1-(3',5'-di-O-p-toluoyl-2'-deoxy-β-D-ribofuranosyl)-3-cyanopyrrole | 110089-37-7

• 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: 1-(3',5'-di-O-p-toluoyl-2'-deoxy-β-D-ribofuranosyl)-3-cyanopyrrole
• 英文别名: [(2R,3S,5R)-5-(3-cyanopyrrol-1-yl)-3-(4-methylbenzoyl)oxyoxolan-2-yl]methyl 4-methylbenzoate
• CAS: 110089-37-7
• 化学式: C₂₆H₂₄N₂O₅
• 分子量: 444.487
• InChiKey: GLYXVMLPFFAKIM-RBZQAINGSA-N

物化性质

• 沸点：
  624.4±55.0 °C(Predicted)
• 密度：
  1.24±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  33
• 可旋转键数：
  8
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  90.6
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  1-(3',5'-di-O-p-toluoyl-2'-deoxy-β-D-ribofuranosyl)-3-cyanopyrrole 在 磷酸三甲酯 、 ammonium hydroxide 、 磷酸三乙酯 、 双氧水 、 三乙胺 、 三氯氧磷 作用下， 以 1,4-二氧六环 、 甲醇 为溶剂， 反应 13.08h， 生成 1-(2'-deoxy-β-D-ribofuranosyl)-pyrrole-3-carboxamide-5'-triphosphate
  参考文献：
  名称：

  Synthesis and Incorporation of Pyrrole Carboxamide Nucleoside Triphosphates by DNA Polymerases

  摘要：

  We have synthesised and examined the enzymatic incorporation properties of the 5'-triphosphates of 2'-deoxyribosyl pyrrole 3-monocarboxamide (dMTP) and 2'-deoxyribosyl pyrrole 3,4-dicarboxamide (dDTP). These analogues we had hoped would behave as ambivalent base analogues in that they can present two alternative hydrogen-bonding faces either by rotation about the carboxamide group or about the glycosidic bond. The two pyrrole derivatives, dMTP and dDTP, exhibit a preference for incorporation with Klenow polymerase. They are preferentially incorporated as either A or C.

  DOI：

  10.1080/15257770008045449
• 作为产物：
  描述：

  Hoffer's chlorosugar 、 3-氰基吡咯 在 sodium hydride 作用下， 以 乙腈 为溶剂， 反应 2.5h， 以87%的产率得到1-(3',5'-di-O-p-toluoyl-2'-deoxy-β-D-ribofuranosyl)-3-cyanopyrrole
  参考文献：
  名称：

  Synthesis and Incorporation of Pyrrole Carboxamide Nucleoside Triphosphates by DNA Polymerases

  摘要：

  We have synthesised and examined the enzymatic incorporation properties of the 5'-triphosphates of 2'-deoxyribosyl pyrrole 3-monocarboxamide (dMTP) and 2'-deoxyribosyl pyrrole 3,4-dicarboxamide (dDTP). These analogues we had hoped would behave as ambivalent base analogues in that they can present two alternative hydrogen-bonding faces either by rotation about the carboxamide group or about the glycosidic bond. The two pyrrole derivatives, dMTP and dDTP, exhibit a preference for incorporation with Klenow polymerase. They are preferentially incorporated as either A or C.

  DOI：

  10.1080/15257770008045449

文献信息

• Synthesis and Incorporation of Pyrrole Carboxamide Nucleoside Triphosphates by DNA Polymerases
  作者：D. Loakes、M. J. Guo、D. M. Brown、S. A. Salisbury、C. L. Smith、I. Felix、S. Kumar、S. Nampalli

  DOI：10.1080/15257770008045449

  日期：2000.10

  We have synthesised and examined the enzymatic incorporation properties of the 5'-triphosphates of 2'-deoxyribosyl pyrrole 3-monocarboxamide (dMTP) and 2'-deoxyribosyl pyrrole 3,4-dicarboxamide (dDTP). These analogues we had hoped would behave as ambivalent base analogues in that they can present two alternative hydrogen-bonding faces either by rotation about the carboxamide group or about the glycosidic bond. The two pyrrole derivatives, dMTP and dDTP, exhibit a preference for incorporation with Klenow polymerase. They are preferentially incorporated as either A or C.