N-(2-(2-(2-aminoethoxy)ethoxy)ethyl)-3,4,5-tris(2-(2-(2-azidoethoxy)ethoxy)ethoxy)benzamide | 1426561-76-3

• 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: N-(2-(2-(2-aminoethoxy)ethoxy)ethyl)-3,4,5-tris(2-(2-(2-azidoethoxy)ethoxy)ethoxy)benzamide
• CAS: 1426561-76-3
• 化学式: C₃₁H₅₃N₁₁O₁₂
• 分子量: 771.828
• InChiKey: MRMPJQZBECWZQZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.58
• 重原子数：
  54.0
• 可旋转键数：
  39.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.77
• 拓扑面积：
  302.93
• 氢给体数：
  2.0
• 氢受体数：
  16.0

反应信息

• 作为反应物：
  描述：

  异硫氰酸荧光素酯 、 N-(2-(2-(2-aminoethoxy)ethoxy)ethyl)-3,4,5-tris(2-(2-(2-azidoethoxy)ethoxy)ethoxy)benzamide 在 三乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以68%的产率得到
  参考文献：
  名称：

  Photoclickable Dendritic Molecular Glue: Noncovalent-to-Covalent Photochemical Transformation of Protein Hybrids

  摘要：

  A water-soluble dendron with a fluorescein isothiocyanate (FITC) fluorescent label and bearing nine pendant guanidinium ion (Gu(+))/benzophenone (BP) pairs at its periphery (Glue(BP)-FITC) serves as a "photo-clickable molecular glue". By multivalent salt-bride formation between Gu(+) ions and oxyanions, Glue(BP)-FITC temporarily adheres to a kinesin/microtubule hybrid. Upon subsequent exposure to UV light, this noncovalent binding is made permanent via a cross-linking reaction mediated by carbon radicals derived from the photoexcited BP units. This temporal-to-permanent transformation by light occurs quickly and efficiently in this preorganized state, allowing the movements of micro-tubules on a kinesin-coated glass plate to be photochemically controlled. A fundamental difference between such temporal and permanent bindings was visualized by the use of "optical tweezers".

  DOI：

  10.1021/ja401059w
• 作为产物：
  描述：

  1,8-二氨基-3,6-二氧杂辛烷 、 3,4,5-tris(2-(2-(2-azidoethoxy)ethoxy)ethoxy)benzoic acid 在 O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate 、 N,N-二异丙基乙胺 作用下， 以 乙腈 为溶剂， 反应 1.08h， 以40%的产率得到N-(2-(2-(2-aminoethoxy)ethoxy)ethyl)-3,4,5-tris(2-(2-(2-azidoethoxy)ethoxy)ethoxy)benzamide
  参考文献：
  名称：

  Photoclickable Dendritic Molecular Glue: Noncovalent-to-Covalent Photochemical Transformation of Protein Hybrids

  摘要：

  A water-soluble dendron with a fluorescein isothiocyanate (FITC) fluorescent label and bearing nine pendant guanidinium ion (Gu(+))/benzophenone (BP) pairs at its periphery (Glue(BP)-FITC) serves as a "photo-clickable molecular glue". By multivalent salt-bride formation between Gu(+) ions and oxyanions, Glue(BP)-FITC temporarily adheres to a kinesin/microtubule hybrid. Upon subsequent exposure to UV light, this noncovalent binding is made permanent via a cross-linking reaction mediated by carbon radicals derived from the photoexcited BP units. This temporal-to-permanent transformation by light occurs quickly and efficiently in this preorganized state, allowing the movements of micro-tubules on a kinesin-coated glass plate to be photochemically controlled. A fundamental difference between such temporal and permanent bindings was visualized by the use of "optical tweezers".

  DOI：

  10.1021/ja401059w