1-[2-deoxy-5-O-(4,4'-dimethoxytrityl)-β-D-ribofuranos-1-yl]-4,5-diiodoimidazole | 909869-58-5

• 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-[2-deoxy-5-O-(4,4'-dimethoxytrityl)-β-D-ribofuranos-1-yl]-4,5-diiodoimidazole
• 英文别名: (2R,3S,5R)-2-[[bis(4-methoxyphenyl)-phenylmethoxy]methyl]-5-(4,5-diiodoimidazol-1-yl)oxolan-3-ol
• CAS: 909869-58-5
• 化学式: C₂₉H₂₈I₂N₂O₅
• 分子量: 738.361
• InChiKey: HTJXEARGAYHLHE-JIMJEQGWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.3
• 重原子数：
  38
• 可旋转键数：
  9
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.28
• 拓扑面积：
  75
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  1-[2-deoxy-5-O-(4,4'-dimethoxytrityl)-β-D-ribofuranos-1-yl]-4,5-diiodoimidazole 在 乙基溴化镁 作用下， 以 四氢呋喃 为溶剂， 以56%的产率得到1-[2-deoxy-5-O-(4,4'-dimethoxytrityl)-β-D-ribofuranos-1-yl]-4-iodoimidazole
  参考文献：
  名称：

  Synthesis and Properties of Oligonucleotides with Iodo-Substituted Aromatic Aglycons:  Investigation of Possible Halogen Bonding Base Pairs

  摘要：

  [GRAPHICS]Ab initio calculations of halogen bond energies of artificial base pairs constructed between iodinated aromatic nucleobase mimics and nitrogen-containing acceptor molecules such as pyridine and imidazole suggest that modified base pairs are converted to optimized planar base pairs with weak Delta E values of -0.19 to -3.93 kcal/mol. To evaluate the contribution of halogen bonding toward duplex stabilization of such modified nucleobase mimics introduced into artificial base pairs, we synthesized three C-nucleoside analogues 1-3 with several iodinated aromatic rings and an imidazole nucleoside derivative 4 and incorporated them into oligodeoxynucleotides. Hybridization studies of modified oligodeoxynucleotides incorporating iodoaromatic bases showed their unique universal base-like ability; however, no indication of halogen bond formation was observed. A more sophisticated design is required for the development of new base pairs stabilized by halogen bonding.

  DOI：

  10.1021/jo701634t
• 作为产物：
  描述：

  1-(2-deoxy-β-D-ribofuranos-1-yl)-4,5-diiodoimidazole 、 4,4'-双甲氧基三苯甲基氯 在 吡啶 作用下， 反应 6.0h， 以86%的产率得到1-[2-deoxy-5-O-(4,4'-dimethoxytrityl)-β-D-ribofuranos-1-yl]-4,5-diiodoimidazole
  参考文献：
  名称：

  Synthesis and Properties of Oligonucleotides with Iodo-Substituted Aromatic Aglycons:  Investigation of Possible Halogen Bonding Base Pairs

  摘要：

  [GRAPHICS]Ab initio calculations of halogen bond energies of artificial base pairs constructed between iodinated aromatic nucleobase mimics and nitrogen-containing acceptor molecules such as pyridine and imidazole suggest that modified base pairs are converted to optimized planar base pairs with weak Delta E values of -0.19 to -3.93 kcal/mol. To evaluate the contribution of halogen bonding toward duplex stabilization of such modified nucleobase mimics introduced into artificial base pairs, we synthesized three C-nucleoside analogues 1-3 with several iodinated aromatic rings and an imidazole nucleoside derivative 4 and incorporated them into oligodeoxynucleotides. Hybridization studies of modified oligodeoxynucleotides incorporating iodoaromatic bases showed their unique universal base-like ability; however, no indication of halogen bond formation was observed. A more sophisticated design is required for the development of new base pairs stabilized by halogen bonding.

  DOI：

  10.1021/jo701634t