C8-(4-carboxyphenyl)-2'-deoxyguanosine

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 嘌呤核苷
• 英文名称: C8-(4-carboxyphenyl)-2'-deoxyguanosine
• 英文别名: 4-[2-amino-9-[(2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-6-oxo-1H-purin-8-yl]benzoic acid
• 化学式: C₁₇H₁₇N₅O₆
• 分子量: 387.352
• InChiKey: ATPDGDBHCPLRHC-HBNTYKKESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.6
• 重原子数：
  28
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  172
• 氢给体数：
  5
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  N,N-二甲基甲酰胺二甲基缩醛 、 C8-(4-carboxyphenyl)-2'-deoxyguanosine 以 甲醇 为溶剂， 反应 48.0h， 以96%的产率得到N2-(N,N-dimethylformamidine)-C8-(4-carboxyphenyl)-2'-deoxyguanosine
  参考文献：
  名称：

  A General Synthesis of C8-Arylpurine Phosphoramidites

  摘要：

  我们开发了一种合成 C8 芳基嘌呤磷酰胺的通用方案。C8-溴-2′-脱氧鸟苷的 C8-芳基化是关键步骤，是通过使用铃木偶联法实现的。由于偶联反应是在水性条件下进行的，因此不需要先保护羟基，然后再去保护羟基，从而节省了多个步骤，提高了总产率。一旦引入 C8 芳基，糖苷键就会对酸催化裂解变得非常敏感。用相应的 N,N-二甲基甲酰胺衍生物保护氨基基团可提高衍生物的稳定性。合成的 C8 芳基嘌呤被成功用于制备合成寡核苷酸。

  DOI：

  10.3390/molecules14093339
• 作为产物：
  描述：

  2'-脱氧鸟苷 、 (p-carboxymethyl)benzenediazonium hydrogen sulfate 在 sodium hydroxide 作用下， 反应 24.0h， 生成 C8-(4-carboxyphenyl)-2'-deoxyguanosine
  参考文献：
  名称：

  Different Patterns of Mutagenicity of Arenediazonium Ions in V79 Cells and Salmonella typhimurium TA102: Evidence for Different Mechanisms of Action

  摘要：

  The edible mushroom Agaricus bisporus contains several arylhydrazines and arenediazonium ions that are genotoxins. The mechanism whereby arylhydrazines and arenediazonium ions are genotoxic is unknown and may be due to the arenediazonium ion itself or to aryl radicals. The reactions of four arenediazonium ions (p-X-C6H5N2+, X = -CH3, -CH2OH, -CH2OCH3, -CO2H) with purine bases, their mutagenicity, their ability to cause DNA damage, and their tendency toward free radical formation have been studied to elucidate the genotoxic species. It is suggested that either the arenediazonium or aryl radical can act as the ultimate genotoxin. Which species is dominant is dependent upon the arenediazonium ion reduction potential. This relationship may be useful in designing future studies of arenediazonium ion genotoxicity.

  DOI：

  10.1021/jf00058a014

文献信息

• Different Patterns of Mutagenicity of Arenediazonium Ions in V79 Cells and Salmonella typhimurium TA102: Evidence for Different Mechanisms of Action
  作者：Terence Lawson、Peter M. Gannett、Wai-Ming Yau、Nar S. Dalal、Bela Toth

  DOI：10.1021/jf00058a014

  日期：1995.10

  The edible mushroom Agaricus bisporus contains several arylhydrazines and arenediazonium ions that are genotoxins. The mechanism whereby arylhydrazines and arenediazonium ions are genotoxic is unknown and may be due to the arenediazonium ion itself or to aryl radicals. The reactions of four arenediazonium ions (p-X-C6H5N2+, X = -CH3, -CH2OH, -CH2OCH3, -CO2H) with purine bases, their mutagenicity, their ability to cause DNA damage, and their tendency toward free radical formation have been studied to elucidate the genotoxic species. It is suggested that either the arenediazonium or aryl radical can act as the ultimate genotoxin. Which species is dominant is dependent upon the arenediazonium ion reduction potential. This relationship may be useful in designing future studies of arenediazonium ion genotoxicity.
• A General Synthesis of C8-Arylpurine Phosphoramidites
  作者：Vorasit Vongsutilers、Jonathan Daft、Kevin Shaughnessy、Peter Gannett

  DOI：10.3390/molecules14093339

  日期：——

  A general scheme for the synthesis of C8-arylpurine phosphoramidites has been developed. C8-Arylation of C8-bromo-2′-deoxyguanosine is the key step and has been achieved through the use of a Suzuki coupling. Since the coupling reaction is conducted under aqueous conditions, it is unnecessary to protect and then deprotect the hydroxyl groups, thus saving several steps and improving overall yields. Once the C8-arylgroup is introduced, the glycosidic bond becomes very sensitive to acid catalyzed cleavage. Protection of the amino groups as the corresponding N,N-dimethylformamidine derivative improves stability of the derivatives. Synthetic C8-arylpurines were successfully used to prepare synthetic oligonucleotides.

  我们开发了一种合成 C8 芳基嘌呤磷酰胺的通用方案。C8-溴-2′-脱氧鸟苷的 C8-芳基化是关键步骤，是通过使用铃木偶联法实现的。由于偶联反应是在水性条件下进行的，因此不需要先保护羟基，然后再去保护羟基，从而节省了多个步骤，提高了总产率。一旦引入 C8 芳基，糖苷键就会对酸催化裂解变得非常敏感。用相应的 N,N-二甲基甲酰胺衍生物保护氨基基团可提高衍生物的稳定性。合成的 C8 芳基嘌呤被成功用于制备合成寡核苷酸。