The cometabolism of 1- and 2-chloronaphthalene by pseudomonads

Morris, Carolyn; Barnsley, E. A.

doi:10.1139/m82-005

Cited by 34 publications

(23 citation statements)

References 12 publications

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“…The spectrum changed reversibly with change in pH, indicating the presence of a group ionizing with a pK a of 5.8. This value was determined according to Morris and Barnsley [6] and was found to be slightly higher than the value of 5.2, reported by the authors for the 4-chlorocatechol meta cleavage product from a pseudomonad.…”

Section: Identification Of the Meta Cleauage Product As 5-chloro-2-hymentioning

confidence: 48%

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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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Section: Identification Of the Meta Cleauage Product As 5-chloro-2-hymentioning

confidence: 48%

“…[9], in Azotobacter vinelandii [10], in Pseudomonas sp. WR 211 [11] and in naphthalene-degrading pseudomonads [6]. Several properties of the 4-chlorocatecbol meta cleavage product have been described in these papers.…”

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 relaxed substrate specificity seems to be a general property of these enzymes since several bacteria which degrade naphthalene are known to convert 2-chloroand 2-methylnaphthalene to the corresponding 4-substituted salicylates (27,40). Therefore, the DHNDOs from these strains must convert at least 7-substituted 1,2-DHNs.…”

Section: Resultsmentioning

confidence: 99%

Purification and characterization of a 1,2-dihydroxynaphthalene dioxygenase from a bacterium that degrades naphthalenesulfonic acids

et al. 1991

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1,2-Dihydroxynaphthalene dioxygenase was purified to homogeneity from a bacterium that degrades naphthalenesulfonic acids (strain BN6). The enzyme requires Fe2" for maximal activity and consists of eight identical subunits with a molecular weight of about 33,000. Analysis of the NH2-terminal amino acid sequence revealed a high degree of homology (22 of 29 amino acids) with the NH2-terminal amino acid sequence of 2,3-dihydroxybiphenyl dioxygenase from strain Pseudomonas paucimobiis Ql. 1,2-Dihydroxynaphthalene dioxygenase from strain BN6 shows a wide substrate specificity and also cleaves 5-, 6-, and 7-hydroxy-1,2-dihydroxynaphthalene, 2,3-and 3,4-dihydroxybiphenyl, catechol, and 3-methyl-and 4-methylcatechol. Similar activities against the hydroxy-1,2-dihydroxynaphthalenes were also found in cell extracts from naphthalenedegrading bacteria.Amino-and hydroxynaphthalenesulfonic acids (ANS and HNS, respectively) serve as building blocks for the largescale synthesis of azo dyes. Since arylsulfonates are very rare among natural compounds (21), naphthalenesulfonic acids are referred to as xenobiotics. Arylsulfonates are major pollutants of the environment, and the contamination of the Rhine River by sulfur-organic compounds is largely due to this class of compounds (25). Nevertheless, bacteria which degrade naphthalenesulfonic acids have repeatedly been isolated (4, 5, 29-31, 41, 43). Brilon et al. (4, 5) selected pseudomonads which degraded naphthalene-2-sulfonic acid (2NS) and naphthalene-1-sulfonic acid (1NS). The initial reaction in the degradation of iNS and 2NS is catalyzed by a 1,2-dioxygenase which weakens the carbon-sulfur bond.

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“…This highly reactive acyl chloride, if released from the enzyme, should be hydrolyzed to 2-hydroxyhexa-2,4-dienoic acid, which shows an absorption maximum at 290 nm at pH 7.5 (38). In contrast, the product of the metacleavage of 4-chlorocatechol has been identified as 5-chloro-2-hydroxy-6-oxohexadienoic acid (30,45) and shows the typical behavior of classical meta-cleavage products. The ring fission product of 3-chlorocatechol after a distal extradiol cleavage would be the isomeric compound 3-chloro-2-hydroxy-6-oxohexadienoic acid exhibiting the same chromophor.…”

Section: Discussionmentioning

confidence: 99%

Characterization of a 2,3-dihydroxybiphenyl dioxygenase from the naphthalenesulfonate-degrading bacterium strain BN6

et al. 1995

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An extradiol dioxygenase was cloned from the naphthalenesulfonate-degrading bacterial strain BN6 by screening a gene bank for colonies with 2,3-dihydroxybiphenyl dioxygenase activity. DNA sequence analysis of a 1,358-bp fragment revealed an open reading frame of only 486 bp. This is the smallest gene encoding an extradiol dioxygenase found until now. Expression of the gene in a T7 expression vector enabled purification of the enzyme. Gel filtration and sodium dodecyl sulfate-polyacrylamide gel electrophoresis analysis showed that the protein was a dimer with a subunit size of 21.7 kDa. The enzyme oxidized 2,3-dihydroxybiphenyl, 3-isopropylcatechol, 3-and 4-chlorocatechol, and 3-and 4-methylcatechol. Since the ability to convert 3-chlorocatechol is an unusual characteristic for an extradiol-cleaving dioxygenase, this reaction was analyzed in more detail. The deduced amino-terminal amino acid sequence differed from the corresponding sequence of the 1,2-dihydroxynaphthalene dioxygenase, which had been determined earlier from the enzyme purified from this strain. This indicates that strain BN6 carries at least two different extradiol dioxygenases.A bacterial strain (strain BN6) which is able to degrade amino-and hydroxynaphthalenesulfonates is currently being studied in this laboratory. This strain oxidizes substituted naphthalenesulfonates to the corresponding substituted 1,2-dihydroxynaphthalenes by a reaction catalyzed by a desulfonating dioxygenase. Subsequent metabolism of the substituted 1,2-dihydroxynaphthalenes (1,2-DHNs) to substituted salicylates follows the common naphthalene degradative pathway. Strain BN6 does not mineralize naphthalenesulfonates, since the salicylates are not further oxidized (24,25,33,34). Cloning the genes for the metabolism of these naphthalenesulfonates would facilitate mobilization into salicylate-degrading bacterial strains, thereby accomplishing the complete degradation of naphthalenesulfonates in a single strain. Previously, the 1,2-DHN dioxygenase (DHNDO), which is part of this metabolic pathway, was purified to homogeneity and biochemically characterized. The enzyme oxidized 1,2-DHN, 2,3-dihydroxybiphenyl (2,3-DHBP), and some other aromatic diols (25). In the present study, we attempted to clone the corresponding gene from strain BN6. Although we obtained clones derived from strain BN6 which were able to oxidize 2,3-DHBP, the encoded gene was unexpectedly not involved in the degradation of naphthalenesulfonates. The extradiol dioxygenase (DO) encoded by this clone was examined in the present study. MATERIALS AND METHODSBacterial strains and culture conditions. The isolation and characterization of strain BN6 have been described previously (33). The strain has been deposited at the Deutsche Sammlung von Mikroorganismen, Brunswick, Germany, as DSM 6383. For the isolation of genomic DNA, the strain was grown in nutrient broth. Escherichia coli DH5␣ was the host for construction of the genomic library. E. coli JM 109 was used for subcloning and isolation of DNA for sequencing. Fo...

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The cometabolism of 1- and 2-chloronaphthalene by pseudomonads

Cited by 34 publications

References 12 publications

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

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

Purification and characterization of a 1,2-dihydroxynaphthalene dioxygenase from a bacterium that degrades naphthalenesulfonic acids

Characterization of a 2,3-dihydroxybiphenyl dioxygenase from the naphthalenesulfonate-degrading bacterium strain BN6

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