Novel degradative pathway of 4-nitrobenzoate in Comamonas acidovorans NBA-10

Groenewegen, P.E.J.; Breeuwer, P.; Helvoort, J.M.L.M. van; Langenhoff, Alette; Vries, Floris P. De; Bont, J.A.M. de

doi:10.1099/00221287-138-8-1599

Cited by 89 publications

(70 citation statements)

References 20 publications

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“…The initial reduction is to a hydroxylamino group via a nitroso intermediate. This can then undergo a mutase-mediated rearrangement to ortho-aminophenols (as in the cases of nitrobenzene [31], 3-nitrophenol [37,38], and 4-chloronitrobenzene [21]) with the later release of ammonia; alternatively, the hydroxylamino compound can be converted directly to the corresponding catechol by a lyase-mediated reaction with direct elimination of ammonia, such as in the degradation of 4-nitrobenzoate (14,15,43), 4-nitrotoluene (16,35), and 3-nitrophenol (27).…”

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Cloning and Characterization of the pnb Genes, Encoding Enzymes for 4-Nitrobenzoate Catabolism in Pseudomonas putida TW3

Hughes

Williams

2001

J Bacteriol

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Pseudomonas putida strain TW3 is able to metabolize 4-nitrotoluene via 4-nitrobenzoate (4NBen) and 3, 4-dihydroxybenzoic acid (protocatechuate [PCA]) to central metabolites. We have cloned, sequenced, and characterized a 6-kbp fragment of TW3 DNA which contains five genes, two of which encode the enzymes involved in the catabolism of 4NBen to PCA. In order, they encode a 4NBen reductase (PnbA) which is responsible for catalyzing the direct reduction of 4NBen to 4-hydroxylaminobenzoate with the oxidation of 2 mol of NADH per mol of 4NBen, a reductase-like enzyme (Orf1) which appears to have no function in the pathway, a regulator protein (PnbR) of the LysR family, a 4-hydroxylaminobenzoate lyase (PnbB) which catalyzes the conversion of 4-hydroxylaminobenzoate to PCA and ammonium, and a second lyase-like enzyme (Orf2) which is closely associated with pnbB but appears to have no function in the pathway. The central pnbR gene is transcribed in the opposite direction to the other four genes. These genes complete the characterization of the whole pathway of 4-nitrotoluene catabolism to the ring cleavage substrate PCA in P. putida strain TW3.

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confidence: 99%

Cloning and Characterization of the pnb Genes, Encoding Enzymes for 4-Nitrobenzoate Catabolism in Pseudomonas putida TW3

Hughes

Williams

2001

J Bacteriol

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“…In addition, nitrated polycyclic aromatic hydrocarbons are formed during a variety of combustion processes and are common environmental contaminants (27). Reduction of the nitro group is a common first step in the biotransformation of nitroaromatic compounds, whether leading to mineralization of the compound (13,22) or to the accumulation of dead-end products, many of which are cytotoxic and/or mutagenic (1,7,10,19,20,33).…”

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Purification and characterization of nitrobenzene nitroreductase from Pseudomonas pseudoalcaligenes JS45

Somerville¹,

Nishino²,

Spain³

1995

J Bacteriol

123

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Pseudomonas pseudoalcaligenes JS45 grows on nitrobenzene as a sole source of carbon, nitrogen, and energy. The catabolic pathway involves reduction to hydroxylaminobenzene followed by rearrangement to o-aminophenol and ring fission (S. F. Nishino and J. C. Spain, Appl. Environ. Microbiol. 59:2520, 1993). A nitrobenzene-inducible, oxygen-insensitive nitroreductase was purified from extracts of JS45 by ammonium sulfate precipitation followed by anion-exchange and gel filtration chromatography. A single 33-kDa polypeptide was detected by denaturing gel electrophoresis. The size of the native protein was estimated to be 30 kDa by gel filtration. The enzyme is a flavoprotein with a tightly bound flavin mononucleotide cofactor in a ratio of 2 mol of flavin per mol of protein. The K m for nitrobenzene is 5 M at an initial NADPH concentration of 0.5 mM. The K m for NADPH at an initial nitrobenzene concentration of 0.1 mM is 183 M. Nitrosobenzene was not detected as an intermediate of nitrobenzene reduction, but nitrosobenzene is a substrate for the enzyme, and the specific activity for nitrosobenzene is higher than that for nitrobenzene. These results suggest that nitrosobenzene is formed but is immediately reduced to hydroxylaminobenzene. Hydroxylaminobenzene was the only product detected after incubation of the purified enzyme with nitrobenzene and NADPH. Hydroxylaminobenzene does not serve as a substrate for further reduction by this enzyme. The products and intermediates are consistent with two two-electron reductions of the parent compound. Furthermore, the low K m and the inducible control of enzyme synthesis suggest that nitrobenzene is the physiological substrate for this enzyme.

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“…The nitro group is reduced through 4-nitrosobenzoate and 4-hydroxylaminobenzoate from which it is directly eliminated as ammonia. These reactions from 4-nitrobenzoate were first reported in the 4-nitrobenzoate degrader Comamonas acidovorans NBA10 (10,11), and similar reactions have since been found in Pseudomonas sp. strain YH102 (L. M. Newman and G. J. Zylstra, unpublished data) and Ralstonia pickettii YH105 (35), but none of these utilize 4-nitrotoluene.…”

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Cloning and Expression of ntnD , Encoding a Novel NAD(P) ⁺ -Independent 4-Nitrobenzyl Alcohol Dehydrogenase from Pseudomonas sp. Strain TW3

2000

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Pseudomonas sp. strain TW3 is able to metabolize 4-nitrotoluene to 4-nitrobenzoate and toluene to benzoate aerobically via a route analogous to the upper pathway of the TOL plasmids. We report the cloning and characterization of a benzyl alcohol dehydrogenase gene (ntnD) which encodes the enzyme for the catabolism of 4-nitrobenzyl alcohol and benzyl alcohol to 4-nitrobenzaldehyde and benzaldehyde, respectively. The gene is located downstream of the previously reported ntn gene cluster. NtnD bears no similarity to the analogous TOL plasmid XylB (benzyl alcohol dehydrogenase) protein either in its biochemistry, being NAD(P) ؉ independent and requiring assay via dye-linked electron transfer, or in its deduced amino acid sequence. It does, however, have significant similarity in its amino acid sequence to other NAD(P) ؉ -independent alcohol dehydrogenases and contains signature patterns characteristic of type III flavin adenine dinucleotide-dependent alcohol oxidases. Reverse transcription-PCR demonstrated that ntnD is transcribed during growth on 4-nitrotoluene, although apparently not as part of the same transcript as the other ntn genes. The substrate specificity of the enzyme expressed from the cloned and overexpressed gene was similar to the activity expressed from strain TW3 grown on 4-nitrotoluene, providing evidence that ntnD is the previously unidentified gene in the pathway of 4-nitrotoluene catabolism. Examination of the 14.8-kb region around the ntn genes suggests that one or more recombination events have been involved in the formation of their current organization.

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Novel degradative pathway of 4-nitrobenzoate in Comamonas acidovorans NBA-10

Cited by 89 publications

References 20 publications

Cloning and Characterization of the pnb Genes, Encoding Enzymes for 4-Nitrobenzoate Catabolism in Pseudomonas putida TW3

Cloning and Characterization of the pnb Genes, Encoding Enzymes for 4-Nitrobenzoate Catabolism in Pseudomonas putida TW3

Purification and characterization of nitrobenzene nitroreductase from Pseudomonas pseudoalcaligenes JS45

Cloning and Expression of ntnD , Encoding a Novel NAD(P) ⁺ -Independent 4-Nitrobenzyl Alcohol Dehydrogenase from Pseudomonas sp. Strain TW3

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Novel degradative pathway of 4-nitrobenzoate in Comamonas acidovorans NBA-10

Cited by 89 publications

References 20 publications

Cloning and Characterization of the pnb Genes, Encoding Enzymes for 4-Nitrobenzoate Catabolism in Pseudomonas putida TW3

Cloning and Characterization of the pnb Genes, Encoding Enzymes for 4-Nitrobenzoate Catabolism in Pseudomonas putida TW3

Purification and characterization of nitrobenzene nitroreductase from Pseudomonas pseudoalcaligenes JS45

Cloning and Expression of ntnD , Encoding a Novel NAD(P) + -Independent 4-Nitrobenzyl Alcohol Dehydrogenase from Pseudomonas sp. Strain TW3

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Cloning and Expression of ntnD , Encoding a Novel NAD(P) ⁺ -Independent 4-Nitrobenzyl Alcohol Dehydrogenase from Pseudomonas sp. Strain TW3