Literature DB >> 10103224

Formation of hydride-Meisenheimer complexes of picric acid (2,4, 6-trinitrophenol) and 2,4-dinitrophenol during mineralization of picric acid by Nocardioides sp. strain CB 22-2.

C Behrend1, K Heesche-Wagner.   

Abstract

There are only a few examples of microbial conversion of picric acid (2,4,6-trinitrophenol). None of the organisms that have been described previously is able to use this compound as a sole source of carbon, nitrogen, and energy at high rates. In this study we isolated and characterized a strain, strain CB 22-2, that was able to use picric acid as a sole source of carbon and energy at concentrations up to 40 mM and at rates of 1.6 mmol. h(-1). g (dry weight) of cells(-1) in continuous cultures and 920 micromol. h(-1). g (dry weight) of cells(-1) in flasks. In addition, this strain was able to use picric acid as a sole source of nitrogen at comparable rates in a nitrogen-free medium. Biochemical characterization and 16S ribosomal DNA analysis revealed that strain CB 22-2 is a Nocardioides sp. strain. High-pressure liquid chromatography and UV-visible light data, the low residual chemical oxygen demand, and the stoichiometric release of 2.9 +/- 0.1 mol of nitrite per mol of picric acid provided strong evidence that complete mineralization of picric acid occurred. During transformation, the metabolites detected in the culture supernatant were the [H-]-Meisenheimer complexes of picric acid and 2,4-dinitrophenol (H--DNP), as well as 2,4-dinitrophenol. Experiments performed with crude extracts revealed that H--DNP formation indeed is a physiologically relevant step in picric acid metabolism.

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Year:  1999        PMID: 10103224      PMCID: PMC91194     

Source DB:  PubMed          Journal:  Appl Environ Microbiol        ISSN: 0099-2240            Impact factor:   4.792


  24 in total

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Journal:  Arch Microbiol       Date:  1990       Impact factor: 2.552

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Journal:  Biochem Biophys Res Commun       Date:  1979-05-28       Impact factor: 3.575

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Journal:  Eur J Biochem       Date:  1973-06

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Authors:  J Zeyer; H P Kocher
Journal:  J Bacteriol       Date:  1988-04       Impact factor: 3.490

5.  2,4-Dinitrotoluene dioxygenase from Burkholderia sp. strain DNT: similarity to naphthalene dioxygenase.

Authors:  W C Suen; B E Haigler; J C Spain
Journal:  J Bacteriol       Date:  1996-08       Impact factor: 3.490

6.  Mineralization of 2,4,6-trinitrophenol (picric acid): characterization and phylogenetic identification of microbial strains.

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Journal:  J Ind Microbiol       Date:  1996-05

7.  Effect of substrate and pH on the oxidative half-reaction of phenol hydroxylase.

Authors:  K Detmer; V Massey
Journal:  J Biol Chem       Date:  1985-05-25       Impact factor: 5.157

8.  Initial hydrogenation during catabolism of picric acid by Rhodococcus erythropolis HL 24-2.

Authors:  H Lenke; H J Knackmuss
Journal:  Appl Environ Microbiol       Date:  1992-09       Impact factor: 4.792

9.  Influence of para-substituents on the oxidative metabolism of o-nitrophenols by Pseudomonas putida B2.

Authors:  J Zeyer; H P Kocher; K N Timmis
Journal:  Appl Environ Microbiol       Date:  1986-08       Impact factor: 4.792

10.  Pseudomonas aeruginosa strain MA01 aerobically metabolizes the aminodinitrotoluenes produced by 2,4,6-trinitrotoluene nitro group reduction.

Authors:  M A Alvarez; C L Kitts; J L Botsford; P J Unkefer
Journal:  Can J Microbiol       Date:  1995-11       Impact factor: 2.419

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  13 in total

1.  Gas phase reactions of 1,3,5-triazine: proton transfer, hydride transfer, and anionic σ-adduct formation.

Authors:  John M Garver; Zhibo Yang; Shuji Kato; Scott W Wren; Kristen M Vogelhuber; W Carl Lineberger; Veronica M Bierbaum
Journal:  J Am Soc Mass Spectrom       Date:  2011-04-19       Impact factor: 3.109

Review 2.  Nitroaromatic compounds, from synthesis to biodegradation.

Authors:  Kou-San Ju; Rebecca E Parales
Journal:  Microbiol Mol Biol Rev       Date:  2010-06       Impact factor: 11.056

3.  Aerobic degradation of 2,4,6-trinitrophenol by Proteus sp. strain OSES2 obtained from an explosive contaminated tropical soil.

Authors:  Osekokhune E Okozide; Sunday A Adebusoye; Oluwafemi S Obayori; Deborah F Rodrigues
Journal:  Biodegradation       Date:  2021-09-06       Impact factor: 3.909

4.  Homologous npdGI genes in 2,4-dinitrophenol- and 4-nitrophenol-degrading Rhodococcus spp.

Authors:  Gesche Heiss; Natalie Trachtmann; Yoshikatsu Abe; Masahiro Takeo; Hans-Joachim Knackmuss
Journal:  Appl Environ Microbiol       Date:  2003-05       Impact factor: 4.792

5.  Aerobic biodegradation of 2,4,6-trinitrotoluene (TNT) by Bacillus cereus isolated from contaminated soil.

Authors:  H Aysun Mercimek; Sadık Dincer; Gulcihan Guzeldag; Aysenur Ozsavli; Fatih Matyar
Journal:  Microb Ecol       Date:  2013-05-29       Impact factor: 4.552

6.  Degradation of 2,4,6-Trinitrophenol (TNP) by Arthrobacter sp. HPC1223 Isolated from Effluent Treatment Plant.

Authors:  Asifa Qureshi; Atya Kapley; Hemant J Purohit
Journal:  Indian J Microbiol       Date:  2012-07-17       Impact factor: 2.461

7.  NpdR, a repressor involved in 2,4,6-trinitrophenol degradation in Rhodococcus opacus HL PM-1.

Authors:  Dang P Nga; Josef Altenbuchner; Gesche S Heiss
Journal:  J Bacteriol       Date:  2004-01       Impact factor: 3.490

Review 8.  Physiology, Biochemistry, and Applications of F420- and Fo-Dependent Redox Reactions.

Authors:  Chris Greening; F Hafna Ahmed; A Elaaf Mohamed; Brendon M Lee; Gunjan Pandey; Andrew C Warden; Colin Scott; John G Oakeshott; Matthew C Taylor; Colin J Jackson
Journal:  Microbiol Mol Biol Rev       Date:  2016-04-27       Impact factor: 11.056

9.  Nitrite elimination and hydrolytic ring cleavage in 2,4,6-trinitrophenol (picric acid) degradation.

Authors:  Klaus W Hofmann; Hans-Joachim Knackmuss; Gesche Heiss
Journal:  Appl Environ Microbiol       Date:  2004-05       Impact factor: 4.792

10.  Aerobic biodegradation of 2,4-Dinitroanisole by Nocardioides sp. strain JS1661.

Authors:  Tekle Tafese Fida; Shannu Palamuru; Gunjan Pandey; Jim C Spain
Journal:  Appl Environ Microbiol       Date:  2014-10-03       Impact factor: 4.792

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