4-phenylazobenzoyl-L-leucine | 378785-12-7

• 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: 4-phenylazobenzoyl-L-leucine
• 英文别名: (2S)-4-methyl-2-[(4-phenyldiazenylbenzoyl)amino]pentanoic acid
• CAS: 378785-12-7
• 化学式: C₁₉H₂₁N₃O₃
• 分子量: 339.394
• InChiKey: BZBOAVOCLLWKES-KRWDZBQOSA-N

物化性质

• 熔点：
  120.0-122.0 °C(Solv: dichloromethane (75-09-2); hexane (110-54-3))
• 沸点：
  569.3±35.0 °C(Predicted)
• 密度：
  1.18±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  25
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  91.1
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  4-phenylazobenzoyl-L-leucine 在 2,2,6,6-tetramethyl-piperidine-N-oxyl 、 碳酸氢钠 、 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 、 potassium bromide 作用下， 以 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 16.0h， 生成 methyl (3S)-3-[[(2S)-4-methyl-2-[(4-phenyldiazenylbenzoyl)amino]pentanoyl]amino]-2-oxo-4-phenylbutanoate
  参考文献：
  名称：

  α-Ketoester-based photobiological switches: synthesis, peptide chain extension and assay against α-chymotrypsin

  摘要：

  The design, synthesis, photoisomerism and biological testing of two peptide-based photoswitchable inhibitors of a-chymotrypsin are presented. The use of a dipeptide recognition sequence gave a 'slow-tight binding' inhibitor, while the introduction of a carbamate linker to the azobenzene gave a modest enhancement in photoswitching of enzyme activity for the photostationary state enriched in the (Z)-isomer over the (E)-isomer. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(01)00464-4
• 作为产物：
  描述：

  N-(4-phenylazo-benzoyl)-L-leucine methyl ester 在 lithium hydroxide 作用下， 以 甲醇 为溶剂， 反应 0.5h， 以100%的产率得到4-phenylazobenzoyl-L-leucine
  参考文献：
  名称：

  α-Ketoester-based photobiological switches: synthesis, peptide chain extension and assay against α-chymotrypsin

  摘要：

  The design, synthesis, photoisomerism and biological testing of two peptide-based photoswitchable inhibitors of a-chymotrypsin are presented. The use of a dipeptide recognition sequence gave a 'slow-tight binding' inhibitor, while the introduction of a carbamate linker to the azobenzene gave a modest enhancement in photoswitching of enzyme activity for the photostationary state enriched in the (Z)-isomer over the (E)-isomer. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(01)00464-4

文献信息

• Convenient preparations of azo-dye labeled amino acids and amines
  作者：Alan Roy Katritzky、Qi-Yin Chen、Srinivasa Rao Tala

  DOI：10.1039/b802846j

  日期：——

  N-(4-Arylazobenzoyl)-1H-benzotriazoles 3 react with amino acids 4 and amines 6 to give azo-dye labeled amino acids (5a-m) and amines (7a-n) in high yields (74-100%) with retention of chirality.

  N-（4-芳基偶氮苯甲酰基）-1H-苯并三唑3与氨基酸4和胺6反应以高收率（74-100％）得到偶氮染料标记的氨基酸（5a-m）和胺（7a-n）保留手性。
• α-Ketoester-based photobiological switches: synthesis, peptide chain extension and assay against α-chymotrypsin
  作者：Andrew J Harvey、Andrew D Abell

  DOI：10.1016/s0960-894x(01)00464-4

  日期：2001.9

  The design, synthesis, photoisomerism and biological testing of two peptide-based photoswitchable inhibitors of a-chymotrypsin are presented. The use of a dipeptide recognition sequence gave a 'slow-tight binding' inhibitor, while the introduction of a carbamate linker to the azobenzene gave a modest enhancement in photoswitching of enzyme activity for the photostationary state enriched in the (Z)-isomer over the (E)-isomer. (C) 2001 Elsevier Science Ltd. All rights reserved.