7-(2,2'-bithien-5-yl)-3-(2-deoxy-3,5-di-O-(p-toluoyl)-beta-D-ribofuranosyl)imidazo[4,5-b]pyridine | 1222200-97-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 7-(2,2'-bithien-5-yl)-3-(2-deoxy-3,5-di-O-(p-toluoyl)-beta-D-ribofuranosyl)imidazo[4,5-b]pyridine
• CAS: 1222200-97-6
• 化学式: C₃₅H₂₉N₃O₅S₂
• 分子量: 635.764
• InChiKey: VMVDWCAHSYNVKK-SWFBWHSRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.88
• 重原子数：
  45.0
• 可旋转键数：
  8.0
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  92.54
• 氢给体数：
  0.0
• 氢受体数：
  10.0

反应信息

• 作为反应物：
  描述：

  7-(2,2'-bithien-5-yl)-3-(2-deoxy-3,5-di-O-(p-toluoyl)-beta-D-ribofuranosyl)imidazo[4,5-b]pyridine 在 甲醇 、 sodium methylate 作用下， 以 二氯甲烷 为溶剂， 反应 0.5h， 以90 mg的产率得到7-(2,2'-bithien-5-yl)-3-(2-deoxy-β-D-ribofuranosyl)imidazo[4,5-b]pyridine
  参考文献：
  名称：

  A Unique Fluorescent Base Analogue for the Expansion of the Genetic Alphabet

  摘要：

  Fluorescent nucleobase analogues are useful in a wide variety of biology and biotechnology tools as molecular probes and reporters for nucleic acids. Here we present a novel fluorescent purine analogue, 7-(2,2'-bithien-5-yl)-imidazo[4,5-b]pyridine (denoted as Dss). The nucleoside triphosphates of Dss can be site-specifically incorporated into DNA and RNA by polymerases, opposite its pairing partner, pyrrole-2-carbaldehyde (Pa), in DNA templates. Despite its high specificity in replication and transcription, Dss in oligonucleotides functions as a universal base that pairs with all four natural bases with nearly equal thermal stabilities. Thus, Dss would be a powerful tool for fluorescent base replacements at specific positions in functional DNA and RNA molecules.

  DOI：

  10.1021/ja100806c
• 作为产物：
  描述：

  2-deoxy-3,5-di-O-(p-toluoyl)-α-D-erythropentofuranosyl chloride 、 7-(2,2'-bithien-5-yl)-3H-imidazo[4,5-b]pyridine 在 sodium hydride 作用下， 以 乙腈 、 mineral oil 为溶剂， 反应 12.0h， 以227 mg的产率得到7-(2,2'-bithien-5-yl)-3-(2-deoxy-3,5-di-O-(p-toluoyl)-beta-D-ribofuranosyl)imidazo[4,5-b]pyridine
  参考文献：
  名称：

  A Unique Fluorescent Base Analogue for the Expansion of the Genetic Alphabet

  摘要：

  Fluorescent nucleobase analogues are useful in a wide variety of biology and biotechnology tools as molecular probes and reporters for nucleic acids. Here we present a novel fluorescent purine analogue, 7-(2,2'-bithien-5-yl)-imidazo[4,5-b]pyridine (denoted as Dss). The nucleoside triphosphates of Dss can be site-specifically incorporated into DNA and RNA by polymerases, opposite its pairing partner, pyrrole-2-carbaldehyde (Pa), in DNA templates. Despite its high specificity in replication and transcription, Dss in oligonucleotides functions as a universal base that pairs with all four natural bases with nearly equal thermal stabilities. Thus, Dss would be a powerful tool for fluorescent base replacements at specific positions in functional DNA and RNA molecules.

  DOI：

  10.1021/ja100806c