(S)-2-(2-benzamidopropanoylthio)acetic acid

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (S)-2-(2-benzamidopropanoylthio)acetic acid
• 英文别名: 2-[(2S)-2-benzamidopropanoyl]sulfanylacetic acid
• 化学式: C₁₂H₁₃NO₄S
• 分子量: 267.306
• InChiKey: OEJDVGZWJKPUDA-QMMMGPOBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  18
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  109
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (S)-2-(2-benzamidopropanoylthio)acetic acid 在 penicillin binding proteins with 5204 from a penicillin sensitive stain of Streptococcus pneumoniae 、 水 、 sodium chloride 作用下， 以 aq. phosphate buffer 为溶剂， 生成 N-苯甲酰-L-丙氨酸 、 巯基乙酸
  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
• 作为产物：
  描述：

  Bz-D-丙氨酸 在 N-甲基吗啉 、 1-丙基磷酸酐 、 三氟乙酸 作用下， 以 水 、 乙酸乙酯 为溶剂， 反应 2.0h， 生成 (S)-2-(2-benzamidopropanoylthio)acetic 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

• 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.