2'-deoxyuridine 5'-(α,β-imido)triphosphate

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 嘧啶核苷
• 英文名称: 2'-deoxyuridine 5'-(α,β-imido)triphosphate
• 英文别名: 2'-Deoxyuridine 5'-alpha,beta-imido-triphosphate；[(2R,3S,5R)-5-(2,4-dioxopyrimidin-1-yl)-3-hydroxyoxolan-2-yl]methoxy-N-[hydroxy(phosphonooxy)phosphoryl]phosphonamidic acid
• 化学式: C₉H₁₆N₃O₁₃P₃
• 分子量: 467.16
• InChiKey: XZLLMTSKYYYJLH-SHYZEUOFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -5.7
• 重原子数：
  28
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  242
• 氢给体数：
  7
• 氢受体数：
  14

反应信息

• 作为产物：
  描述：

  2'-deoxyuridine 5'-(α,β-imido)diphosphate triethylammonium salt 在 1,4-dithio-erythritol 、 磷烯醇丙酮酸 、 三羟甲基氨基甲烷盐酸盐 作用下， 反应 6.0h， 以92%的产率得到2'-deoxyuridine 5'-(α,β-imido)triphosphate
  参考文献：
  名称：

  Synthesis of 2′-deoxyuridine 5′-(α,β-imido)triphosphate: a substrate analogue and potent inhibitor of dUTPase

  摘要：

  The dUDP analogue, 2'-deoxyuridine 5'-(alpha,beta-imido)diphosphate (dUPNP) was synthesized. The corresponding triphosphate analogue (dUPNPP) was prepared by enzymic phosphorylation of dUPNP using the enzyme pyruvate kinase and phosphoenolpyruvate as the phosphate donor. This method was successful in phosphorylating the imidodiphosphate analogue of 2'-deoxythymidine (dTPNP) to 2'-deoxythymidine 5'-(alpha,beta-imido)triphosphate (dTPNPP), in contradiction to a previous report. The properties of dUPNPP have been tested using the enzyme dUTPase from Escherichia coli. This enzyme, having a crucial role in nucleotide metabolism, is strictly specific for its substrate (dUTP) and catalyzes the hydrolysis of the alpha,beta-bridge, resulting in dUMP and pyrophosphate. Replacement of the alpha,beta-bridging oxygen in dUTP with an imido group resulted in a nonhydrolyzable substrate analogue and a potent competitive inhibitor of dUTPase (K-i = 5 mu M). The analogue prepared (dUPNPP) may be utilized in crystallographic studies of the active site of dUTPase to provide knowledge about specific interactions involved in substrate binding and as a parental compound in design of dUTPase inhibition for medical purposes. Copyright (C) 1996 Elsevier Science Ltd

  DOI：

  10.1016/0968-0896(96)00044-2