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PMID:8195105
| Citation |
Haigler, BE, Nishino, SF and Spain, JC (1994) Biodegradation of 4-methyl-5-nitrocatechol by Pseudomonas sp. strain DNT. J. Bacteriol. 176:3433-7 |
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| Abstract |
Pseudomonas sp. strain DNT degrades 2,4-dinitrotoluene (DNT) by a dioxygenase attack at the 4,5 position with concomitant removal of the nitro group to yield 4-methyl-5-nitrocatechol (MNC). Here we describe the mechanism of removal of the nitro group from MNC and subsequent reactions leading to ring fission. Washed suspensions of DNT-grown cells oxidized MNC and 2,4,5-trihydroxytoluene (THT). Extracts prepared from DNT-induced cells catalyzed the disappearance of MNC in the presence of oxygen and NADPH. Partially purified MNC oxygenase oxidized MNC in a reaction requiring 1 mol of NADPH and 1 mol of oxygen per mol of substrate. The enzyme converted MNC to 2-hydroxy-5-methylquinone (HMQ), which was identified by gas chromatography-mass spectrometry. HMQ was also detected transiently in culture fluids of cells grown on DNT. A quinone reductase was partially purified and shown to convert HMQ to THT in a reaction requiring NADH. A partially purified THT oxygenase catalyzed ring fission of THT and accumulation of a compound tentatively identified as 3-hydroxy-5-(1-formylethylidene)-2-furanone. Preliminary results indicate that this compound is an artifact of the isolation procedure and suggest that 2,4-dihydroxy-5-methyl-6-oxo-2,4-hexadienoic acid is the actual ring fission product. |
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| Keywords |
Biodegradation, Environmental; Catechols/metabolism; Dinitrobenzenes/metabolism; Fatty Acids, Unsaturated/metabolism; Mass Spectrometry; Models, Biological; NAD(P)H Dehydrogenase (Quinone)/isolation & purification; NADP/metabolism; Oxidation-Reduction; Oxygen/metabolism; Pseudomonas/enzymology; Pseudomonas/metabolism; Quinones/metabolism; Toluene/analogs & derivatives; Toluene/metabolism |
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