3',5'-diacetyl-O⁴-bicyclo[2.2.1]hept-5-en-2-ylmethylthymidine | 1235478-80-4

• 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: 3',5'-diacetyl-O⁴-bicyclo[2.2.1]hept-5-en-2-ylmethylthymidine
• 英文别名: 3',5'-di-O-acetyl-O4-(bicyclo[2.2.1]hept-5-en-2-ylmethyl)thymidine
• CAS: 1235478-80-4
• 化学式: C₂₂H₂₈N₂O₇
• 分子量: 432.474
• InChiKey: MICOQQBNSPRARB-GZGCJKLESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.93
• 重原子数：
  31.0
• 可旋转键数：
  7.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.64
• 拓扑面积：
  105.95
• 氢给体数：
  0.0
• 氢受体数：
  9.0

反应信息

• 作为反应物：
  描述：

  3',5'-diacetyl-O⁴-bicyclo[2.2.1]hept-5-en-2-ylmethylthymidine 在 氨 作用下， 以 甲醇 、 水 为溶剂， 反应 2.5h， 以74%的产率得到
  参考文献：
  名称：

  POST-SYNTHETIC MODIFICATION OF NUCLEIC ACIDS BY INVERSE DIELS-ALDER REACTION

  摘要：

  本发明涉及一种通过反向Diels-Alder反应对核酸进行后合成修饰的方法和试剂盒。

  公开号：

  US20130085271A1
• 作为产物：
  描述：

  3,5-双-O-乙酰胸苷 、 5-降冰片烯-2-甲醇 在 4-二甲氨基吡啶 、 三乙胺 作用下， 以 乙腈 为溶剂， 反应 14.0h， 生成 3',5'-diacetyl-O⁴-bicyclo[2.2.1]hept-5-en-2-ylmethylthymidine 、 3',5'-diacetyl-O⁴-bicyclo[2.2.1]hept-5-en-2-ylmethylthymidine
  参考文献：
  名称：

  Post-Synthetic Modification of DNA by Inverse-Electron-Demand Diels−Alder Reaction

  摘要：

  There is currently a tremendous interest in developing bioorthogonal "click chemistry" methods for the modification of biopolymers. Very recently, inverse-electron-demand Diels-Alder reactions have received attention, but to date they have not been applied to nucleic acids. Here we describe the first example of DNA modification by inverse-electron-demand Diets-Alder reaction. We synthesized four different building blocks for 3'-terminal, 5'-terminal, and internal incorporation of norbornene dienophiles into oligonucleotides. These DNA strands were either directly reacted with suitably derivatized tetrazine dienes or first subjected to enzymatic manipulations. We demonstrate that the inverse-electron-demand Diets-Alder reaction allows efficient site-specific post-synthetic conjugation, often at a 1:1 stoichiometry, without any side reaction. The reaction works in aqueous media at room temperature, and no transition metals are required. Both short chemically synthesized oligonucleotides and long enzymatically amplified DNA strands were successfully conjugated.

  DOI：

  10.1021/ja102871p