloromaleylacetate reductase and maleylacetate reductase (tfdF), respectively, which is funnelled to the tricarboxylic acid cycle. The latest review on microbial breakdown of 2,4-D, other halogenated aromatic pesticides, and related compounds was compiled by Haggblom, however, a considerable progress has been made in this area of research since then. Thus, this review focuses on the recent advancement on 2,4-D biodegradation, the enzymes, and genes involved and their biotechlogical implications.

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“…In the first step, the aryl alkyl ether bond is labilised by action of a monooxygenase. The hemiacetals thus generated are chemically unstable, and rearrange to phenols and glyoxylate or homologous a-keto acids (Loos et al 1967a,b,c;Bollag et al 1967;Tiedje and Alexander 1969;Evans et al 1971a,b;Gaunt and Evans 1961;Gamar and Gaunt 1971). These substituted phenols are subject to a second monohydroxylation reaction yielding catechols (Bollag et al 1968;Gaunt and Evans 1971a,b).…”

Section: (Chlorophenoxy)alkanoatesmentioning

confidence: 99%

Biodegradation

1991

Springer Series in Applied Biology

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Bacterial metabolism of 4-chloro-2-methylphenoxyacetate. Formation of glyoxylate by side-chain cleavage

Cited by 46 publications

References 15 publications

Metabolism of 2,4-dichlorophenoxyacetic acid, 4-chloro-2-methylphenoxyacetic acid and 2-methylphenoxyacetic acid by Alcaligenes eutrophus JMP 134

Metabolism of 2,4-dichlorophenoxyacetic acid, 4-chloro-2-methylphenoxyacetic acid and 2-methylphenoxyacetic acid by Alcaligenes eutrophus JMP 134

Microbial degradation of 2,4-dichlorophenoxyacetic acid: Insight into the enzymes and catabolic genes involved, their regulation and biotechnological implications

Biodegradation

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