[1'-3H]UMP | 1345203-06-6

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 嘧啶核苷酸
• 英文名称: [1'-3H]UMP
• CAS: 1345203-06-6
• 化学式: C₉H₁₃N₂O₉P
• 分子量: 326.176
• InChiKey: DJJCXFVJDGTHFX-DBPYKHNMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -2.73
• 重原子数：
  21.0
• 可旋转键数：
  4.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  171.31
• 氢给体数：
  5.0
• 氢受体数：
  8.0

反应信息

• 作为产物：
  描述：

  D-[1-3H]ribose 、 2,6-二氧代-3H-嘧啶-4-羧酸酯 在 potassium dihydrogenphosphate 、 pyruvate kinase 、 肌激酶 、 ribokinase 、 phosphoribosyl-α-1-pyrophosphate synthetase 、 UMP synthase 、 potassium chloride 、 2-(膦酰氧基)丙烯酸酯 、 5’-三磷酸腺苷 、 magnesium chloride 作用下， 以 水 为溶剂， 生成 [1'-3H]UMP
  参考文献：
  名称：

  Transition-State Analysis of Trypanosoma cruzi Uridine Phosphorylase-Catalyzed Arsenolysis of Uridine

  摘要：

  Uridine phosphorylase catalyzes the reversible phosphorolysis of uridine and 2'-deoxyuridine to generate uracil and (2-deoxy)ribose 1-phosphate, an important step in the pyrimidine salvage pathway. The coding sequence annotated as a putative nucleoside phosphorylase in the Ttypanosoma cruzi genome was overexpressed in Escherichia coli, purified to homogeneity, and shown to be a homoclimeric uridine phosphorylase, with similar specificity for uridine and 2'-deoxyuridine and undetectable activity toward thymidine and purine nucleosides. Competitive kinetic isotope effects (KIEs) were measured and corrected for a forward commitment factor using arsenate as the nucleophile. The intrinsic KIEs are: 1'-C-14 = 1.103, 1,3-N-15(2) = 1.034, 3-N-15 = 1.004, 1-N-15 = 1.030, 1'-3H = 1.132, 2'-H-2 = 1.086, and 5'-H-3(2) = 1.041 for this reaction. Density functional theory was employed to quantitatively interpret the KIEs in terms of transition-state structure and geometry. Matching of experimental KIEs to proposed transition-state structures suggests an almost synchronous, S(N)2-like transition-state model, in which the ribosyl moiety possesses significant bond order to both nucleophile and leaving groups. Natural bond orbital analysis allowed a comparison of the charge distribution pattern between the ground-state and the transition-state models.

  DOI：

  10.1021/ja2031294