Biodegradation of 2,4,6-trinitrotoluene: Strategies for the Selection of Novel Catabolic Potential
2006
Knackmuss, Hans-Joachim
Polynitrophenols were used as model compounds for the metabolism of 2,4,6-trinitrotoluene. Oxidative as well as reductive initial reactions were observed during catabolism of polynitrophenols. The elimination of nitrite by an oxygenolytic mechanism was demonstrated with 2,6-dinitrophenol whereas 2,4- dinitrophenol or picric acid were subject to a nucleophilic reductive attack. The formation of a hydride-Meisenheimer complex followed by an elimination of nitrite leading to 2,4-dinitrophenol was also observed in cell-free systems. 2, 4,6-trinitrotoluene was subject to a nucleophilic attack by a hydride ion leading to a Meisenheimer complex as the initial metabolite. The hydride- Meisenheimer complex of 2,4,6-trinitrotoluene was synthesized chemically as a reference and identified by spectroscopic methods. In an anaerobic sludge supplemented with glucose and ammonia all nitro groups of 2,4,6-trinitrotoluene were reduced completely leading to 2,4,6-triaminotoluene which seemed to be further transformed under anaerobic conditions.
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