N-[2-(fluorenylmethoxycarbonyl)aminoethyl]-N-[2-(6-(2-(3-(tert-butyloxycarbonylamino)-propoxy)phenyl)-3H-pyrrolo[2,3-d]pyrimidin-2(7H)-on-3-yl)acetyl]glycine | 1192364-80-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 芴
• 英文名称: N-[2-(fluorenylmethoxycarbonyl)aminoethyl]-N-[2-(6-(2-(3-(tert-butyloxycarbonylamino)-propoxy)phenyl)-3H-pyrrolo[2,3-d]pyrimidin-2(7H)-on-3-yl)acetyl]glycine
• 英文别名: 2-[2-(9H-fluoren-9-ylmethoxycarbonylamino)ethyl-[2-[6-[2-[3-[(2-methylpropan-2-yl)oxycarbonylamino]propoxy]phenyl]-2-oxo-7H-pyrrolo[2,3-d]pyrimidin-3-yl]acetyl]amino]acetic acid
• CAS: 1192364-80-9
• 化学式: C₄₁H₄₄N₆O₉
• 分子量: 764.835
• InChiKey: CMCGWMRBBAONGE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  56
• 可旋转键数：
  18
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  188
• 氢给体数：
  4
• 氢受体数：
  9

反应信息

• 作为产物：
  描述：

  benzyl N-[2-(fluorenylmethoxycarbonyl)aminoethyl]-N-[2-(6-(2-(3-(tertbutyloxycarbonylamino)propoxy)phenyl)-3H-pyrrolo[2,3-d]pyrimidin-2(7H)-on-3-yl)acetyl]glycinate 在 palladium on activated charcoal 、 氢气 作用下， 以 甲醇 为溶剂， 反应 2.0h， 以80%的产率得到N-[2-(fluorenylmethoxycarbonyl)aminoethyl]-N-[2-(6-(2-(3-(tert-butyloxycarbonylamino)-propoxy)phenyl)-3H-pyrrolo[2,3-d]pyrimidin-2(7H)-on-3-yl)acetyl]glycine
  参考文献：
  名称：

  Peptide Nucleic Acid Containing a Meta-Substituted Phenylpyrrolocytosine Exhibits a Fluorescence Response and Increased Binding Affinity toward RNA

  摘要：

  Peptide nucleic acids (PNA) containing meta-substituted 6-phenylpyrrolocytosine (PhpC), [mono-m)-(aminoethoxy)phenyl]pyrrolocytosine (mmePhpC), [mono-m-(aminopropoxy)phenyl]pyrrolocytosine (mmpPhpC), and [mono-m-(guanidinoethoxy)phenyl]pyrrolocytosine (mmguaPhpC), have been synthesized. Meta-substituted PhpCs have been hybridized with overall higher binding affinity toward DNA and RNA than previously synthesized moePhpC or newly synthesized mopPhpC. The guanidinium-containing nucleobase, mmguaPhpC, exhibited the highest increase in binding affinity toward RNA while fluorometrically responding on the state of hybridization.

  DOI：

  10.1021/ol9019474

文献信息

• Peptide Nucleic Acid Containing a Meta-Substituted Phenylpyrrolocytosine Exhibits a Fluorescence Response and Increased Binding Affinity toward RNA
  作者：Filip Wojciechowski、Robert H. E. Hudson

  DOI：10.1021/ol9019474

  日期：2009.11.5

  Peptide nucleic acids (PNA) containing meta-substituted 6-phenylpyrrolocytosine (PhpC), [mono-m)-(aminoethoxy)phenyl]pyrrolocytosine (mmePhpC), [mono-m-(aminopropoxy)phenyl]pyrrolocytosine (mmpPhpC), and [mono-m-(guanidinoethoxy)phenyl]pyrrolocytosine (mmguaPhpC), have been synthesized. Meta-substituted PhpCs have been hybridized with overall higher binding affinity toward DNA and RNA than previously synthesized moePhpC or newly synthesized mopPhpC. The guanidinium-containing nucleobase, mmguaPhpC, exhibited the highest increase in binding affinity toward RNA while fluorometrically responding on the state of hybridization.