1-(β-D-2'-deoxyribofuranosyl)-4-pyrimidinone | 37109-98-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 1-(β-D-2'-deoxyribofuranosyl)-4-pyrimidinone
• 英文别名: 1-[(2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]pyrimidin-4-one
• CAS: 37109-98-1
• 化学式: C₉H₁₂N₂O₄
• 分子量: 212.205
• InChiKey: ZUPZBNPYYJNJPQ-LKEWCRSYSA-N

物化性质

• 沸点：
  450.2±55.0 °C(Predicted)
• 密度：
  1.57±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -1.12
• 重原子数：
  15.0
• 可旋转键数：
  2.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  84.58
• 氢给体数：
  2.0
• 氢受体数：
  6.0

反应信息

• 作为产物：
  描述：

  3',5'-di-O-(p-toluoyl)-1-(β-D-2'-deoxyribofuranosyl)-4-pyrimidinone 在 sodium methylate 作用下， 以 甲醇 为溶剂， 反应 0.5h， 以91%的产率得到1-(β-D-2'-deoxyribofuranosyl)-4-pyrimidinone
  参考文献：
  名称：

  Desulfurization of 2-thiouracil nucleosides: Conformational studies of 4-pyrimidinone nucleosides

  摘要：

  4-Pyrimidinone ribofuranoside (H(2)o(4)U) and 4-pyrimidinone 2 '-deoxyribofuranoside (dH(2)o(4)U) were synthesized by the oxidative desulfurization of parent 2-thiouracil nucleosides with m-chloroperbenzoic acid. The crystal structures of H(2)o(4)U and dH(2)o(4)U and their conformations in solution were determined and compared with corresponding 2-thiouracil and uracil nucleosides. The absence of a large 2-thiocarbonyl/2-carbonyl group in the nucleobase moiety results in C2'-endo puckering of the ribofuranose ring (S conformer) in the crystal structure of H(2)o(4)U, which is not typical of RNA nucleosides. Interestingly, the hydrogen bonding network in the crystals of dH(2)o(4)U stabilizes the sugar moiety conformation in the C3'-endo form (N conformer), rarely found in DNA nucleosides. In aqueous solution, dH(2)o(4)U reveals a similar population of the C2'-endo conformation (65%) to that of 2'-deoxy-2-thiouridine (62%), while the 62% population of the S conformer for H(2)o(4)U is significantly different from that of the parent 2-thiouridine, for which the N conformer is dominant (71%). Such a difference may be of biological importance, as the desulfurization process of natural tRNA 2-thiouridines may occur under conditions of oxidative stress in the cell and may influence the decoding process. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2011.02.008