(R)-2-(N-(2-(((9H-fluoren-9-yl)methoxy)carbonylamino)-5-tert-butoxy-5-oxopentyl)-2-(thymin-1(2H)-yl)acetamido)acetic acid | 1018907-58-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 芴
• 英文名称: (R)-2-(N-(2-(((9H-fluoren-9-yl)methoxy)carbonylamino)-5-tert-butoxy-5-oxopentyl)-2-(thymin-1(2H)-yl)acetamido)acetic acid
• CAS: 1018907-58-8
• 化学式: C₃₃H₃₈N₄O₉
• 分子量: 634.686
• InChiKey: QJZFJLHTIZYHET-OAQYLSRUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.79
• 重原子数：
  46.0
• 可旋转键数：
  12.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.39
• 拓扑面积：
  177.1
• 氢给体数：
  3.0
• 氢受体数：
  9.0

反应信息

• 作为产物：
  描述：

  在 palladium on activated charcoal 氢气 作用下， 以 甲醇 为溶剂， 生成 (R)-2-(N-(2-(((9H-fluoren-9-yl)methoxy)carbonylamino)-5-tert-butoxy-5-oxopentyl)-2-(thymin-1(2H)-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

文献信息

• Synthesis of Enantiopure γ-Glutamic Acid Functionalized Peptide Nucleic Acid Monomers
  作者：Hu Huang、Goon-Ho Joe、Sung-Rok Choi、Su-Nam Kim、Yong-Tae Kim、Chwang-Siek Pak、Joon-Hee Hong、Won-Jae Lee

  DOI：10.5012/bkcs.2010.31.7.2054

  日期：2010.7.20