1-(2-deoxy-β-D-erythro-pentofuranosyl)-1,5-dihydro-6H-pyrazolo[3,4-d]pyrimidin-6-one | 329321-53-1

• 分子结构分类: 有机化合物 - 有机杂环化合物
• 英文名称: 1-(2-deoxy-β-D-erythro-pentofuranosyl)-1,5-dihydro-6H-pyrazolo[3,4-d]pyrimidin-6-one
• 英文别名: 8-aza-7-deaza-2'-deoxyisoinosine；1-[(2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-7H-pyrazolo[3,4-d]pyrimidin-6-one
• CAS: 329321-53-1
• 化学式: C₁₀H₁₂N₄O₄
• 分子量: 252.23
• InChiKey: JCPOBXGRNBQHHD-XLPZGREQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.3
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  109
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  1-(2-deoxy-β-D-erythro-pentofuranosyl)-1,5-dihydro-6H-pyrazolo[3,4-d]pyrimidin-6-one 在 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 、 吡啶 为溶剂， 反应 5.0h， 生成 6-(N,N-diphenylcarbamoyl)oxy-1-[2-deoxy-5-O-(4,4'-dimethoxytrityl)-β-D-erythro-pentofuranosyl]-1H-pyrazolo[3,4-d]pyrimidine 3'-[(2-cyanoethyl)-N,N-diisopropylphosphoramidite]
  参考文献：
  名称：

  Fluorescence Properties and Base Pair Stability of Oligonucleotides Containing 8-Aza-7-deaza-2′-deoxyisoinosine or 2′-Deoxyisoinosine

  摘要：

  The fluorescence and the base pairing properties of 8-aza-7-deaza-2'-deoxyisoinosine (1) are described and compared with those of 2'-deoxyisoinosine (2). The corresponding phosphoramidites (11, 12) are synthesized using the diphenyl-carbamoyl (DPC) residue for the 2-oxo group protection. The nucleosides 1 and 2 base pair with 2'-deoxy-5-methylisocytidine in DNA duplexes with antiparallel chain orientation and with 2'-deoxycytidine in a parallel DNA. These base pairs are less stable than the canonical dA-dT pair and that of 2'-deoxyinosine (4) with 2'-deoxycytidine. The fluorescence of the nucleosides 1 and 2 is quenched (similar to 95%) in duplex DNA. The residual fluorescence is used to determine the T-m-values, which are found to be the same as determined UV-spectrophotometrically.

  DOI：

  10.1080/15257770008045448
• 作为产物：
  描述：

  6-amino-1-(2-deoxy-β-D-erythro-pentofuranosyl)-1H-pyrazolo[3,4-d]pyrimidine 在 溶剂黄146 、 sodium nitrite 作用下， 以 水 为溶剂， 以69%的产率得到1-(2-deoxy-β-D-erythro-pentofuranosyl)-1,5-dihydro-6H-pyrazolo[3,4-d]pyrimidin-6-one
  参考文献：
  名称：

  Fluorescence Properties and Base Pair Stability of Oligonucleotides Containing 8-Aza-7-deaza-2′-deoxyisoinosine or 2′-Deoxyisoinosine

  摘要：

  The fluorescence and the base pairing properties of 8-aza-7-deaza-2'-deoxyisoinosine (1) are described and compared with those of 2'-deoxyisoinosine (2). The corresponding phosphoramidites (11, 12) are synthesized using the diphenyl-carbamoyl (DPC) residue for the 2-oxo group protection. The nucleosides 1 and 2 base pair with 2'-deoxy-5-methylisocytidine in DNA duplexes with antiparallel chain orientation and with 2'-deoxycytidine in a parallel DNA. These base pairs are less stable than the canonical dA-dT pair and that of 2'-deoxyinosine (4) with 2'-deoxycytidine. The fluorescence of the nucleosides 1 and 2 is quenched (similar to 95%) in duplex DNA. The residual fluorescence is used to determine the T-m-values, which are found to be the same as determined UV-spectrophotometrically.

  DOI：

  10.1080/15257770008045448