Dr. Noguera et Dl. Freedman, REDUCTION AND ACETYLATION OF 2,4-DINITROTOLUENE BY A PSEUDOMONAS-AERUGINOSA STRAIN, Applied and environmental microbiology, 62(7), 1996, pp. 2257-2263
Aerobic and anoxic biotransformation of 2,4-dinitrotoluene (DNT) was e
xamined by using a Pseudomonas aeruginosa strain isolated from a plant
treating propellant manufacturing wastewater. DNT biotransformation i
n the presence and absence of oxygen was mostly reductive and was repr
esentative of the type of cometabolic transformations that occur when
a high concentration of an easily degradable carbon source is present.
P. aeruginosa reduced both nitro groups on DNT, with the formation of
mainly 4-amino-2-nitrotoluene and 2-amino-4-nitrotoluene and small qu
antities of 2,4-diaminotoluene. Acetylation of the arylamines was a si
gnificant reaction. 4-Acetamide-2-nitrotoluene and the novel compounds
2-acetamide-4-nitrotoluene, 4-acetamide-2-aminotoluene, and 2,4-diace
tamidetoluene were identified as DNT metabolites. The biotransformatio
n of 2,4-diaminotoluene to 4-acetamide-2-aminotoluene was 24 times fas
ter than abiotic transformation. 2-Nitrotoluene and 4-nitrotoluene wer
e also reduced to their corresponding toluidines and then acetylated.
However, the yield of 4-acetamidetoluene was much higher than that of
2-acetamidetoluene, demonstrating that acetylation at the position par
a to the methyl group was favored.