1-(5′-O-(4,4′-dimethoxytrityl)-2-deoxy-β-D-ribofuranosyl)-4-(4-nitrophenyl)-1H-1,2,3-triazole | 1416718-06-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 三苯基化合物
• 英文名称: 1-(5′-O-(4,4′-dimethoxytrityl)-2-deoxy-β-D-ribofuranosyl)-4-(4-nitrophenyl)-1H-1,2,3-triazole
• 英文别名: (2R,3S,5R)-2-[[bis(4-methoxyphenyl)-phenylmethoxy]methyl]-5-[4-(4-nitrophenyl)triazol-1-yl]oxolan-3-ol
• CAS: 1416718-06-3
• 化学式: C₃₄H₃₂N₄O₇
• 分子量: 608.651
• InChiKey: UGYGQHVWTJLSSR-WIHCDAFUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 重原子数：
  45
• 可旋转键数：
  10
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  134
• 氢给体数：
  1
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  1-(5′-O-(4,4′-dimethoxytrityl)-2-deoxy-β-D-ribofuranosyl)-4-(4-nitrophenyl)-1H-1,2,3-triazole 、 双(二异丙基氨基)(2-氰基乙氧基)膦 在 四氮唑 、 N,N-二异丙基乙胺 作用下， 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 、 sodium methylate 、 copper(II) sulfate 、 sodium ascorbate 、 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 、 吡啶 、 甲醇 、 乙醚 、 二氯甲烷 、 水 为溶剂， 反应 28.0h， 生成 1-(5′-O-(4,4′-dimethoxytrityl)-2-deoxy-β-D-ribofuranosyl)-4-(4-nitrophenyl)-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.