| 1392412-15-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪类
• CAS: 1392412-15-5
• 化学式: C₆H₉N₃O₄
• 分子量: 187.155
• InChiKey: QLFJYOWZWFLJIR-UHFFFAOYSA-N

反应信息

• 作为产物：
  描述：

  5,6-dihydro-1,3-dimethyl-5-nitrouracil 以 水 为溶剂， 以12 mg的产率得到
  参考文献：
  名称：

  Dehydrogenation, oxidative denitration and ring contraction of N,N-dimethyl-5-nitrouracil by a Bacillus nitroreductase Nfr-A1

  摘要：

  Nfr-A1, a Bacillus subtilis nitroreductase, catalyzes the nitroreduction of a large panel of aromatic and heterocyclic nitro compounds, except those belonging to nitrouracil class of molecules. Besides nitroreduction, Nfr-A1 exhibits a strong NADH oxidase activity in the presence of oxygen, leading to high concentration of H2O2 (up to 200 mu M). In the presence of (N,N)-dimethyl-5-nitrouracil 1 (dim-NU), Nfr-A1 achieves the reduction of dim-NU double bond to compounds 2 and 3 and in parallel the oxidation of dim-NU to the denitrated five membered derivatives 4 and 5. The reduction is catalyzed by the reduced Flavin Fl-(Red) and resembles those catalyzed by dihydropyrimidine clehydrogenases (DPD), during the catabolism of pyrimidines. The oxidative denitration is catalyzed in part by hydrogen peroxide generated through the NADH-oxidase activity, and certainly by the peroxyflavin intermediate Fl-(OOH) for the other part. The mechanisms of reaction were proposed according to experimental data and literature. These findings together with our previous results on the potential biological role of Nfr-A1, confirm the large spectrum of catalysis supported by this enzyme. The oxidative denitration is sporadically reported in literature and represents a safe and green alternative for the remediation of nitro-compounds. (C) 2011 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.molcatb.2011.11.014