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Applied and Environmental Microbiology, December 2001, p. 5460-5466, Vol. 67, No. 12
0099-2240/01/$04.00+0   DOI: 10.1128/AEM.67.12.5460-5466.2001
Copyright © 2001, American Society for Microbiology. All rights reserved.

Oxidative Transformation of Aminodinitrotoluene Isomers by Multicomponent Dioxygenases

Glenn R. Johnson,1 Barth F. Smets,2 and Jim C. Spain1,*

Air Force Research Laboratory, Tyndall Air Force Base, Florida,1 and Department of Civil and Environmental Engineering, University of Connecticut, Storrs, Connecticut2

Received 7 May 2001/Accepted 11 September 2001

The electron-withdrawing nitro substituents of 2,4,6-trinitrotoluene (TNT) make the aromatic ring highly resistant to oxidative transformation. The typical biological transformation of TNT involves reduction of one or more of the nitro groups of the ring to produce the corresponding amine. Reduction of a single nitro substituent of TNT to an amino substituent increases the electron density of the aromatic nucleus considerably. The comparatively electron-dense nuclei of the aminodinitrotoluene (ADNT) isomers would be expected to be more susceptible to oxygenase attack than TNT. The hypothesis was tested by evaluating three nitroarene dioxygenases for the ability to hydroxylate the ADNT isomers. The predominant reaction was dioxygenation of the ring to yield nitrite and the corresponding aminomethylnitrocatechol. A secondary reaction was benzylic monooxygenation to form aminodinitrobenzyl alcohol. The substrate preferences and catalytic specificities of the three enzymes differed considerably. The discovery that the ADNT isomers are substrates for the nitroarene dioxygenases reveals the potential for extensive bacterial transformation of TNT under aerobic conditions.

* Corresponding author. Mailing address: AFRL/MLQL, 139 Barnes Dr.-Suite 2, Tyndall AFB, FL 32403. Phone: (850) 283-6058. Fax: (850) 283-6223. E-mail: jim.spain{at}tyndall.af.mil.

Applied and Environmental Microbiology, December 2001, p. 5460-5466, Vol. 67, No. 12
0099-2240/01/$04.00+0   DOI: 10.1128/AEM.67.12.5460-5466.2001
Copyright © 2001, American Society for Microbiology. All rights reserved.


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Copyright © 2001 by the American Society for Microbiology. All rights reserved.