(S)-2-((S)-2-(2-aminoacetoxy)-4-methylpentanamido)-4-(methylthio)butanoic acid hydrochloride | 1578264-26-2

• 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: (S)-2-((S)-2-(2-aminoacetoxy)-4-methylpentanamido)-4-(methylthio)butanoic acid hydrochloride
• CAS: 1578264-26-2
• 化学式: C₁₃H₂₄N₂O₅S*ClH
• 分子量: 356.871
• InChiKey: YNKXCHZDXHEFNX-IYPAPVHQSA-N

物化性质

• 熔点：
  104-107 °C

计算性质

• 辛醇/水分配系数(LogP)：
  0.65
• 重原子数：
  22.0
• 可旋转键数：
  10.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.77
• 拓扑面积：
  118.72
• 氢给体数：
  3.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  N-(7-methoxycoumarin-3-ylcarbonyl)benzotriazole 、 (S)-2-((S)-2-(2-aminoacetoxy)-4-methylpentanamido)-4-(methylthio)butanoic acid hydrochloride 在 三乙胺 作用下， 以 水 、 乙腈 为溶剂， 反应 1.0h， 以92%的产率得到(S)-2-((S)-2-(2-(7-methoxy-2-oxo-2H-chromene-3-carboxamido)acetoxy)-4-methylpentanamido)-4-(methylthio)butanoic acid
  参考文献：
  名称：

  Photophysics of novel coumarin-labeled depsipeptides in solution: sensing interactions with SDS micelle via TICT model

  摘要：

  N-Acylbenzotriazoles enable the synthesis (69-92 % yield) of blue to green fluorescent coumarin-labeled depsidipeptides 8a-f (quantum yields 0.004-0.97) and depsitripeptides 12a-d (quantum yields 0.02-0.96). Detailed photophysical studies of fluorescent coumarin-labeled depsipeptides 8a-f and 12a-d are reported for both polar protic and polar aprotic solvents. 7-Methoxy and 7-diethylaminocoumarin-3-ylcarbonyl depsipeptides 8c,f and 12d are highly solvent sensitive. These highly fluorescent compounds could be useful for peptide assays. Further photophysical studies of 7-diethylaminocoumarin-labeled depsipeptides 8c,12d within the micellar microenvironment of SDS reflect their ability to bind with the biological membrane, suggesting potential applications in the fields of bio- and medicinal chemistry.

  DOI：

  10.1007/s00726-013-1483-3
• 作为产物：
  描述：

  在 盐酸 作用下， 以 1,4-二氧六环 、 水 为溶剂， 反应 2.08h， 生成 (S)-2-((S)-2-(2-aminoacetoxy)-4-methylpentanamido)-4-(methylthio)butanoic acid hydrochloride
  参考文献：
  名称：

  Photophysics of novel coumarin-labeled depsipeptides in solution: sensing interactions with SDS micelle via TICT model

  摘要：

  N-Acylbenzotriazoles enable the synthesis (69-92 % yield) of blue to green fluorescent coumarin-labeled depsidipeptides 8a-f (quantum yields 0.004-0.97) and depsitripeptides 12a-d (quantum yields 0.02-0.96). Detailed photophysical studies of fluorescent coumarin-labeled depsipeptides 8a-f and 12a-d are reported for both polar protic and polar aprotic solvents. 7-Methoxy and 7-diethylaminocoumarin-3-ylcarbonyl depsipeptides 8c,f and 12d are highly solvent sensitive. These highly fluorescent compounds could be useful for peptide assays. Further photophysical studies of 7-diethylaminocoumarin-labeled depsipeptides 8c,12d within the micellar microenvironment of SDS reflect their ability to bind with the biological membrane, suggesting potential applications in the fields of bio- and medicinal chemistry.

  DOI：

  10.1007/s00726-013-1483-3