N-acetyl-2-methoxy-8-oxo-7,8-dihydroadenosine 2’,3’,5’-triacetate | 1423158-23-9

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 吡咯并嘧啶核苷和核苷酸
• 英文名称: N-acetyl-2-methoxy-8-oxo-7,8-dihydroadenosine 2’,3’,5’-triacetate
• CAS: 1423158-23-9
• 化学式: C₁₉H₂₃N₅O₁₀
• 分子量: 481.419
• InChiKey: IVYDZXLNZTXYDZ-LSCFUAHRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.59
• 重原子数：
  34.0
• 可旋转键数：
  7.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  190.03
• 氢给体数：
  2.0
• 氢受体数：
  13.0

反应信息

• 作为产物：
  描述：

  、 乙酸酐 以 二氯甲烷 为溶剂， 生成 N-acetyl-2-methoxy-8-oxo-7,8-dihydroadenosine 2’,3’,5’-triacetate 、 N-acetyl-8-oxo-7,8-dihydroadenosine-,2’,3’,5’-triacetate
  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