2-(3,5-dimethylpyrazol-1-yl)adenosine | 56720-68-4

• 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: 2-(3,5-dimethylpyrazol-1-yl)adenosine
• CAS: 56720-68-4
• 化学式: C₁₅H₁₉N₇O₄
• 分子量: 361.36
• InChiKey: IZOYRMOSNLBWAM-IDTAVKCVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.18
• 重原子数：
  26.0
• 可旋转键数：
  3.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  157.36
• 氢给体数：
  4.0
• 氢受体数：
  11.0

反应信息

• 作为反应物：
  描述：

  2-(3,5-dimethylpyrazol-1-yl)adenosine 在 吡啶 、 sodium nitrite 作用下， 以 水 、 溶剂黄146 为溶剂， 反应 32.0h， 生成 5′-O-(4,4′-dimethoxytrityl)-2-(3,5-dimethylpyrazol-1-yl)inosine
  参考文献：
  名称：

  Metal-Ion-Mediated Base Pairing between Natural Nucleobases and Bidentate 3,5-Dimethylpyrazolyl-Substituted Purine Ligands

  摘要：

  The potential of three modified purine bases, namely, 6-(3,5-dimethylpyrazol-1-yl)purine, 2-(3,5-dimethylpyrazol-1-yl)hypoxanthine, and 2-(3,5-dimethylpyrazol-1-yl)adenine, for metal-ion-mediated base pairing within an oligonucleotide environment has been investigated. The respective modified nucleosides were incorporated in the middle of 9-mer 2'-O-methyl oligonucleotides and the hybridization of these modified oligonucleotides with their unmodified counterparts studied by UV and CD spectrometry in the absence and presence of Cu2+ or Zn2+. All of the modified oligonucleotides formed more stable duplexes in the presence of divalent metal ions than in the absence thereof, but with different preferences for the complementary oligonucleotide. The oligonucleotide incorporating 2-(3,5-dimethylpyrazol-1-yl)hypoxanthine readily accepted any of the natural nucleobases opposite to this modified base regardless of whether Cu2+ or Zn2+ was used as the bridging metal ion. The other two oligonucleotides, on the other hand, were much more discriminating, exhibiting markedly elevated Tm values only in the presence of Cu2+ and only when certain natural nucleobases were paired with the modified one. The origin of the selectivity (or promiscuity) of the metal-ion-mediated base pairing is discussed in terms of the ability of the modified nucleobases, as well as their natural counterparts, to serve as anionic ligands.

  DOI：

  10.1021/jo501237r
• 作为产物：
  描述：

  2,6-bis(3,5-dimethylpyrazol-1-yl)purineriboside 在 氨 作用下， 以 水 为溶剂， 反应 24.0h， 以31%的产率得到2-(3,5-dimethylpyrazol-1-yl)adenosine
  参考文献：
  名称：

  Metal-Ion-Mediated Base Pairing between Natural Nucleobases and Bidentate 3,5-Dimethylpyrazolyl-Substituted Purine Ligands

  摘要：

  The potential of three modified purine bases, namely, 6-(3,5-dimethylpyrazol-1-yl)purine, 2-(3,5-dimethylpyrazol-1-yl)hypoxanthine, and 2-(3,5-dimethylpyrazol-1-yl)adenine, for metal-ion-mediated base pairing within an oligonucleotide environment has been investigated. The respective modified nucleosides were incorporated in the middle of 9-mer 2'-O-methyl oligonucleotides and the hybridization of these modified oligonucleotides with their unmodified counterparts studied by UV and CD spectrometry in the absence and presence of Cu2+ or Zn2+. All of the modified oligonucleotides formed more stable duplexes in the presence of divalent metal ions than in the absence thereof, but with different preferences for the complementary oligonucleotide. The oligonucleotide incorporating 2-(3,5-dimethylpyrazol-1-yl)hypoxanthine readily accepted any of the natural nucleobases opposite to this modified base regardless of whether Cu2+ or Zn2+ was used as the bridging metal ion. The other two oligonucleotides, on the other hand, were much more discriminating, exhibiting markedly elevated Tm values only in the presence of Cu2+ and only when certain natural nucleobases were paired with the modified one. The origin of the selectivity (or promiscuity) of the metal-ion-mediated base pairing is discussed in terms of the ability of the modified nucleobases, as well as their natural counterparts, to serve as anionic ligands.

  DOI：

  10.1021/jo501237r