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Applied and Environmental Microbiology, January 2002, p. 166-172, Vol. 68, No. 1
0099-2240/02/$04.00+0     DOI: 10.1128/AEM.68.1.166-172.2002
Copyright © 2002, American Society for Microbiology. All Rights Reserved.

Determination of Key Metabolites during Biodegradation of Hexahydro-1,3,5-Trinitro-1,3,5-Triazine with Rhodococcus sp. Strain DN22{dagger}

Diane Fournier,1 Annamaria Halasz,1 Jim Spain,2 Petr Fiurasek,1 and Jalal Hawari1*

Biotechnology Research Institute, National Research Council of Canada, Montreal (Quebec) H4P 2R2, Canada,1 United States Air Force Research Laboratory, Tyndall Air Force Base, Panama City, Florida 324032

Received 17 August 2001/ Accepted 25 August 2001

Rhodococcus sp. strain DN22 can convert hexahydro-1,3,5-trinitro-1,3,5-triazine (RDX) to nitrite, but information on degradation products or the fate of carbon is not known. The present study describes aerobic biodegradation of RDX (175 µM) when used as an N source for strain DN22. RDX was converted to nitrite (NO2–) (30%), nitrous oxide (N2O) (3.2%), ammonia (10%), and formaldehyde (HCHO) (27%), which later converted to carbon dioxide. In experiments with ring-labeled [15N]-RDX, gas chromatographic/mass spectrophotometric (GC/MS) analysis revealed N2O with two molecular mass ions: one at 44 Da, corresponding to 14N14NO, and the second at 45 Da, corresponding to 15N14NO. The nonlabeled N2O could be formed only from -NO2, whereas the 15N-labeled one was presumed to originate from a nitramine group (15N-14NO2) in RDX. Liquid chromatographic (LC)-MS electrospray analyses indicated the formation of a dead end product with a deprotonated molecular mass ion [M-H] at 118 Da. High-resolution MS indicated a molecular formula of C2H5N3O3. When the experiment was repeated with ring-labeled [15N]-RDX, the [M-H] appeared at 120 Da, indicating that two of the three N atoms in the metabolite originated from the ring in RDX. When [U-14C]-RDX was used in the experiment, 64% of the original radioactivity in RDX incorporated into the metabolite with a molecular weight (MW) of 119 (high-pressure LC/radioactivity) and 30% in 14CO2 (mineralization) after 4 days of incubation, suggesting that one of the carbon atoms in RDX was converted to CO2 and the other two were incorporated in the ring cleavage product with an MW of 119. Based on the above stoichiometry, we propose a degradation pathway for RDX based on initial denitration followed by ring cleavage to formaldehyde and the dead end product with an MW of 119.

* Corresponding author. Mailing address: Biotechnology Research Institute, National Research Council of Canada, 6100 Royalmount Ave., Montreal (Quebec) H4P 2R2, Canada. Phone: (514) 496-6267. Fax: (514) 496-6265. E-mail: jalal.hawari{at}nrc.ca.

{dagger} This is NRCC publication number 44634.

Applied and Environmental Microbiology, January 2002, p. 166-172, Vol. 68, No. 1
0099-2240/02/$04.00+0     DOI: 10.1128/AEM.68.1.166-172.2002
Copyright © 2002, American Society for Microbiology. All Rights Reserved.



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