Structure of a laccase-mediated product of coupling of 2,4-diamino-6-nitrotoluene to guaiacol, a model for coupling of 2,4,6-trinitrotoluene metabolites to a humic organic soil matrix.

Applied and Environmental Microbiology
G DawelW Fritsche

Abstract

This work presents laccase-mediated model reactions for coupling of reduced 2,4,6-trinitrotoluene (TNT) metabolites to an organic soil matrix. The structure of an isolated coupling product of 2,4-diamino-6-nitrotoluene (2,4-DANT) to guaiacol as humic constituent was determined. Among several structures, the compound was identified conclusively to be the trinuclear coupling product 5-(2-amino-3-methyl-4-nitroanilino)-3,3(prm1)-dimethoxy-4,4(prm1)-diphenoqu inone. The compound has a weight of 409 g mol(sup-1) and may serve as a model reaction for the biogenic formation of bound residues in soil from TNT by coupling aminotoluenes (reduced TNT metabolites) to humic constituents. A linear correlation of the substrate consumption to the enzyme activity was detected. Based on this observation, the described reaction of 2,4-DANT coupling to guaiacol may be used for determination of laccase activity since the reaction was not inhibited by other compounds of culture supernatants. We propose a two-step mechanism for the coupling reaction because 2,4-DANT was not transformed by laccases in the absence of guaiacol and guaiacol oxidation was independent of the presence of 2,4-DANT. The first reaction step is a laccase-mediated dimerization o...Continue Reading

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Citations

Aug 31, 2001·Microbiology and Molecular Biology Reviews : MMBR·A Esteve-NúñezJ L Ramos
Feb 14, 2006·FEMS Microbiology Reviews·Petr Baldrian
Sep 4, 2001·Biotechnology & Genetic Engineering Reviews·C E FrenchN C Bruce
Jan 16, 2015·Environmental Science. Processes & Impacts·Ram Chandra, Pankaj Chowdhary
Nov 20, 2020·The Science of the Total Environment·Ann-Katrin LuksAndreas Schäffer
May 18, 2010·Biotechnology Advances·Ana I Cañas, Susana Camarero

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