Ala-Tyr-Phe | 1620159-33-2

• 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: Ala-Tyr-Phe
• 英文别名: (2S)-2-[[(2S)-2-[[(2S)-2-aminopropanoyl]amino]-3-(4-hydroxyphenyl)propanoyl]amino]-3-phenylpropanoic acid
• CAS: 1620159-33-2
• 化学式: C₂₁H₂₅N₃O₅
• 分子量: 399.447
• InChiKey: JNJHNBXBGNJESC-KKXDTOCCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -2.5
• 重原子数：
  29
• 可旋转键数：
  9
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  142
• 氢给体数：
  5
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  Ala-Tyr-Phe 、 在 对甲苯磺酸 、 sodium nitrite 作用下， 以 甲醇 、 水 、 aq. phosphate buffer 为溶剂， 反应 2.5h， 以37%的产率得到(2S)-2-[[(2S)-2-[[(2S)-2-[7-[3-[2-[2-[3-[[4-(benzylamino)-4-oxobutanoyl]amino]propoxy]ethoxy]ethoxy]propylcarbamoyl]-4-oxo-1,2,3-benzotriazin-3-yl]propanoyl]amino]-3-(4-hydroxyphenyl)propanoyl]amino]-3-phenylpropanoic acid
  参考文献：
  名称：

  Amine-Selective Bioconjugation Using Arene Diazonium Salts

  摘要：

  A novel bioconjugation strategy is presented that relies on the coupling of diazonium terephthalates with amines in proteins. The diazonium captures the amine while the vicinal ester locks it through cyclization, ensuring no reversibility. The reaction is highly efficient and proceeds under mild conditions and short reaction times. Densely functionalized, complex natural products were directly coupled to proteins using low concentrations of coupling partners.

  DOI：

  10.1021/ol5016509

文献信息

• Amine-Selective Bioconjugation Using Arene Diazonium Salts
  作者：Stefan Diethelm、Michael A. Schafroth、Erick M. Carreira

  DOI：10.1021/ol5016509

  日期：2014.8.1

  A novel bioconjugation strategy is presented that relies on the coupling of diazonium terephthalates with amines in proteins. The diazonium captures the amine while the vicinal ester locks it through cyclization, ensuring no reversibility. The reaction is highly efficient and proceeds under mild conditions and short reaction times. Densely functionalized, complex natural products were directly coupled to proteins using low concentrations of coupling partners.