1-α-D-ribofuranosyl-1H-pyrimidin-2-one | 65025-05-0

• 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: 1-α-D-ribofuranosyl-1H-pyrimidin-2-one
• CAS: 65025-05-0
• 化学式: C₉H₁₂N₂O₅
• 分子量: 228.205
• InChiKey: RPQZTTQVRYEKCR-XUTVFYLZSA-N

物化性质

• 沸点：
  499.0±55.0 °C(Predicted)
• 密度：
  1.73±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -2.15
• 重原子数：
  16.0
• 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：
  104.81
• 氢给体数：
  3.0
• 氢受体数：
  7.0

反应信息

• 作为产物：
  描述：

  2-羟基嘧啶 、 D-核糖 在 magnesium sulfate 、 magnesium chloride 作用下， 反应 2.25h， 以12%的产率得到4-脱氧尿苷
  参考文献：
  名称：

  Formation of a β-Pyrimidine Nucleoside by a Free Pyrimidine Base and Ribose in a Plausible Prebiotic Reaction

  摘要：

  The problem of beta-nucleoside formation under prebiotic conditions represents one of the most significant challenges to the RNA world hypothesis and to many of its proposed precursors. The possibility exists that alternative bases may have come before the contemporary bases (i.e., A, G, C, and U), including bases that more readily form nucleosides. In a search for pyrimidine bases that are able to form nucleosides in plausible prebiotic reactions, it was discovered that the drying and heating of 2-pyrimidinone with ribose produces a beta-furanosyl ribonucleoside in approximately 12% yield. At least two other chemical isomers of zebularine are also produced in the condensation reaction. This work represents the first successful synthesis of a pyrimidine nucleoside from a free base and a nonactivated sugar in a plausible prebiotic reaction. A comparison of 2-pyrimidinone with the purine bases that have also been demonstrated to form nucleosides in plausible prebiotic reactions provides insights regarding what chemical features of the bases facilitate glycoside formation in drying-heating reactions.

  DOI：

  10.1021/ja072781a

文献信息

• Formation of a β-Pyrimidine Nucleoside by a Free Pyrimidine Base and Ribose in a Plausible Prebiotic Reaction
  作者：Heather D. Bean、Yinghong Sheng、James P. Collins、Frank A. L. Anet、Jerzy Leszczynski、Nicholas V. Hud

  DOI：10.1021/ja072781a

  日期：2007.8.1

  The problem of beta-nucleoside formation under prebiotic conditions represents one of the most significant challenges to the RNA world hypothesis and to many of its proposed precursors. The possibility exists that alternative bases may have come before the contemporary bases (i.e., A, G, C, and U), including bases that more readily form nucleosides. In a search for pyrimidine bases that are able to form nucleosides in plausible prebiotic reactions, it was discovered that the drying and heating of 2-pyrimidinone with ribose produces a beta-furanosyl ribonucleoside in approximately 12% yield. At least two other chemical isomers of zebularine are also produced in the condensation reaction. This work represents the first successful synthesis of a pyrimidine nucleoside from a free base and a nonactivated sugar in a plausible prebiotic reaction. A comparison of 2-pyrimidinone with the purine bases that have also been demonstrated to form nucleosides in plausible prebiotic reactions provides insights regarding what chemical features of the bases facilitate glycoside formation in drying-heating reactions.