N2-isobutyryl-8-(2-pyridyl)-2'-deoxyguanosine | 1259202-42-0

• 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: N2-isobutyryl-8-(2-pyridyl)-2'-deoxyguanosine
• CAS: 1259202-42-0
• 化学式: C₁₉H₂₂N₆O₅
• 分子量: 414.421
• InChiKey: NMIBWOOPTRQSCK-YNEHKIRRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.42
• 重原子数：
  30.0
• 可旋转键数：
  5.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  155.25
• 氢给体数：
  4.0
• 氢受体数：
  9.0

反应信息

• 作为反应物：
  描述：

  N2-isobutyryl-8-(2-pyridyl)-2'-deoxyguanosine 、 4,4'-双甲氧基三苯甲基氯 在 吡啶 作用下， 反应 0.67h， 以96%的产率得到O5'-(4,4'-dimethoxytrityl)-N2-isobutyryl-8-(2-pyridyl)-2'-deoxyguanosine
  参考文献：
  名称：

  Cation-Mediated Energy Transfer in G-Quadruplexes Revealed by an Internal Fluorescent Probe

  摘要：

  A single pyridine unit incorporated into G-quadruplex DNA has revealed efficient energy transfer reactions in cation-containing G-quadruplexes. 8-(2-Pyridyl)-2'-deoxyguanosine, "2PyG", is a highly sensitive internal fluorescent probe of G-quadruplex folding and energy transfer. 2PyG was minimally disruptive to G-quadruplex folding and exhibited intense fluorescence, even when it was base-stacked with other guanine residues. Using 2PyG we have quantified energy transfer efficiencies within G-quadruplex structures prepared under conditions of excess Na+/K+ (110 mM) or in 40% polyethylene glycol (PEG) under salt deficient conditions. G-quadruplex structures containing coordinated cations exhibited efficient DNA-to-probe energy transfer reactions (eta(t) = 0.11-0.41), while PEG-folded G-quadruplexes exhibited very little energy transfer (eta(t) = 0.02-0.07). Experiments conducted using unmodified G-quadruplexes suggest that cation coordination at the O-6 position of guanine residues results in enhanced quantum yields of G-quadruplex nucleobases that, in turn, serve as efficient energy donors to 2PyG. Given the growing interest in G-quadruplex-based devices and materials, these results will provide important design principles toward harnessing the potentially useful photophysical properties of G-quadruplex wires and other G-rich structures.

  DOI：

  10.1021/ja1079578
• 作为产物：
  描述：

  3',5'-O-bis(tert-butyldimethylsilyl)-N2-isobutyryl-8-(2-pyridyl)-O6-(2-trimethylsilylethyl)-2'-deoxyguanosine 在 四丁基氟化铵 作用下， 以 四氢呋喃 为溶剂， 反应 17.0h， 以91%的产率得到N2-isobutyryl-8-(2-pyridyl)-2'-deoxyguanosine
  参考文献：
  名称：

  Cation-Mediated Energy Transfer in G-Quadruplexes Revealed by an Internal Fluorescent Probe

  摘要：

  A single pyridine unit incorporated into G-quadruplex DNA has revealed efficient energy transfer reactions in cation-containing G-quadruplexes. 8-(2-Pyridyl)-2'-deoxyguanosine, "2PyG", is a highly sensitive internal fluorescent probe of G-quadruplex folding and energy transfer. 2PyG was minimally disruptive to G-quadruplex folding and exhibited intense fluorescence, even when it was base-stacked with other guanine residues. Using 2PyG we have quantified energy transfer efficiencies within G-quadruplex structures prepared under conditions of excess Na+/K+ (110 mM) or in 40% polyethylene glycol (PEG) under salt deficient conditions. G-quadruplex structures containing coordinated cations exhibited efficient DNA-to-probe energy transfer reactions (eta(t) = 0.11-0.41), while PEG-folded G-quadruplexes exhibited very little energy transfer (eta(t) = 0.02-0.07). Experiments conducted using unmodified G-quadruplexes suggest that cation coordination at the O-6 position of guanine residues results in enhanced quantum yields of G-quadruplex nucleobases that, in turn, serve as efficient energy donors to 2PyG. Given the growing interest in G-quadruplex-based devices and materials, these results will provide important design principles toward harnessing the potentially useful photophysical properties of G-quadruplex wires and other G-rich structures.

  DOI：

  10.1021/ja1079578