8-(2-Hydroxy-2-propyl)guanosin | 23844-15-7

• 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-(2-Hydroxy-2-propyl)guanosin
• 英文别名: 8-(1-hydroxy-1-methylethyl)guanosine；8-(2-hydroxypropan-2-yl)guanosine；2-amino-9-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-8-(2-hydroxypropan-2-yl)-1H-purin-6-one
• CAS: 23844-15-7
• 化学式: C₁₃H₁₉N₅O₆
• 分子量: 341.324
• InChiKey: DAMXRVHVWNCLQK-KQYNXXCUSA-N

物化性质

• 密度：
  1.95±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -3
• 重原子数：
  24
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  175
• 氢给体数：
  6
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  8-(2-Hydroxy-2-propyl)guanosin 在 水 、 一氧化二氮 作用下， 生成
  参考文献：
  名称：

  New Insights into the Reaction Paths of Hydroxyl Radicals with 2′-Deoxyguanosine

  摘要：

  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.

  DOI：

  10.1021/tx2003245