tert-butyl 2-(N-(2-((tert-butoxycarbonyl)amino)ethyl)-8-hydroxyquinoline-2-carboxamido)acetate | 1209466-36-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: tert-butyl 2-(N-(2-((tert-butoxycarbonyl)amino)ethyl)-8-hydroxyquinoline-2-carboxamido)acetate
• CAS: 1209466-36-3
• 化学式: C₂₃H₃₁N₃O₆
• 分子量: 445.516
• InChiKey: DKRYNJOTPVCQBY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.25
• 重原子数：
  32.0
• 可旋转键数：
  6.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.48
• 拓扑面积：
  118.06
• 氢给体数：
  2.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  tert-butyl 2-(N-(2-((tert-butoxycarbonyl)amino)ethyl)-8-hydroxyquinoline-2-carboxamido)acetate 在 sodium hydroxide 作用下， 以 乙醇 、 水 为溶剂， 以77%的产率得到2-(N-(2-((tert-butoxycarbonyl)amino)ethyl)-8-hydroxyquinoline-2-carboxamido)acetic acid
  参考文献：
  名称：

  Metal Binding to Ligand-Containing Peptide Nucleic Acids

  摘要：

  The substitution of nucleobases in nucleic acid duplexes with ligands that have high affinity for transition metal ions creates metal-binding sites at specific locations within the duplexes. Several studies on the incorporation of metal ions into DNA and peptide nucleic acid (PNA) duplexes have suggested that the stability constant of the metal complex formed within the duplexes is a primary determinant of the thermal stability of the duplexes. To understand this relationship, we have synthesized two PNA monomers that carry the same ligand, namely 8-hydroxyquinoline, but have this ligand attached differently to the PNA backbone. The PNA monomers have been incorporated into PNA duplexes. UV and CD spectroscopy and calorimetric studies of the 8-hydroxyquinoline-PNA duplexes showed that the effect of the stability of the metal complex on the PNA duplexes was significantly modulated by the steric relationship between the complex and the duplex. This information is useful for the construction of hybrid inorganic nucleic acid nanostructures.

  DOI：

  10.1021/ic200138b
• 作为产物：
  描述：

  8-羟基喹啉-2-羧酸 、 tert-butyl N-(2-Boc-aminoethyl)glycinate 在 3-羟基-1,2,3-苯并三嗪-4(3H)-酮 、 N,N'-二环己基碳二亚胺 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 26.0h， 以51%的产率得到tert-butyl 2-(N-(2-((tert-butoxycarbonyl)amino)ethyl)-8-hydroxyquinoline-2-carboxamido)acetate
  参考文献：
  名称：

  Metal Binding to Ligand-Containing Peptide Nucleic Acids

  摘要：

  The substitution of nucleobases in nucleic acid duplexes with ligands that have high affinity for transition metal ions creates metal-binding sites at specific locations within the duplexes. Several studies on the incorporation of metal ions into DNA and peptide nucleic acid (PNA) duplexes have suggested that the stability constant of the metal complex formed within the duplexes is a primary determinant of the thermal stability of the duplexes. To understand this relationship, we have synthesized two PNA monomers that carry the same ligand, namely 8-hydroxyquinoline, but have this ligand attached differently to the PNA backbone. The PNA monomers have been incorporated into PNA duplexes. UV and CD spectroscopy and calorimetric studies of the 8-hydroxyquinoline-PNA duplexes showed that the effect of the stability of the metal complex on the PNA duplexes was significantly modulated by the steric relationship between the complex and the duplex. This information is useful for the construction of hybrid inorganic nucleic acid nanostructures.

  DOI：

  10.1021/ic200138b