8-oxo-7,8-dihydroinosine tribenzoate | 1423158-41-1

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物
• 英文名称: 8-oxo-7,8-dihydroinosine tribenzoate
• CAS: 1423158-41-1
• 化学式: C₃₁H₂₄N₄O₉
• 分子量: 596.553
• InChiKey: HQJNSWLBNVEQAT-VBHAUSMQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.62
• 重原子数：
  44.0
• 可旋转键数：
  8.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.16
• 拓扑面积：
  171.67
• 氢给体数：
  2.0
• 氢受体数：
  11.0

反应信息

• 作为反应物：
  描述：

  8-oxo-7,8-dihydroinosine tribenzoate 在 氯化亚砜 作用下， 反应 48.0h， 以55%的产率得到6-chloro-8-oxo-7,8-dihydropururinoriboside tribenzoate
  参考文献：
  名称：

  Oxidation of Adenosine and Inosine: The Chemistry of 8-Oxo-7,8-dihydropurines, Purine Iminoquinones, and Purine Quinones as Observed by Ultrafast Spectroscopy

  摘要：

  Oxidative damage to purine nucleic acid bases proceeds through quinoidal intermediates derived from their corresponding 8-oxo-7,8-dihydropurine bases. Oxidation studies of 8-oxo-7,8-dihyroadenosine and 8-oxo-7,8-dihydroinosine indicate that these quinoidal species can produce stable cross links with a wide variety of nucleophiles in the 2-positions of the purines. An azide precursor for the adenosine iminoquinone has been synthesized and applied in ultrafast transient absorption spectroscopic studies. Thus, the adenosine iminoquinone can be observed directly, and its susceptibility to nudeophilic attack with various nucleophiles as well as the stability of the resulting cross linked species have been evaluated Finally, these observations indicate that this azide might be a very useful photoaffurity labeling agent, because the reactive intermediate, adenosine iminoquinone, is such a good mimic for the universal purine base adenosine.

  DOI：

  10.1021/ja3068148
• 作为产物：
  描述：

  8-氧腺苷 在 吡啶 、 溶剂黄146 、 sodium nitrite 作用下， 以 水 为溶剂， 生成 8-oxo-7,8-dihydroinosine tribenzoate
  参考文献：
  名称：

  Oxidation of Adenosine and Inosine: The Chemistry of 8-Oxo-7,8-dihydropurines, Purine Iminoquinones, and Purine Quinones as Observed by Ultrafast Spectroscopy

  摘要：

  Oxidative damage to purine nucleic acid bases proceeds through quinoidal intermediates derived from their corresponding 8-oxo-7,8-dihydropurine bases. Oxidation studies of 8-oxo-7,8-dihyroadenosine and 8-oxo-7,8-dihydroinosine indicate that these quinoidal species can produce stable cross links with a wide variety of nucleophiles in the 2-positions of the purines. An azide precursor for the adenosine iminoquinone has been synthesized and applied in ultrafast transient absorption spectroscopic studies. Thus, the adenosine iminoquinone can be observed directly, and its susceptibility to nudeophilic attack with various nucleophiles as well as the stability of the resulting cross linked species have been evaluated Finally, these observations indicate that this azide might be a very useful photoaffurity labeling agent, because the reactive intermediate, adenosine iminoquinone, is such a good mimic for the universal purine base adenosine.

  DOI：

  10.1021/ja3068148