Z-Phe-(R)-(α-trifluoromethyl)Ala-OMe | 852715-92-5

• 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: Z-Phe-(R)-(α-trifluoromethyl)Ala-OMe
• 英文别名: Cbz-Phe-aMeAla(F3)-OMe；methyl (2R)-3,3,3-trifluoro-2-methyl-2-[[(2S)-3-phenyl-2-(phenylmethoxycarbonylamino)propanoyl]amino]propanoate
• CAS: 852715-92-5
• 化学式: C₂₂H₂₃F₃N₂O₅
• 分子量: 452.43
• InChiKey: GDUYYZIUTPMVGV-LAUBAEHRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  32
• 可旋转键数：
  10
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  93.7
• 氢给体数：
  2
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  L-丙氨酰胺 、 Z-Phe-(R)-(α-trifluoromethyl)Ala-OMe 在 carboxypeptidase Y sodium chloride 、 calcium chloride 、 4-羟乙基哌嗪乙磺酸 作用下， 以 水 、 二甲基亚砜 为溶剂， 以20%的产率得到Z-Phe-(R)-(α-trifluoromethyl)Ala-Ala-NH2
  参考文献：
  名称：

  Discovery of carboxypeptidase Y as a catalyst for the incorporation of sterically demanding α-fluoroalkyl amino acids into peptides

  摘要：

  The first example of a direct enzymatic coupling of two different, sterically demanding C-alpha-fluoroalkyl amino acids to amino acid nucleophiles is reported. N-Protected Ala methyl ester derivatives bearing a methyl-, difluoromethyl-, or trifluoromethyl group, respectively, instead of the alpha-proton were accepted as substrates by carboxypeptidase Y and could, therefore, be coupled directly to various nucleophiles. (C) 2003 Published by Elsevier Ltd.

  DOI：

  10.1016/j.tetlet.2003.12.007
• 作为产物：
  描述：

  N-苄氧羰基-L-苯丙氨酸 、 2-氨基-2-三氟甲基丙酸甲酯 生成 Z-Phe-(S)-(α-trifluoromethyl)Ala-OMe 、 Z-Phe-(R)-(α-trifluoromethyl)Ala-OMe
  参考文献：
  名称：

  Discovery of carboxypeptidase Y as a catalyst for the incorporation of sterically demanding α-fluoroalkyl amino acids into peptides

  摘要：

  The first example of a direct enzymatic coupling of two different, sterically demanding C-alpha-fluoroalkyl amino acids to amino acid nucleophiles is reported. N-Protected Ala methyl ester derivatives bearing a methyl-, difluoromethyl-, or trifluoromethyl group, respectively, instead of the alpha-proton were accepted as substrates by carboxypeptidase Y and could, therefore, be coupled directly to various nucleophiles. (C) 2003 Published by Elsevier Ltd.

  DOI：

  10.1016/j.tetlet.2003.12.007