Bacterial degradation of the nitrobenzoic acids

Cartwright, N. J.; Cain, Ronald B.

doi:10.1042/bj0710248

Cited by 90 publications

(51 citation statements)

References 37 publications

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“…In the isolate Comamonas acidovorans NBA-10 the initial attack in the degradation of 4-NBA is on the nitro-group as reported for the 4-NBA-degrading bacterium Pseudomonas Juorescens (Durham, 1958;Cartwright & Cain, 1959 b) and for Nocardia erythropolis (Cartwright & Cain, 1959a, b). However, from the growth characteristics and simultaneous adaptation experiments it appeared that 4-NOBA and 4-HABA but not 4-ABA or 4-HBA are intermediates in the degradation of 4-NBA by strain NBA-10.…”

Section: Discussionmentioning

confidence: 99%

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

Groenewegen

Breeuwer

Helvoort

et al. 1992

Journal of General Microbiology

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A Cornamonas acidooovans strain, designated NBA-10, was isolated on 4-nitrobenzoate as sole carbon and energy source. When grown on 4-nitrobenzoate, it was simultaneously adapted to 4-nitrosobenzoate and 4-hydroxylaminobenzoate but not to 4-hydroxybenzoate or 4-aminobenzoate. In cell extracts with NADPH present, 4-nitrobenzoate was degraded to 4-hydroxylaminobenzoate and 3,4-dihydroxybenzoate. Partial purification of the 4-nitrobenzoate reductase revealed that 4-nitrobenzoate is degraded via 4-nitrosobenzoate to 4-hydroxylaminobenzoate. The substrate specificity of the enzyme was narrow and NADPH was 15 times more effective as a cofactor than NADH. The results provide evidence for a novel pathway for aerobic degradation of 4-nitrobenzoate, since neither 4-hydroxybenzoate nor 4-aminobenzoate were involved in the degradative pathway.

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Section: Discussionmentioning

confidence: 99%

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

Groenewegen

Breeuwer

Helvoort

et al. 1992

Journal of General Microbiology

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“…Several strains of Nocardia were isolated by Cain et al in the late 1950s for their ability to use 2-, 3-, or 4-nitrobenzoate as the sole carbon, nitrogen, and energy source for growth, but the degradation pathways were not fully characterized (16,20). Analysis of more recently isolated strains has led to the identification of genes and enzymes for nitrobenzoate metabolism.…”

Section: Pathways For Nitrobenzoate and Nitrobenzaldehyde Catabolismmentioning

confidence: 99%

Nitroaromatic Compounds, from Synthesis to Biodegradation

Parales

2010

Microbiol Mol Biol Rev

775

470

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SUMMARY Nitroaromatic compounds are relatively rare in nature and have been introduced into the environment mainly by human activities. This important class of industrial chemicals is widely used in the synthesis of many diverse products, including dyes, polymers, pesticides, and explosives. Unfortunately, their extensive use has led to environmental contamination of soil and groundwater. The nitro group, which provides chemical and functional diversity in these molecules, also contributes to the recalcitrance of these compounds to biodegradation. The electron-withdrawing nature of the nitro group, in concert with the stability of the benzene ring, makes nitroaromatic compounds resistant to oxidative degradation. Recalcitrance is further compounded by their acute toxicity, mutagenicity, and easy reduction into carcinogenic aromatic amines. Nitroaromatic compounds are hazardous to human health and are registered on the U.S. Environmental Protection Agency's list of priority pollutants for environmental remediation. Although the majority of these compounds are synthetic in nature, microorganisms in contaminated environments have rapidly adapted to their presence by evolving new biodegradation pathways that take advantage of them as sources of carbon, nitrogen, and energy. This review provides an overview of the synthesis of both man-made and biogenic nitroaromatic compounds, the bacteria that have been identified to grow on and completely mineralize nitroaromatic compounds, and the pathways that are present in these strains. The possible evolutionary origins of the newly evolved pathways are also discussed.

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“…Because synthesis of new enzyme protein is an energy-requiring process some general inhibitors of energy-producing systems (dinitrophenols, azide, arsenate ; Monod, 1944;Reiner, 1946;Spiegelman, 1947;Monod & Cohn, 1952;Cohen & Monod, 1957) were examined for their effects upon anthranilate oxidase induction. Table 3.…”

Section: Inability Of Analogues To Ilzduce Afithrafiilate Oxidasementioning

confidence: 99%

“…Anthranilic acid: a t 240mp, e = 4505; at 268 mp, e = 310. Nocurdiu opaca did not reduce the aromatic nitro group of chloramphenicol (CartWright & Cain, 19593; and unpublished results) so the presence of this compound in culture media did not affect estimations of arylamines by the diazotization procedure.…”

Section: Introductionmentioning

confidence: 99%

“…In the absence of anthranilate oxidase, the reduction step (I) is the only known reaction which could occur when o-nitrobenzoic acid is the substrate. Energy considerations (reduction of the nitro group is NADH-mediated Saz & Slie, 1954; Cartwright & Cain, 19593; formation of NADH usually requires, not yields, energy) and molar growth yield experiments with anthranilic and onitrobenzoic acids as substrates (Cain, 1966) suggest that no energy is available from this reduction step. Since growth does occur in the normal absence of the anthranilate oxidase enzyme ( Fig.…”

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confidence: 99%

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Induction of an Anthranilate Oxidation System During the Metabolism of ortho-Nitrobenzoate by Certain Bacteria

Cain¹

1966

Journal of General Microbiology

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SUMMARYNocardia opaca, a flavobacterium and certain other bacteria, when grown on o-nitrobenzoate, accumulated anthranilate in the medium in the early stages of growth. The subsequent disappearance of this metabolite in growing cultures was always correlated with the appearance of an anthranilate oxidase system in the organisms. This phenomenon has the features of a typical enzyme adaptation except that the inducer is a byproduct of the cells' own metabolism; hence it has been termed 'metabolite induction '. The results confirm previous suggestions that, in these micro-organisms, anthranilate is not an obligatory intermediate in the direct energy-producing pathway of o-nitrobenzoate breakdown but is produced in a side reaction.

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Bacterial degradation of the nitrobenzoic acids

Cited by 90 publications

References 37 publications

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

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

Nitroaromatic Compounds, from Synthesis to Biodegradation

Induction of an Anthranilate Oxidation System During the Metabolism of ortho-Nitrobenzoate by Certain Bacteria

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