1-(2′-deoxy-β-D-ribofuranosyl)-4-(phenanthren-9-yl)-1H-1,2,3-triazole | 1416718-01-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 菲及其衍生物
• 英文名称: 1-(2′-deoxy-β-D-ribofuranosyl)-4-(phenanthren-9-yl)-1H-1,2,3-triazole
• 英文别名: (2R,3S,5R)-2-(hydroxymethyl)-5-(4-phenanthren-9-yltriazol-1-yl)oxolan-3-ol
• CAS: 1416718-01-8
• 化学式: C₂₁H₁₉N₃O₃
• 分子量: 361.4
• InChiKey: UMHZOKZJSDUHIU-PWRODBHTSA-N

物化性质

• 沸点：
  657.0±65.0 °C(Predicted)
• 密度：
  1.45±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  27
• 可旋转键数：
  3
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  80.4
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  1-(2′-deoxy-β-D-ribofuranosyl)-4-(phenanthren-9-yl)-1H-1,2,3-triazole 、 4,4'-双甲氧基三苯甲基氯 在 4-二甲氨基吡啶 作用下， 以 吡啶 为溶剂， 反应 16.0h， 以70%的产率得到1-(5′-O-(4,4′-dimethoxytrityl)-2-deoxy-β-D-ribofuranosyl)-4-(phenanthren-9-yl)-1H-1,2,3-triazole
  参考文献：
  名称：

  Triazolyl Donor/Acceptor Chromophore Decorated Unnatural Nucleosides and Oligonucleotides with Duplex Stability Comparable to That of a Natural Adenine/Thymine Pair

  摘要：

  We report the design and synthesis of triazolyl donor/acceptor unnatural nucleosides via click chemistry and studies on the duplex stabilization of DNA containing two such new nucleosides. The observed duplex stabilization among the self-pair/heteropair has been found to be comparable to that of a natural A/T pair. Our observations on the comparable duplex stabilization has been explained on the basis of possible pi-pi stacking and/or charge transfer interactions between the pairing partners. The evidence of ground-state charge transfer complexation came from the UV-vis spectra and the static quenching of fluorescence in a heteropair. We have also exploited one of our unnatural DNAs in stabilizing abasic DNA.

  DOI：

  10.1021/jo302033f
• 作为产物：
  描述：

  2-deoxy-D-ribose 在 吡啶 、 盐酸 、 4-二甲氨基吡啶 、 叠氮基三甲基硅烷 、 三氟化硼乙醚 、 sodium methylate 、 copper(II) sulfate 、 sodium ascorbate 、 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 、 甲醇 、 乙醚 、 二氯甲烷 、 水 为溶剂， 反应 12.0h， 生成 1-(2′-deoxy-β-D-ribofuranosyl)-4-(phenanthren-9-yl)-1H-1,2,3-triazole
  参考文献：
  名称：

  Triazolyl Donor/Acceptor Chromophore Decorated Unnatural Nucleosides and Oligonucleotides with Duplex Stability Comparable to That of a Natural Adenine/Thymine Pair

  摘要：

  We report the design and synthesis of triazolyl donor/acceptor unnatural nucleosides via click chemistry and studies on the duplex stabilization of DNA containing two such new nucleosides. The observed duplex stabilization among the self-pair/heteropair has been found to be comparable to that of a natural A/T pair. Our observations on the comparable duplex stabilization has been explained on the basis of possible pi-pi stacking and/or charge transfer interactions between the pairing partners. The evidence of ground-state charge transfer complexation came from the UV-vis spectra and the static quenching of fluorescence in a heteropair. We have also exploited one of our unnatural DNAs in stabilizing abasic DNA.

  DOI：

  10.1021/jo302033f

文献信息

• Unnatural triazolyl nucleoside stabilizes an abasic site containing DNA duplex equally as the stabilization of a natural A–T pair
  作者：Subhendu Sekhar Bag、Rajen Kundu、Sangita Talukdar

  DOI：10.1039/c3ra44120b

  日期：——

  A better than reported abasic duplex stabilization was achieved with the novel triazolylphenanthrene nucleoside TPhenBDo. The large surface area, polarizability and strong stacking propensity of triazolylphenanthrene play a major role in the thermal stabilization of the TPhenBDo–Φ duplex comparable to that of a natural A–T pair via a strong intercalative stacking interaction.

  使用新型三唑基苯并蒽核苷TPhenBDo，获得了比报道更好的无碱二聚体稳定性。三唑基苯并蒽具有较大的表面积、极化性和强叠加倾向，这些因素在TPhenBDo–Φ二聚体的热稳定性中起着主要作用，其稳定性可与自然的A–T对相媲美，得益于强的插层叠加相互作用。
• Triazolyl Donor/Acceptor Chromophore Decorated Unnatural Nucleosides and Oligonucleotides with Duplex Stability Comparable to That of a Natural Adenine/Thymine Pair
  作者：Subhendu Sekhar Bag、Sangita Talukdar、Katsuhiko Matsumoto、Rajen Kundu

  DOI：10.1021/jo302033f

  日期：2013.1.18

  We report the design and synthesis of triazolyl donor/acceptor unnatural nucleosides via click chemistry and studies on the duplex stabilization of DNA containing two such new nucleosides. The observed duplex stabilization among the self-pair/heteropair has been found to be comparable to that of a natural A/T pair. Our observations on the comparable duplex stabilization has been explained on the basis of possible pi-pi stacking and/or charge transfer interactions between the pairing partners. The evidence of ground-state charge transfer complexation came from the UV-vis spectra and the static quenching of fluorescence in a heteropair. We have also exploited one of our unnatural DNAs in stabilizing abasic DNA.