[(3aR,4R,6R,6aR)-4-[5-[[[(2R,3R,4R,5R)-2-(2,4-dioxopyrimidin-1-yl)-4-hydroxy-5-(hydroxymethyl)oxolan-3-yl]oxycarbonylamino]methyl]-2,4-dioxopyrimidin-1-yl]-2,2-dimethyl-3a,4,6,6a-tetrahydrofuro[3,4-d][1,3]dioxol-6-yl]methyl acetate | 202533-76-4

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 嘧啶核苷
• 英文名称: [(3aR,4R,6R,6aR)-4-[5-[[[(2R,3R,4R,5R)-2-(2,4-dioxopyrimidin-1-yl)-4-hydroxy-5-(hydroxymethyl)oxolan-3-yl]oxycarbonylamino]methyl]-2,4-dioxopyrimidin-1-yl]-2,2-dimethyl-3a,4,6,6a-tetrahydrofuro[3,4-d][1,3]dioxol-6-yl]methyl acetate
• CAS: 202533-76-4
• 化学式: C₂₅H₃₁N₅O₁₄
• 分子量: 625.546
• InChiKey: UJVQIABFSSOYNV-VFANGFAISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -2.5
• 重原子数：
  44
• 可旋转键数：
  10
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  241
• 氢给体数：
  5
• 氢受体数：
  14

反应信息

• 作为反应物：
  描述：

  [(3aR,4R,6R,6aR)-4-[5-[[[(2R,3R,4R,5R)-2-(2,4-dioxopyrimidin-1-yl)-4-hydroxy-5-(hydroxymethyl)oxolan-3-yl]oxycarbonylamino]methyl]-2,4-dioxopyrimidin-1-yl]-2,2-dimethyl-3a,4,6,6a-tetrahydrofuro[3,4-d][1,3]dioxol-6-yl]methyl acetate 在 四氮唑 、 氢氧化钾 、 三甲基氯硅烷 、 甲酸 、 三丁基氧化锡 、 氨苯砜 作用下， 以 吡啶 为溶剂， 反应 31.84h， 生成
  参考文献：
  名称：

  Chemical Synthesis and Properties of Conformationally Fixed Diuridine Monophosphates as Building Blocks of the RNA Turn Motif

  摘要：

  Two intramolecularly cyclized diuridine monophosphates having an amide and a carbamate linker have been synthesized for fixation of the LT-turn structure found in various tRNAs and hammerhead ribozymes. The structural analysis of these cyclic dimers using CD, H-1 NMR, and P-31 NMR spectroscopy shows that they have ri,sid, unstacked conformations. Detailed computer simulations of their 3D structures based on molecular mechanics calculations suggest that a two-state equilibrium between a stretch and a turn conformation exists in favor of the former. The simulation also suggested that the diuridine mono-phosphate containing the carbamate-linker is better as a mimic of the U-turn structure than the amide-linked dimer. The enzymatic properties of these cyclized dimers are also described.

  DOI：

  10.1021/jo971797o
• 作为产物：
  描述：

  [(3aR,4R,6R,6aR)-4-[5-[[[(6aR,8R,9R,9aR)-8-(2,4-dioxopyrimidin-1-yl)-2,2,4,4-tetra(propan-2-yl)-6a,8,9,9a-tetrahydro-6H-furo[3,2-f][1,3,5,2,4]trioxadisilocin-9-yl]oxycarbonylamino]methyl]-2,4-dioxopyrimidin-1-yl]-2,2-dimethyl-3a,4,6,6a-tetrahydrofuro[3,4-d][1,3]dioxol-6-yl]methyl acetate 在 四丁基氟化铵 、 溶剂黄146 作用下， 以 四氢呋喃 为溶剂， 反应 0.67h， 以96%的产率得到[(3aR,4R,6R,6aR)-4-[5-[[[(2R,3R,4R,5R)-2-(2,4-dioxopyrimidin-1-yl)-4-hydroxy-5-(hydroxymethyl)oxolan-3-yl]oxycarbonylamino]methyl]-2,4-dioxopyrimidin-1-yl]-2,2-dimethyl-3a,4,6,6a-tetrahydrofuro[3,4-d][1,3]dioxol-6-yl]methyl acetate
  参考文献：
  名称：

  Chemical Synthesis and Properties of Conformationally Fixed Diuridine Monophosphates as Building Blocks of the RNA Turn Motif

  摘要：

  Two intramolecularly cyclized diuridine monophosphates having an amide and a carbamate linker have been synthesized for fixation of the LT-turn structure found in various tRNAs and hammerhead ribozymes. The structural analysis of these cyclic dimers using CD, H-1 NMR, and P-31 NMR spectroscopy shows that they have ri,sid, unstacked conformations. Detailed computer simulations of their 3D structures based on molecular mechanics calculations suggest that a two-state equilibrium between a stretch and a turn conformation exists in favor of the former. The simulation also suggested that the diuridine mono-phosphate containing the carbamate-linker is better as a mimic of the U-turn structure than the amide-linked dimer. The enzymatic properties of these cyclized dimers are also described.

  DOI：

  10.1021/jo971797o