7-(2,2'-bithien-5-yl)-3-(β-D-ribofuranosyl)imidazo[4,5-b]pyridine 5'-triphosphate | 1222201-14-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 7-(2,2'-bithien-5-yl)-3-(β-D-ribofuranosyl)imidazo[4,5-b]pyridine 5'-triphosphate
• 英文别名: [[(2R,3S,4R,5R)-3,4-dihydroxy-5-[7-(5-thiophen-2-ylthiophen-2-yl)imidazo[4,5-b]pyridin-3-yl]oxolan-2-yl]methoxy-hydroxyphosphoryl] phosphono hydrogen phosphate
• CAS: 1222201-14-0
• 化学式: C₁₉H₂₀N₃O₁₃P₃S₂
• 分子量: 655.433
• InChiKey: PUEZBDLQZOYQNY-ZSDNKIRRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -2
• 重原子数：
  40
• 可旋转键数：
  10
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  297
• 氢给体数：
  6
• 氢受体数：
  17

反应信息

• 作为产物：
  描述：

  7-(2,2'-bithien-5-yl)-3-(2,3-di-O-acetyl-β-D-ribofuranosyl)imidazo[4,5-b]pyridine 在 吡啶 、 2-氯-1,3,2-苯并二氧磷杂环己烷-4-酮 、 三正丁胺 、 三丁基焦磷酸铵 作用下， 以 1,4-二氧六环 、 N,N-二甲基甲酰胺 为溶剂， 反应 0.17h， 以26%的产率得到7-(2,2'-bithien-5-yl)-3-(β-D-ribofuranosyl)imidazo[4,5-b]pyridine 5'-triphosphate
  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

文献信息

• ARTIFICIAL BASE PAIR CAPABLE OF FORMING SPECIFIC BASE PAIR
  申请人：Hirao Ichiro

  公开号：US20120231462A1

  公开（公告）日：2012-09-13

  The present invention provides a double-stranded nucleic acid in which at least one nucleic acid strand includes an unnatural base that forms a self-complementary base pair or an unnatural base that forms a base pair with any natural base with substantially the same thermal stability. The present invention also provides a method of hybridizing a first nucleic acid strand with a second nucleic acid strand, wherein the first nucleic acid strand includes an unnatural base that forms a self-complementary base pair or an unnatural base that forms a base pair with any natural base with substantially the same thermal stability, and a method of applying the nucleic acid to SNP detection, a DNA chip, DNA/RNA computing, or an in vitro translation system. The present invention provides a method of introducing an unnatural base into a nucleic acid strand and thereby controlling the thermodynamic stability in hybridization of the nucleic acid strand.

  本发明提供一种双链核酸，其中至少一个核酸链包括一种不自然碱基，该碱基形成自补碱基对或与任何天然碱基形成具有基本相同热稳定性的碱基对。本发明还提供了一种将第一核酸链与第二核酸链杂交的方法，其中第一核酸链包括一种形成自补碱基对或与任何天然碱基形成具有基本相同热稳定性的不自然碱基，以及将该核酸应用于SNP检测、DNA芯片、DNA/RNA计算或体外翻译系统的方法。本发明提供了一种将不自然碱基引入核酸链中并从而控制核酸链杂交的热力学稳定性的方法。
• NOVEL ARTIFICIAL FLUORESCENT BASES
  申请人：Riken

  公开号：EP2487180B1

  公开（公告）日：2014-12-03
• US8895712B2
  申请人：——

  公开号：US8895712B2

  公开（公告）日：2014-11-25
• A Unique Fluorescent Base Analogue for the Expansion of the Genetic Alphabet
  作者：Michiko Kimoto、Tsuneo Mitsui、Shigeyuki Yokoyama、Ichiro Hirao

  DOI：10.1021/ja100806c

  日期：2010.4.14

  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.