methyl (3S,E)-3-(4-((4-(2,2,-dimethyl-6,9,12,15,18-pentaoxanonadeca-1,18-diynyl)phenyl)diazenyl)benzamido)-2-hydroxy-4-phenylbutanoate | 1001073-67-1

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二芳基庚烷
• 英文名称: methyl (3S,E)-3-(4-((4-(2,2,-dimethyl-6,9,12,15,18-pentaoxanonadeca-1,18-diynyl)phenyl)diazenyl)benzamido)-2-hydroxy-4-phenylbutanoate
• CAS: 1001073-67-1
• 化学式: C₃₇H₄₀F₃N₃O₇
• 分子量: 695.736
• InChiKey: JOOPEBNEZGLAGP-IBSIFDLTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.43
• 重原子数：
  50.0
• 可旋转键数：
  21.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  120.2
• 氢给体数：
  2.0
• 氢受体数：
  9.0

反应信息

• 作为反应物：
  描述：

  methyl (3S,E)-3-(4-((4-(2,2,-dimethyl-6,9,12,15,18-pentaoxanonadeca-1,18-diynyl)phenyl)diazenyl)benzamido)-2-hydroxy-4-phenylbutanoate 在 戴斯-马丁氧化剂 作用下， 以 二氯甲烷 为溶剂， 反应 3.0h， 以90%的产率得到methyl (3S,E)-3-(4-((4-(2,2,-dimethyl-6,9,12,15,18-pentaoxanonadeca-1,18-diynyl)phenyl)diazenyl)benzamido)-2-oxo-4-phenylbutanoate
  参考文献：
  名称：

  Reversible Photoregulation of Binding of α-Chymotrypsin to a Gold Surface

  摘要：

  An ability to optically modulate the interactions of surfaces with functional biomolecules provides an important basis for generating new technologies including reversible biosensors, advanced medical implants, and biomolecular computers. Here we report the first example of reversible photoregulation of binding of a protease to a functional surface. A modular approach is presented with a surface-bound inhibitor containing a photoisomerizable azobenzene core to which is attached (i) appropriate protease binding functionality and (ii) a tether for surface attachment. The principle is demonstrated for M-chymotrypsin using a phenylalanine-based trifluoromethyl ketone inhibitor containing an azobenzene core and an alkyne-functionalized ethylene glycol tether, which is attached to the surface using click chemistry, UV/vis irradiation of the functional surface leads to a significant, reversible change in the amount of alpha-chymotrypsin that attaches to the surface, as measured by surface plasmon resonance.

  DOI：

  10.1021/ja0766674
• 作为产物：
  描述：

  (E)-4-((4-(4,7,10,13,16-pentaoxanonadeca-1,18-diynyl)phenyl)diazenyl)benzoic acid 、 (3S)-3-amino-1,1,1-trifluoro-4-phenylbutan-2-ol 在 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 N,N-二异丙基乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 19.0h， 以80%的产率得到methyl (3S,E)-3-(4-((4-(2,2,-dimethyl-6,9,12,15,18-pentaoxanonadeca-1,18-diynyl)phenyl)diazenyl)benzamido)-2-hydroxy-4-phenylbutanoate
  参考文献：
  名称：

  Reversible Photoregulation of Binding of α-Chymotrypsin to a Gold Surface

  摘要：

  An ability to optically modulate the interactions of surfaces with functional biomolecules provides an important basis for generating new technologies including reversible biosensors, advanced medical implants, and biomolecular computers. Here we report the first example of reversible photoregulation of binding of a protease to a functional surface. A modular approach is presented with a surface-bound inhibitor containing a photoisomerizable azobenzene core to which is attached (i) appropriate protease binding functionality and (ii) a tether for surface attachment. The principle is demonstrated for M-chymotrypsin using a phenylalanine-based trifluoromethyl ketone inhibitor containing an azobenzene core and an alkyne-functionalized ethylene glycol tether, which is attached to the surface using click chemistry, UV/vis irradiation of the functional surface leads to a significant, reversible change in the amount of alpha-chymotrypsin that attaches to the surface, as measured by surface plasmon resonance.

  DOI：

  10.1021/ja0766674