title: 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.
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.
authors: Institut für Biochemie, Universität Witten/Herdecke, D-58453 Witten, Germany.
authors: C
authors: C
authors: Behrend
authors: K
authors: K
authors: Heesche-Wagner
mesh_terms: D019297:2,4-Dinitrophenol / Q000737:chemistry / Q000378:metabolism; D000192:Actinomycetales / Q000145:classification / Q000302:isolation & purification* / Q000378:metabolism*; D001673:Biodegradation, Environmental; D002851:Chromatography, High Pressure Liquid; D004275:DNA, Ribosomal / Q000235:genetics; D009682:Magnetic Resonance Spectroscopy; D010851:Picrates / Q000378:metabolism*; D012336:RNA, Ribosomal, 16S / Q000235:genetics; D012988:Soil Microbiology
chemical_list: D004275:DNA, Ribosomal; D010851:Picrates; D012336:RNA, Ribosomal, 16S; C005858:picric acid; D019297:2,4-Dinitrophenol