benzyl tert-butyl (7,10-bis(2-(((benzyloxy)carbonyl)amino)ethyl)-3-oxo-1-phenyl-2-oxa-4,7,10-triazahexadecane-12,16-diyl)(S)-dicarbamate | 1028803-13-5

• 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: benzyl tert-butyl (7,10-bis(2-(((benzyloxy)carbonyl)amino)ethyl)-3-oxo-1-phenyl-2-oxa-4,7,10-triazahexadecane-12,16-diyl)(S)-dicarbamate
• CAS: 1028803-13-5
• 化学式: C₅₁H₆₉N₇O₁₀
• 分子量: 940.15
• InChiKey: OXZHQBHFGSAPPA-GWHBCOKCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.36
• 重原子数：
  68.0
• 可旋转键数：
  28.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  198.13
• 氢给体数：
  5.0
• 氢受体数：
  12.0

反应信息

• 作为反应物：
  描述：

  benzyl tert-butyl (7,10-bis(2-(((benzyloxy)carbonyl)amino)ethyl)-3-oxo-1-phenyl-2-oxa-4,7,10-triazahexadecane-12,16-diyl)(S)-dicarbamate 在 5% Pd(II)/C(eggshell) 、 氢气 作用下， 以 甲醇 为溶剂， 生成 (S)-(tert-butyl) 5-amino-6-((2-aminoethyl)(2-(bis(2-aminoethyl)amino)ethyl)amino)hexylcarbamate
  参考文献：
  名称：

  Eu(III) Complexes of Functionalized Octadentate 1-Hydroxypyridin-2-ones: Stability, Bioconjugation, and Luminescence Resonance Energy Transfer Studies

  摘要：

  The synthesis, stability, and photophysical properties of several Eu(III) complexes featuring the 1-hydroxypyridin-2-one (1,2-HOPO) chelate group in tetradentate and octadentate ligands are reported. These complexes pair highly efficient emission with exceptional stabilities (pEu similar to 20.7-21.8) in aqueous solution at pH 7.4. Further analysis of their solution behavior has shown the observed luminescence intensity is significantly diminished below about pH similar to 6 because of an apparent quenching mechanism involving protonation of the amine backbones. Nonetheless, under biologically relevant conditions, these complexes are promising candidates for applications in Homogeneous Time-Resolved Fluorescence (HTRF) assays and synthetic methodology to prepare derivatives with either a terminal amine or a carboxylate group suitable for bioconjugation has been developed. Lastly, we have demonstrated the use of these compounds as the energy donor in a Luminescence Resonance Energy Transfer (LRET) biological assay format.

  DOI：

  10.1021/ic101133w
• 作为产物：
  描述：

  N-Cbz-氮丙啶 、 benzyl tert-butyl (7-(2-(((benzyloxy)carbonyl)amino)ethyl)-3-oxo-1-phenyl-2-oxa-4,7,10-triazahexadecane-12,16-diyl)(S)-dicarbamate 以 叔丁醇 为溶剂， 反应 16.0h， 以84.7%的产率得到benzyl tert-butyl (7,10-bis(2-(((benzyloxy)carbonyl)amino)ethyl)-3-oxo-1-phenyl-2-oxa-4,7,10-triazahexadecane-12,16-diyl)(S)-dicarbamate
  参考文献：
  名称：

  Eu(III) Complexes of Functionalized Octadentate 1-Hydroxypyridin-2-ones: Stability, Bioconjugation, and Luminescence Resonance Energy Transfer Studies

  摘要：

  The synthesis, stability, and photophysical properties of several Eu(III) complexes featuring the 1-hydroxypyridin-2-one (1,2-HOPO) chelate group in tetradentate and octadentate ligands are reported. These complexes pair highly efficient emission with exceptional stabilities (pEu similar to 20.7-21.8) in aqueous solution at pH 7.4. Further analysis of their solution behavior has shown the observed luminescence intensity is significantly diminished below about pH similar to 6 because of an apparent quenching mechanism involving protonation of the amine backbones. Nonetheless, under biologically relevant conditions, these complexes are promising candidates for applications in Homogeneous Time-Resolved Fluorescence (HTRF) assays and synthetic methodology to prepare derivatives with either a terminal amine or a carboxylate group suitable for bioconjugation has been developed. Lastly, we have demonstrated the use of these compounds as the energy donor in a Luminescence Resonance Energy Transfer (LRET) biological assay format.

  DOI：

  10.1021/ic101133w