Biotechnology Research Institute, National Research Council Canada, 6100 Royalmount Avenue, Montreal, Quebec, H4P 2R2, Canada.
Environ Sci Technol. 2012 Jun 5;46(11):6035-40. doi: 10.1021/es301047d. Epub 2012 May 17.
Nitroguanidine (NQ) is an energetic material that is used as a key ingredient of triple-base propellants and is currently being considered as a TNT replacement in explosive formulations. NQ was efficiently degraded in aerobic microcosms when a carbon source was added. NQ persisted in unamended microcosms or under anaerobic conditions. An aerobic NQ-degrading bacterium, Variovorax strain VC1, was isolated from soil microcosms containing NQ as the sole nitrogen source. NQ degradation was inhibited in the presence of a more favorable source of nitrogen. Resting cells of VC1 degraded NQ effectively (54 μmol h(-1) g(-1) protein) giving NH(3) (50.0%), nitrous oxide (N(2)O) (48.5%) and CO(2) (100%). Disappearance of NQ was accompanied by the formation of a key intermediate product that we identified as nitrourea by comparison with a reference material. Nitrourea is unstable in water and suffered both biotic and abiotic decomposition to eventually give NH(3), N(2)O, and CO(2). However, we were unable to detect urea. Based on products distribution and reaction stoichiometry, we suggested that degradation of NQ, O(2)NN═C(NH(2))(2), might involve initial enzymatic hydroxylation of the imine, -C═N- bond, leading first to the formation of the unstable α-hydroxynitroamine intermediate, O(2)NNHC(OH)(NH(2))(2), whose decomposition in water should lead to the formation of NH(3), N(2)O, and CO(2). NQ biodegradation was induced by nitroguanidine itself, L-arginine, and creatinine, all being iminic compounds containing a guanidine group. This first description of NQ mineralization by a bacterial isolate demonstrates the potential for efficient microbial remediation of NQ in soil.
硝胍(NQ)是一种高能材料,用作三基推进剂的关键成分,目前正被考虑作为爆炸制剂中 TNT 的替代品。当添加碳源时,NQ 在需氧微环境中能被高效降解。在未改良的微环境或厌氧条件下,NQ 则能持续存在。从含有 NQ 作为唯一氮源的土壤微环境中分离到一种好氧 NQ 降解菌,即 Variovorax 菌株 VC1。当存在更有利的氮源时,NQ 的降解会受到抑制。VC1 的休眠细胞能有效地降解 NQ(54 μmol h(-1) g(-1) protein),生成 NH(3)(50.0%)、氧化亚氮(N(2)O)(48.5%)和 CO(2)(100%)。NQ 的消失伴随着一种关键中间产物的形成,我们通过与参考物质比较将其鉴定为硝脲。硝脲在水中不稳定,会经历生物和非生物分解,最终生成 NH(3)、N(2)O 和 CO(2)。但是,我们无法检测到尿素。基于产物分布和反应计量学,我们提出 NQ、O(2)NN═C(NH(2))(2)的降解可能涉及最初的酶促亚胺化,-C═N-键的羟化,导致不稳定的α-羟基亚硝胺中间体 O(2)NNHC(OH)(NH(2))(2)的形成,其在水中的分解应导致 NH(3)、N(2)O 和 CO(2)的形成。NQ 生物降解由硝胍本身、L-精氨酸和肌酸诱导,这些都是含有胍基的亚氨基化合物。这是首次报道细菌分离物对 NQ 的矿化作用,证明了在土壤中有效微生物修复 NQ 的潜力。