| 1314078-29-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 三苯基化合物
• CAS: 1314078-29-9
• 化学式: C₆₂H₅₉Br₂N₄O₁₁P
• 分子量: 1226.95
• InChiKey: CMBXANPYXSZZGN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  12.81
• 重原子数：
  80.0
• 可旋转键数：
  25.0
• 环数：
  10.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  166.4
• 氢给体数：
  0.0
• 氢受体数：
  13.0

反应信息

• 作为产物：
  描述：

  3,4,9,10-苝四羧酸二酐 在 吡啶 、 4-二甲氨基吡啶 、 硫酸 、 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 反应 3.5h， 生成
  参考文献：
  名称：

  Synthesis of a Dibromoperylene Phosphoramidite Building Block and Its Incorporation at the 5′ End of a G-Quadruplex Forming Oligonucleotide: Spectroscopic Properties and Structural Studies of the Resulting Dibromoperylene Conjugate

  摘要：

  Previous studies indicate that some perylene bisimide derivatives can drive the assembly of DNA G-quadruplexes, thus suggesting the possible advantage in the adoption of perylene-conjugated G-rich oligonucleotides in biological and biotechnological applications. Nevertheless, the typical poor solubility of perylene bisimides strongly limits the number of suitable chemical strategies to prepare perylene-conjugated oligonucleotides. In order to overcome these difficulties, we employed the earlier described core twisted perylene derivatives possessing unique optical and electronic properties, besides good solubility in common solvents. As a first result, the large-scale synthesis of a new dibromoperylene derivative (PEOEBr) phosphoramidite building block is herein reported. Furthermore, the structural behavior of the conjugated PEOEBr-GGGTTAGGG (HTRp2) human telomeric repeat was investigated by using CD, UV, fluorescence, and gel electrophoresis techniques in desalted water and in K+- and Na+-containing buffers. We observed that the peculiar property of PEOEBr moieties to form dimers instead of extended aggregates drives the HTRp2 strands toward dimerization and mainly promotes the formation of quadruplex species having both the 5'-ends located at the same side of the structures. However, the counterions present in solutions (K+ or Na+) as well as the strand concentration, also contribute to influence the topology and the stoichiometry of formed structures. Furthermore, unlike the unmodified sequence GGGTTAGGG (HTR2), HTRp2 strands quickly associate into G-quadruplexes even in desalted water, as assessed by CD experiments.

  DOI：

  10.1021/bc100526q