3',5'-bis(t-butyl-dimethylsilyl)-5-[1,2-dihydroxy-2-(3,4,5-trimethoxyphenyl)-ethyl]-2'-deoxyuridine | 927683-60-1

• 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'-bis(t-butyl-dimethylsilyl)-5-[1,2-dihydroxy-2-(3,4,5-trimethoxyphenyl)-ethyl]-2'-deoxyuridine
• CAS: 927683-60-1
• 化学式: C₃₂H₅₄N₂O₁₀Si₂
• 分子量: 682.959
• InChiKey: JSJDZOTZNXVSGC-WENWTBRCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.03
• 重原子数：
  46.0
• 可旋转键数：
  12.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.69
• 拓扑面积：
  150.7
• 氢给体数：
  3.0
• 氢受体数：
  11.0

反应信息

• 作为反应物：
  描述：

  3',5'-bis(t-butyl-dimethylsilyl)-5-[1,2-dihydroxy-2-(3,4,5-trimethoxyphenyl)-ethyl]-2'-deoxyuridine 在 四丁基氟化铵 作用下， 以 四氢呋喃 、 吡啶 为溶剂， 反应 32.0h， 生成 5-[1,2-diacetoxy-2-(3,4,5-trimethoxyphenyl)-ethyl]-2'-deoxyuridine
  参考文献：
  名称：

  Hole Migration is the Major Pathway Involved in Alkali-Labile Lesion Formation in DNA by the Direct Effect of Ionizing Radiation

  摘要：

  Electron transfer via nucleobase hole migration has been extensively studied in recent years. Holes are produced in DNA via the direct effect of gamma-radiolysis. However, the contribution of this pathway to DNA damage is difficult to discern because common products are formed via the direct and indirect (e.g., hydroxyl radical) pathways. A molecular probe (1) was designed that serves as a repository for holes in DNA. Upon one-electron oxidation, 1 fragments to fdU, which is an alkali-labile lesion. Incorporation of 1 in synthetic DNA enables one to determine the contribution of hole transfer to DNA damage by gamma-radiolysis. We find that hole migration is the predominant pathway for alkali-labile lesion formation when DNA is exposed to Cs-137 in solution.

  DOI：

  10.1021/ja0678931
• 作为产物：
  描述：

  5-(1-(3,4,5-trimethoxyphenyl)-vinyl)-2'-deoxyuridine 在 咪唑 、 四氧化锇 、 N-甲基吲哚酮 作用下， 以 水 、 N,N-二甲基甲酰胺 、 丙酮 为溶剂， 反应 33.0h， 生成 3',5'-bis(t-butyl-dimethylsilyl)-5-[1,2-dihydroxy-2-(3,4,5-trimethoxyphenyl)-ethyl]-2'-deoxyuridine
  参考文献：
  名称：

  Hole Migration is the Major Pathway Involved in Alkali-Labile Lesion Formation in DNA by the Direct Effect of Ionizing Radiation

  摘要：

  Electron transfer via nucleobase hole migration has been extensively studied in recent years. Holes are produced in DNA via the direct effect of gamma-radiolysis. However, the contribution of this pathway to DNA damage is difficult to discern because common products are formed via the direct and indirect (e.g., hydroxyl radical) pathways. A molecular probe (1) was designed that serves as a repository for holes in DNA. Upon one-electron oxidation, 1 fragments to fdU, which is an alkali-labile lesion. Incorporation of 1 in synthetic DNA enables one to determine the contribution of hole transfer to DNA damage by gamma-radiolysis. We find that hole migration is the predominant pathway for alkali-labile lesion formation when DNA is exposed to Cs-137 in solution.

  DOI：

  10.1021/ja0678931