N-acetyl-L-alaninyl-L-(4-chloromethylcoumarin-6-yl)alanine methyl ester | 1449279-46-2

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: N-acetyl-L-alaninyl-L-(4-chloromethylcoumarin-6-yl)alanine methyl ester
• CAS: 1449279-46-2
• 化学式: C₁₉H₂₁ClN₂O₆
• 分子量: 408.839
• InChiKey: GBWUQNJRQSIPMS-BONVTDFDSA-N

物化性质

• 熔点：
  182-183.4 °C
• 沸点：
  697.1±55.0 °C(predicted)
• 密度：
  1.310±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.26
• 重原子数：
  28.0
• 可旋转键数：
  7.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.37
• 拓扑面积：
  114.71
• 氢给体数：
  2.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  N-乙酰-L-丙氨酸 、 N-acetyl-L-alaninyl-L-(4-chloromethylcoumarin-6-yl)alanine methyl ester 在 potassium fluoride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 48.0h， 以63%的产率得到methyl (S)-2-((S)-2-acetamidopropanamido)-3-(4-(((acetyl-L-alanyl)oxy)methyl)-2-oxo-2H-chromen-6-yl)propanoate
  参考文献：
  名称：

  A photoactivable amino acid based on a novel functional coumarin-6-yl-alanine

  摘要：

  A novel fluorescent amino acid, l-4-chloromethylcoumarin-6-yl-alanine, was obtained from tyrosine by a Pechmann reaction. The assembly of the heterocyclic ring at the tyrosine side chain could be achieved before or after incorporation of tyrosine into a dipeptide, and amino acid and dipeptide ester conjugates were obtained by coupling to a model N-protected alanine. The behaviour of one of the fluorescent conjugates towards irradiation was studied in a photochemical reactor at different wavelengths (254, 300, 350 and 419 nm). The photoreaction course in methanol/HEPES buffer solution (80:20) was followed by HPLC/UV monitoring. It was found that the novel unnatural amino acid could act as a fluorescent label, due to its fluorescence properties, and, more importantly, as a photoactivable unit, due to the short irradiation times necessary to cleave the ester bond between the model amino acid and the coumarin-6-yl-alanine.

  DOI：

  10.1007/s00726-012-1310-2
• 作为产物：
  描述：

  N-乙酰-L-丙氨酸 在 硫酸 、 1-羟基苯并三唑 、 N,N'-二环己基碳二亚胺 作用下， 以 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 528.0h， 生成 N-acetyl-L-alaninyl-L-(4-chloromethylcoumarin-6-yl)alanine methyl ester
  参考文献：
  名称：

  A photoactivable amino acid based on a novel functional coumarin-6-yl-alanine

  摘要：

  A novel fluorescent amino acid, l-4-chloromethylcoumarin-6-yl-alanine, was obtained from tyrosine by a Pechmann reaction. The assembly of the heterocyclic ring at the tyrosine side chain could be achieved before or after incorporation of tyrosine into a dipeptide, and amino acid and dipeptide ester conjugates were obtained by coupling to a model N-protected alanine. The behaviour of one of the fluorescent conjugates towards irradiation was studied in a photochemical reactor at different wavelengths (254, 300, 350 and 419 nm). The photoreaction course in methanol/HEPES buffer solution (80:20) was followed by HPLC/UV monitoring. It was found that the novel unnatural amino acid could act as a fluorescent label, due to its fluorescence properties, and, more importantly, as a photoactivable unit, due to the short irradiation times necessary to cleave the ester bond between the model amino acid and the coumarin-6-yl-alanine.

  DOI：

  10.1007/s00726-012-1310-2