tert-butyl (S)-(5-(1-(benzyloxy)-6-oxo-1,6-dihydropyridine-2-carboxamido)-6-((2-(1-(benzyloxy)-6-oxo-1,6-dihydropyridine-2-carboxamido)ethyl)(2-(bis(2-(1-(benzyloxy)-6-oxo-1,6-dihydropyridine-2-carboxamido)ethyl)amino)ethyl)amino)hexyl)carbamate | 1253698-21-3

• 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: tert-butyl (S)-(5-(1-(benzyloxy)-6-oxo-1,6-dihydropyridine-2-carboxamido)-6-((2-(1-(benzyloxy)-6-oxo-1,6-dihydropyridine-2-carboxamido)ethyl)(2-(bis(2-(1-(benzyloxy)-6-oxo-1,6-dihydropyridine-2-carboxamido)ethyl)amino)ethyl)amino)hexyl)carbamate
• CAS: 1253698-21-3
• 化学式: C₇₁H₈₁N₁₁O₁₄
• 分子量: 1312.49
• InChiKey: JAWFUGYCNVQOJS-SMWREMLRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.54
• 重原子数：
  96.0
• 可旋转键数：
  36.0
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  286.13
• 氢给体数：
  5.0
• 氢受体数：
  20.0

反应信息

• 作为反应物：
  描述：

  tert-butyl (S)-(5-(1-(benzyloxy)-6-oxo-1,6-dihydropyridine-2-carboxamido)-6-((2-(1-(benzyloxy)-6-oxo-1,6-dihydropyridine-2-carboxamido)ethyl)(2-(bis(2-(1-(benzyloxy)-6-oxo-1,6-dihydropyridine-2-carboxamido)ethyl)amino)ethyl)amino)hexyl)carbamate 在 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 4.0h， 生成
  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：

  (S)-(tert-butyl) 5-amino-6-((2-aminoethyl)(2-(bis(2-aminoethyl)amino)ethyl)amino)hexylcarbamate 、 1-(benzyloxy)-6-oxo-1,6-dihydropyridine-2-carbonyl chloride 在 potassium carbonate 作用下， 以 二氯甲烷 为溶剂， 以70%的产率得到tert-butyl (S)-(5-(1-(benzyloxy)-6-oxo-1,6-dihydropyridine-2-carboxamido)-6-((2-(1-(benzyloxy)-6-oxo-1,6-dihydropyridine-2-carboxamido)ethyl)(2-(bis(2-(1-(benzyloxy)-6-oxo-1,6-dihydropyridine-2-carboxamido)ethyl)amino)ethyl)amino)hexyl)carbamate
  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