Uridine-5''-glucose-1''-tetraphosphate | 1047980-90-4

• 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: Uridine-5''-glucose-1''-tetraphosphate
• 英文别名: [[(2R,3S,4R,5R)-5-(2,4-dioxopyrimidin-1-yl)-3,4-dihydroxyoxolan-2-yl]methoxy-hydroxyphosphoryl] [hydroxy-[hydroxy-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyphosphoryl]oxyphosphoryl] hydrogen phosphate
• CAS: 1047980-90-4
• 化学式: C₁₅H₂₆N₂O₂₃P₄
• 分子量: 726.266
• InChiKey: AJLLTXOUJGYGAA-JZMIEXBBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -8.5
• 重原子数：
  44
• 可旋转键数：
  13
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.73
• 拓扑面积：
  385
• 氢给体数：
  11
• 氢受体数：
  23

反应信息

• 作为产物：
  描述：

  尿苷-5'-三磷酸 、 对氟苯甲醇 在 三正丁胺 、 N,N'-二环己基碳二亚胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 49.0h， 生成 Uridine-5''-glucose-1''-tetraphosphate
  参考文献：
  名称：

  Synthesis and potency of novel uracil nucleotides and derivatives as P2Y2 and P2Y6 receptor agonists

  摘要：

  The phosphate, uracil, and ribose moieties of uracil nucleotides were varied structurally for evaluation of agonist activity at the human P2Y(2), P2Y(4), and P2Y(6) receptors. The 2-thio modi. cation, found previously to enhance P2Y2 receptor potency, could be combined with other favorable modi. cations to produce novel molecules that exhibit high potencies and receptor selectivities. Phosphonomethylene bridges introduced for stability in analogues of UDP, UTP, and uracil dinucleotides markedly reduced potency. Truncation of dinucleotide agonists of the P2Y(2) receptor, in the form of Up(4)-sugars, indicated that a terminal uracil ring is not essential for moderate potency at this receptor and that specific SAR patterns are observed at this distal end of the molecule. Key compounds reported in this study include 9, alpha, beta-methylene-UDP, a P2Y(6) receptor agonist; 30, Up(4)-phenyl ester and 34, Up(4)-[1] glucose, selective P2Y(2) receptor agonists; dihalomethylene phosphonate analogues 16 and 41, selective P2Y(2) receptor agonists; 43, the 2-thio analogue of INS37217 (P-1-(uridine-5')-P-4-(2'-deoxycytidine-5') tetraphosphate), a potent and selective P2Y(2) receptor agonist. Published by Elsevier Ltd.

  DOI：

  10.1016/j.bmc.2008.05.013

文献信息

• Polyphosphate-containing bisubstrate analogues as inhibitors of a bacterial cell wall thymidylyltransferase
  作者：Deborah A. Smithen、Stephanie M. Forget、Nicole E. McCormick、Raymond T. Syvitski、David L. Jakeman

  DOI：10.1039/c4ob02583k

  日期：——

  The first synthesis and evaluation of bisubstrate analogues with a thymidylyltransferase is reported. WaterLOGSY NMR and kinetic analyses provide insight into bisubstrate analogue binding.

  报道了第一次合成和评价具有胸苷酸转移酶的双底物类似物。WaterLOGSY NMR和动力学分析提供了关于双底物类似物结合的见解。