8-bromo-1-methylguanosine

• 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: 8-bromo-1-methylguanosine
• 英文别名: 2-amino-8-bromo-9-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-1-methylpurin-6-one
• 化学式: C₁₁H₁₄BrN₅O₅
• 分子量: 376.167
• InChiKey: AWYUGIKSVQBHOM-UUOKFMHZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.5
• 重原子数：
  22
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  146
• 氢给体数：
  4
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  8-bromo-1-methylguanosine 以 水 、 叔丁醇 为溶剂， 以100%的产率得到1-甲基鸟酐
  参考文献：
  名称：

  一电子氧化鸟苷的互变异构体。

  摘要：

  DOI：

  10.1002/anie.200501087

文献信息

• New Insights into the Reaction Paths of Hydroxyl Radicals with 2′-Deoxyguanosine
  作者：Chryssostomos Chatgilialoglu、Mila D’Angelantonio、Gabriel Kciuk、Krzysztof Bobrowski

  DOI：10.1021/tx2003245

  日期：2011.12.19

  The reaction of HO(center dot) radical with 2'-deoxyguanosine is intensively studied as a model for DNA damage. Several aspects related to the reaction paths responsible for the most relevant lesions are not well understood. We have reinvestigated the reaction of HO(center dot) with 2'-deoxyguanosine by pulse radiolysis and extended our studies to a variety of substituted derivatives. The main path of hydrogen abstraction was confirmed to be from the exocyclic NH(2) group, followed by a water-assisted tautomerization. The rate constant (k = 2.3 x 10(4) s(-1)) obtained from the spectral changes at 620 rim is influenced by the substituent at the C8 position. When N1-H is replaced by N1-CH(3), the tautomerization does not occur. The spectral changes at 370 nm that correspond to a rate constant of 6.9 x 10(5) s(-1) were assigned to the cyclization of 2'-deoxyguanosin-5'-yl radical with formation of 5',8-cyclo-2'-deoxyguanosine as the product. When NEt(2) replaces the exocyclic NH(2), the spectral changes at all wavelengths follow second-order kinetics, suggesting a "slow" ring-opening of the 8-hydroxyl adduct of 2'-deoxyguanosine.
• Tautomers of One-Electron-Oxidized Guanosine
  作者：Chryssostomos Chatgilialoglu、Clara Caminal、Maurizio Guerra、Quinto G. Mulazzani

  DOI：10.1002/anie.200501087

  日期：2005.9.19