(2R)-2-[[(2R)-2-benzamidopropanoyl]amino]propanoic acid | 165194-89-8

• 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: (2R)-2-[[(2R)-2-benzamidopropanoyl]amino]propanoic acid
• CAS: 165194-89-8
• 化学式: C₁₃H₁₆N₂O₄
• 分子量: 264.281
• InChiKey: IOKQHWCEKSZZKP-RKDXNWHRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  19
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  95.5
• 氢给体数：
  3
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  (R)-tert-butyl 2-(2-benzamidopropanoylthio)acetate 在 R₃₉ from Actinomadura (class C) 、 三氟乙酸 、 sodium chloride 作用下， 以 aq. phosphate buffer 、 水 为溶剂， 反应 2.0h， 生成 (2R)-2-[[(2R)-2-benzamidopropanoyl]amino]propanoic acid
  参考文献：
  名称：

  Synthesis of an enantiopure thioester as key substrate for screening the sensitivity of penicillin binding proteins to inhibitors

  摘要：

  The synthesis of the enantiopure thioester (R)-2-(2-benzamidopropanoylthio) acetic acid was developed. After the exploration of several activation methods, reaction conditions were found for the formation of the thioester bond in the presence of propylphosphonic anhydride with high enantioselectivity (ee > 99%). The thioester activity of Penicillin Binding Proteins is helpful in research programs looking for new lead structures to overcome the problem of bacterial resistance.

  DOI：

  10.3998/ark.5550190.p009.621

文献信息

• Gante, Joachim; Kalthof, Ulrike; Klaerner, Frank-Gerrit, Angewandte Chemie, 1990, vol. 102, # 9, p. 1081 - 1082
  作者：Gante, Joachim、Kalthof, Ulrike、Klaerner, Frank-Gerrit、Weber, Thomas

  DOI：——

  日期：——
• Synthesis of an enantiopure thioester as key substrate for screening the sensitivity of penicillin binding proteins to inhibitors
  作者：Justine F. Simon、André Bouillez、Jean-Marie Frère、André Luxen、Astrid Zervosen

  DOI：10.3998/ark.5550190.p009.621

  日期：——

  The synthesis of the enantiopure thioester (R)-2-(2-benzamidopropanoylthio) acetic acid was developed. After the exploration of several activation methods, reaction conditions were found for the formation of the thioester bond in the presence of propylphosphonic anhydride with high enantioselectivity (ee > 99%). The thioester activity of Penicillin Binding Proteins is helpful in research programs looking for new lead structures to overcome the problem of bacterial resistance.