d(A)4 | 68726-43-2

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 核苷和核苷酸类似物
• 英文名称: d(A)4
• 英文别名: dAdo-P-dAdo-P-dAdo-P-dAdo；[(2R,3S,5R)-5-(6-aminopurin-9-yl)-2-[[[(2R,3S,5R)-5-(6-aminopurin-9-yl)-2-[[[(2R,3S,5R)-5-(6-aminopurin-9-yl)-2-(hydroxymethyl)oxolan-3-yl]oxy-hydroxyphosphoryl]oxymethyl]oxolan-3-yl]oxy-hydroxyphosphoryl]oxymethyl]oxolan-3-yl] [(2R,3S,5R)-5-(6-aminopurin-9-yl)-3-hydroxyoxolan-2-yl]methyl hydrogen phosphate
• CAS: 68726-43-2
• 化学式: C₄₀H₄₉N₂₀O₁₈P₃
• 分子量: 1190.87
• InChiKey: LHOLFVJQXOBQET-OHULCMFMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -6.2
• 重原子数：
  81
• 可旋转键数：
  20
• 环数：
  12.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  523
• 氢给体数：
  9
• 氢受体数：
  34

反应信息

• 作为产物：
  描述：

  在 ammonium hydroxide 、 N₁,N₁,N₃,N₃-tetrametylquanidium salt of 2-pyridinecarboxaldehyde oxim 作用下， 生成 d(A)4
  参考文献：
  名称：

  SELECTIVE REMOVAL OF TERMINAL DIMETHOXYTRITYL GROUPS

  摘要：

  N6'N6,3',5'-O-保护的脱氧腺苷衍生物被发现是合成寡脱氧核糖核苷酸的关键中间体。用3%三氯乙酸的硝基甲烷-甲醇(95:5)溶液处理受保护的脱氧腺苷衍生物，得到相应的脱二甲氧基三苯甲基化的脱氧腺苷衍生物，且不会对糖苷键造成任何损害。

  DOI：

  10.1246/cl.1983.1661

文献信息

• Formation of Modified Cytosine Residues in the Presence of Depurinated DNA
  作者：Claus Rentel、Xiaojing Wang、Michael Batt、Christine Kurata、Jay Oliver、Hans Gaus、Achim H. Krotz、James V. McArdle、Daniel C. Capaldi

  DOI：10.1021/jo050767f

  日期：2005.9.1

  Depurination is an important degradation pathway for antisense phosphorothioate oligonucleotides under conditions of thermal stress. We present evidence showing that depurinated oligonucleotides react with cytosine-containing sequences giving products containing a 6-(2-deoxy-beta-D-erythropentofuranosyl)-3-(2-oxopropyl)imidazo[1,2-c]pyrimidin-5(6H)-one residue. Further, we demonstrate that the same product is formed upon treatment of 2'-deoxycytidine with 4-oxo-2-pentenal, the latter being an expected byproduct of serial elimination reactions at apurinic sites. In addition to being important for synthetic oligonucleotides, apurinic site formation in cellular DNA is a common occurrence. Because repair of these sites can result in the production of 4-oxo-2-pentenal, it is interesting to speculate whether 6-(2-deoxy-beta-D-erythro-pentofuranosyl)-3-(2-oxopropyl)imidazo[1,2-c]pyrimidin-5(6H)-one residues can form in vivo.