(S)-allyl 2-(N-(2-(((9H-fluoren-9-yl)methoxy)carbonylamino)-6-(tert-butoxycarbonylamino)hexyl)-2-(2-(benzhydryloxycarbonylamino)-guanin-9-yl)acetamido)acetate | 1018907-31-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 芴
• 英文名称: (S)-allyl 2-(N-(2-(((9H-fluoren-9-yl)methoxy)carbonylamino)-6-(tert-butoxycarbonylamino)hexyl)-2-(2-(benzhydryloxycarbonylamino)-guanin-9-yl)acetamido)acetate
• CAS: 1018907-31-7
• 化学式: C₅₂H₅₆N₈O₁₀
• 分子量: 953.064
• InChiKey: GTEPZSKLBIIXNZ-BHVANESWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.62
• 重原子数：
  70.0
• 可旋转键数：
  20.0
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  225.17
• 氢给体数：
  4.0
• 氢受体数：
  13.0

反应信息

• 作为反应物：
  描述：

  (S)-allyl 2-(N-(2-(((9H-fluoren-9-yl)methoxy)carbonylamino)-6-(tert-butoxycarbonylamino)hexyl)-2-(2-(benzhydryloxycarbonylamino)-guanin-9-yl)acetamido)acetate 在 四(三苯基膦)钯 N-ethyl aniline 作用下， 以 四氢呋喃 为溶剂， 反应 1.0h， 以68%的产率得到(S)-2-(N-(2-(((9H-fluoren-9-yl)methoxy)carbonylamino)-6-(tert-butoxycarbonylamino)hexyl)-2-(2-(benzhydryloxycarbonylamino)-guanin-9-yl)acetamido)acetic acid
  参考文献：
  名称：

  DNA-Templated Polymerization of Side-Chain-Functionalized Peptide Nucleic Acid Aldehydes

  摘要：

  The DNA-templated polymerization of synthetic building blocks provides a potential route to the laboratory evolution of sequence-defined polymers with structures and properties not necessarily limited to those of natural biopolymers. We previously reported the efficient and sequence-specific DNA-templated polymerization of peptide nucleic acid (PNA) aldehydes. Here, we report the enzyme-free, DNA-templated polymerization of side-chain-functionalized PNA tetramer and pentamer aldehydes. We observed that polymerization of tetramer and pentamer PNA building blocks with a single lysine-based side chain at various positions in the building block could proceed efficiently and sequence specifically. In addition, DNA-templated polymerization also proceeded efficiently and in a sequence-specific manner with pentamer PNA aldehydes containing two or three lysine side chains in a single building block to generate more densely functionalized polymers. To further our understanding of side-chain compatibility and expand the capabilities of this system, we also examined the polymerization efficiencies of 20 pentamer building blocks each containing one of five different side-chain groups and four different side-chain regio- and stereochemistries. Polymerization reactions were efficient for all five different side-chain groups and for three of the four combinations of side-chain regio- and stereochemistries. Differences in the efficiency and initial rate of polymerization correlate with the apparent melting temperature of each building block, which is dependent on side-chain regio- and stereochemistry but relatively insensitive to side-chain structure among the substrates tested. Our findings represent a significant step toward the evolution of sequence-defined synthetic polymers and also demonstrate that enzyme-free nucleic acid-templated polymerization can occur efficiently using substrates with a wide range of side-chain structures, functionalization positions within each building block, and functionalization densities.

  DOI：

  10.1021/ja0753997
• 作为产物：
  描述：

  (S)-allyl 2-((2-((((9H-fluoren-9-yl)methoxy)carbonyl) amino)-6-((tert-butoxycarbonyl)amino)hexyl)amino)acetate 、 (2-二苯甲基氧基羰基氨基-6-氧代-1,6-二氢嘌呤-9-基)-乙酸 在 (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate 、 1-羟基苯并三唑 、 N,N-二异丙基乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 6.0h， 以37.2%的产率得到(S)-allyl 2-(N-(2-(((9H-fluoren-9-yl)methoxy)carbonylamino)-6-(tert-butoxycarbonylamino)hexyl)-2-(2-(benzhydryloxycarbonylamino)-guanin-9-yl)acetamido)acetate
  参考文献：
  名称：

  DNA-Templated Polymerization of Side-Chain-Functionalized Peptide Nucleic Acid Aldehydes

  摘要：

  The DNA-templated polymerization of synthetic building blocks provides a potential route to the laboratory evolution of sequence-defined polymers with structures and properties not necessarily limited to those of natural biopolymers. We previously reported the efficient and sequence-specific DNA-templated polymerization of peptide nucleic acid (PNA) aldehydes. Here, we report the enzyme-free, DNA-templated polymerization of side-chain-functionalized PNA tetramer and pentamer aldehydes. We observed that polymerization of tetramer and pentamer PNA building blocks with a single lysine-based side chain at various positions in the building block could proceed efficiently and sequence specifically. In addition, DNA-templated polymerization also proceeded efficiently and in a sequence-specific manner with pentamer PNA aldehydes containing two or three lysine side chains in a single building block to generate more densely functionalized polymers. To further our understanding of side-chain compatibility and expand the capabilities of this system, we also examined the polymerization efficiencies of 20 pentamer building blocks each containing one of five different side-chain groups and four different side-chain regio- and stereochemistries. Polymerization reactions were efficient for all five different side-chain groups and for three of the four combinations of side-chain regio- and stereochemistries. Differences in the efficiency and initial rate of polymerization correlate with the apparent melting temperature of each building block, which is dependent on side-chain regio- and stereochemistry but relatively insensitive to side-chain structure among the substrates tested. Our findings represent a significant step toward the evolution of sequence-defined synthetic polymers and also demonstrate that enzyme-free nucleic acid-templated polymerization can occur efficiently using substrates with a wide range of side-chain structures, functionalization positions within each building block, and functionalization densities.

  DOI：

  10.1021/ja0753997