| 1435938-68-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• CAS: 1435938-68-3
• 化学式: C₂₁H₂₄N₃O₆P
• 分子量: 445.412
• InChiKey: PYDSDNKYIPZNKF-JXFKEZNVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.78
• 重原子数：
  31.0
• 可旋转键数：
  11.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  141.77
• 氢给体数：
  3.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  在 Ammonium hydroxide 作用下， 生成
  参考文献：
  名称：

  p-Stilbazole Moieties As Artificial Base Pairs for Photo-Cross-Linking of DNA Duplex

  摘要：

  In this study, we report a photo-cross-linking reaction between p-stilbazole moieties p-Stilbazoles were introduced into base paring positions of complementary DNA strands. The [2 + 2] photocycloaddition reaction occurred rapidly upon light irradiation at 340 nm. Consequently, duplex was cross-linked and highly stabilized after 3 min irradiation. The CD spectrum of the cross-linked duplex indicated that the B-form double-helical structure was not severely distorted. NMR analysis revealed only one conformation of the duplex prior to UV irradiation, whereas two diastereomers were detected after the photo-cross-linking reaction. Before UV irradiation, p-stilbazole can adopt two different stacking modes because of rotation around the single bond between the phenyl and vinyl groups; these conformations cannot be discriminated on the NMR time scale due to rapid interconversion. However, photo-cross-linking fixed the conformation and enabled discrimination both by NMR and HPLC. The artificial base pair of p-methylstilbazolium showed almost the same reactivity as p-stilbazole, indicating that positive charge does not affect the reactivity. When a natural nucleobase was present in the complementary strand opposite p-stilbazole, the duplex was significantly destabilized relative to the duplex with paired p-stilbazole moieties and no photoreaction occurred between p-stilbazole and the nucleobase. The p-stilbazole pair has potential as a "third base pair" for nanomaterials due to its high stability and superb orthogonality.

  DOI：

  10.1021/ja401835j
• 作为产物：
  描述：

  在 吡啶 、 水 、 碘 、 三氟乙酸 作用下， 以 四氢呋喃 、 乙腈 为溶剂， 反应 4.08h， 生成
  参考文献：
  名称：

  p-Stilbazole Moieties As Artificial Base Pairs for Photo-Cross-Linking of DNA Duplex

  摘要：

  In this study, we report a photo-cross-linking reaction between p-stilbazole moieties p-Stilbazoles were introduced into base paring positions of complementary DNA strands. The [2 + 2] photocycloaddition reaction occurred rapidly upon light irradiation at 340 nm. Consequently, duplex was cross-linked and highly stabilized after 3 min irradiation. The CD spectrum of the cross-linked duplex indicated that the B-form double-helical structure was not severely distorted. NMR analysis revealed only one conformation of the duplex prior to UV irradiation, whereas two diastereomers were detected after the photo-cross-linking reaction. Before UV irradiation, p-stilbazole can adopt two different stacking modes because of rotation around the single bond between the phenyl and vinyl groups; these conformations cannot be discriminated on the NMR time scale due to rapid interconversion. However, photo-cross-linking fixed the conformation and enabled discrimination both by NMR and HPLC. The artificial base pair of p-methylstilbazolium showed almost the same reactivity as p-stilbazole, indicating that positive charge does not affect the reactivity. When a natural nucleobase was present in the complementary strand opposite p-stilbazole, the duplex was significantly destabilized relative to the duplex with paired p-stilbazole moieties and no photoreaction occurred between p-stilbazole and the nucleobase. The p-stilbazole pair has potential as a "third base pair" for nanomaterials due to its high stability and superb orthogonality.

  DOI：

  10.1021/ja401835j