{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,10,3]],"date-time":"2026-10-03T07:29:43Z","timestamp":1791012583971,"version":"4.1.0"},"reference-count":21,"publisher":"American Society for Microbiology","issue":"3","license":[{"start":{"date-parts":[[2003,3,1]],"date-time":"2003-03-01T00:00:00Z","timestamp":1046476800000},"content-version":"tdm","delay-in-days":0,"URL":"https:\/\/journals.asm.org\/non-commercial-tdm-license"}],"content-domain":{"domain":["journals.asm.org"],"crossmark-restriction":true},"short-container-title":["Appl Environ Microbiol"],"published-print":{"date-parts":[[2003,3]]},"abstract":"<jats:title>ABSTRACT<\/jats:title>\n          <jats:p>\n            A unique metabolite with a molecular mass of 119 Da (C\n            <jats:sub>2<\/jats:sub>\n            H\n            <jats:sub>5<\/jats:sub>\n            N\n            <jats:sub>3<\/jats:sub>\n            O\n            <jats:sub>3<\/jats:sub>\n            ) accumulated during biotransformation of hexahydro-1,3,5-trinitro-1,3,5-triazine (RDX) by\n            <jats:italic>Rhodococcus<\/jats:italic>\n            sp. strain DN22 (D. Fournier, A. Halasz, J. C. Spain, P. Fiurasek, and J. Hawari, Appl. Environ. Microbiol. 68:166-172, 2002). The structure of the molecule and the reactions that led to its synthesis were not known. In the present study, we produced and purified the unknown metabolite by biotransformation of RDX with\n            <jats:italic>Rhodococcus<\/jats:italic>\n            sp. strain DN22 and identified the molecule as 4-nitro-2,4-diazabutanal using nuclear magnetic resonance and elemental analyses. Furthermore, we tested the hypothesis that a cytochrome P450 enzyme was responsible for RDX biotransformation by strain DN22. A cytochrome P450 2B4 from rabbit liver catalyzed a very similar biotransformation of RDX to 4-nitro-2,4-diazabutanal. Both the cytochrome P450 2B4 and intact cells of\n            <jats:italic>Rhodococcus<\/jats:italic>\n            sp. strain DN22 catalyzed the release of two nitrite ions from each reacted RDX molecule. A comparative study of cytochrome P450 2B4 and\n            <jats:italic>Rhodococcus<\/jats:italic>\n            sp. strain DN22 revealed substantial similarities in the product distribution and inhibition by cytochrome P450 inhibitors. The experimental evidence led us to propose that cytochrome P450 2B4 can catalyze two single electron transfers to RDX, thereby causing double denitration, which leads to spontaneous hydrolytic ring cleavage and decomposition to produce 4-nitro-2,4-diazabutanal. Our results provide strong evidence that a cytochrome P450 enzyme is the key enzyme responsible for RDX biotransformation by\n            <jats:italic>Rhodococcus<\/jats:italic>\n            sp. strain DN22.\n          <\/jats:p>","DOI":"10.1128\/aem.69.3.1347-1351.2003","type":"journal-article","created":{"date-parts":[[2003,3,6]],"date-time":"2003-03-06T01:03:44Z","timestamp":1046912624000},"page":"1347-1351","update-policy":"https:\/\/doi.org\/10.1128\/asmj-crossmark-policy-page","source":"Crossref","is-referenced-by-count":94,"title":["Biotransformation of Hexahydro-1,3,5-Trinitro-1,3,5-Triazine (RDX) by a Rabbit Liver Cytochrome P450: Insight into the Mechanism of RDX Biodegradation by\n            <i>Rhodococcus<\/i>\n            sp. Strain DN22"],"prefix":"10.1128","volume":"69","author":[{"given":"Bharat","family":"Bhushan","sequence":"first","affiliation":[{"name":"Biotechnology Research Institute, National Research Council of Canada, Montreal, Quebec H4P 2R2, Canada"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Sandra","family":"Trott","sequence":"additional","affiliation":[{"name":"U.S. Air Force Research Laboratory, Tyndall Air Force Base, Florida 32403"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Jim C.","family":"Spain","sequence":"additional","affiliation":[{"name":"U.S. Air Force Research Laboratory, Tyndall Air Force Base, Florida 32403"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Annamaria","family":"Halasz","sequence":"additional","affiliation":[{"name":"Biotechnology Research Institute, National Research Council of Canada, Montreal, Quebec H4P 2R2, Canada"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Louise","family":"Paquet","sequence":"additional","affiliation":[{"name":"Biotechnology Research Institute, National Research Council of Canada, Montreal, Quebec H4P 2R2, Canada"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Jalal","family":"Hawari","sequence":"additional","affiliation":[{"name":"Biotechnology Research Institute, National Research Council of Canada, Montreal, Quebec H4P 2R2, Canada"}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"235","reference":[{"key":"e_1_3_2_2_2","doi-asserted-by":"publisher","DOI":"10.1021\/es011460a"},{"key":"e_1_3_2_3_2","doi-asserted-by":"publisher","DOI":"10.1128\/aem.61.4.1318-1322.1995"},{"key":"e_1_3_2_4_2","doi-asserted-by":"publisher","DOI":"10.1016\/S0038-0717(97)00172-7"},{"key":"e_1_3_2_5_2","doi-asserted-by":"publisher","DOI":"10.1046\/j.1365-2672.2002.01713.x"},{"key":"e_1_3_2_6_2","doi-asserted-by":"publisher","DOI":"10.1128\/AEM.68.1.166-172.2002"},{"key":"e_1_3_2_7_2","doi-asserted-by":"publisher","DOI":"10.1021\/tx0002583"},{"key":"e_1_3_2_8_2","doi-asserted-by":"publisher","DOI":"10.1007\/BF00322782"},{"key":"e_1_3_2_9_2","doi-asserted-by":"publisher","DOI":"10.1021\/es011071g"},{"key":"e_1_3_2_10_2","doi-asserted-by":"crossref","unstructured":"Hawari J. 2000. Biodegradation of RDX and HMX: from basic research to field application p. 277-310. In J. C. Spain J. B. Hughes and H.-J. Knackmuss (ed.) Biodegradation of nitroaromatic compounds and explosives. CRC Press Boca Raton Fla.","DOI":"10.1201\/9781420032673.ch11"},{"key":"e_1_3_2_11_2","doi-asserted-by":"publisher","DOI":"10.1128\/AEM.66.6.2652-2657.2000"},{"key":"e_1_3_2_12_2","doi-asserted-by":"publisher","DOI":"10.1128\/jb.175.5.1467-1474.1993"},{"key":"e_1_3_2_13_2","doi-asserted-by":"publisher","DOI":"10.1139\/w99-134"},{"key":"e_1_3_2_14_2","doi-asserted-by":"publisher","DOI":"10.1128\/aem.42.5.817-823.1981"},{"key":"e_1_3_2_15_2","doi-asserted-by":"crossref","unstructured":"Myler C. A. and W. Sisk. 1991. Bioremediation of explosives contaminated soils (scientific questions\/ engineering realities) p. 137-146. In G. S. Sayler R. Fox and J. W. Blackburn (ed.) Environmental bio\/technology for waste treatment. Plenum Press New York N.Y.","DOI":"10.1007\/978-1-4684-5955-5_13"},{"key":"e_1_3_2_16_2","doi-asserted-by":"publisher","DOI":"10.1021\/es010852e"},{"key":"e_1_3_2_17_2","doi-asserted-by":"crossref","unstructured":"Ortiz de Montellano P. R. and M. A. Correia. 1995. Inhibition of cytochrome P450 enzymes p. 305-366. In P. R. Ortiz de Montellano (ed.) Cytochrome P450: structure mechanism and biochemistry 2nd ed. Plenum Press New York N.Y.","DOI":"10.1007\/978-1-4757-2391-5_9"},{"key":"e_1_3_2_18_2","doi-asserted-by":"publisher","DOI":"10.1111\/j.1365-2672.1969.tb00981.x"},{"key":"e_1_3_2_19_2","doi-asserted-by":"publisher","DOI":"10.1128\/AEM.68.10.4764-4771.2002"},{"key":"e_1_3_2_20_2","first-page":"1","volume":"161","year":"1999","unstructured":"Talmage, S. S., D. M. Opresko, C. J. Maxwel, C. J. E. Welsh, F. M. Cretella, P. H. Reno, and F. B. Daniel. 1999. Nitroaromatic munition compounds: environment effects and screening values. Rev. Environ. Contam. Toxicol.161:1-156.","journal-title":"Rev. Environ. Contam. 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