1-[2′-deoxy-3′,5′-bis{O-(p-toluoyl)}-β-D-ribofuranosyl]-4-(phenanthren-9-yl)-1H-1,2,3-triazole | 1416717-97-9

• 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-3′,5′-bis{O-(p-toluoyl)}-β-D-ribofuranosyl]-4-(phenanthren-9-yl)-1H-1,2,3-triazole
• 英文别名: [(2R,3S,5R)-3-(4-methylbenzoyl)oxy-5-(4-phenanthren-9-yltriazol-1-yl)oxolan-2-yl]methyl 4-methylbenzoate
• CAS: 1416717-97-9
• 化学式: C₃₇H₃₁N₃O₅
• 分子量: 597.67
• InChiKey: WKYAFKNPZMWEPI-BMPTZRATSA-N

物化性质

• 沸点：
  778.9±70.0 °C(Predicted)
• 密度：
  1.29±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  7.9
• 重原子数：
  45
• 可旋转键数：
  9
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  92.5
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  1-[2′-deoxy-3′,5′-bis{O-(p-toluoyl)}-β-D-ribofuranosyl]-4-(phenanthren-9-yl)-1H-1,2,3-triazole 在 四氮唑 、 4-二甲氨基吡啶 、 sodium methylate 、 N,N-二异丙基乙胺 作用下， 以 吡啶 、 甲醇 为溶剂， 反应 16.0h， 生成
  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 、 copper(II) sulfate 、 sodium ascorbate 、 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 、 乙醚 、 二氯甲烷 、 水 为溶剂， 反应 12.0h， 生成 1-[2′-deoxy-3′,5′-bis{O-(p-toluoyl)}-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

• 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.