2-bromopropionyl-L-glutamine

• 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: 2-bromopropionyl-L-glutamine
• 英文别名: (2S)-5-amino-2-[[(2R)-2-bromopropanoyl]amino]-5-oxopentanoic acid
• 化学式: C₈H₁₃BrN₂O₄
• 分子量: 281.106
• InChiKey: XFLSYHUECOOYGL-UHNVWZDZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.4
• 重原子数：
  15
• 可旋转键数：
  6
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  110
• 氢给体数：
  3
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-bromopropionyl-L-glutamine 在 ammonium hydroxide 作用下， 反应 8.0h， 以99.8%的产率得到L-丙氨酰-L-谷氨酰胺
  参考文献：
  名称：

  Process Research and Development of l-Alanyl-l-glutamine, a Component of Parenteral Nutrition

  摘要：

  A large-scale manufacturing method of L-alanyl-L-glutamine used for a component of parenteral nutrition has been studied. The method consisted of a reaction of D-2-chloro- or D-2-bromopropionic acid with thionyl chloride and Schotten-Baumann reaction with L-glutamine followed by ammonolysis reaction. The intermediate D-2-chloropropionyl-L-glutamine was found to be more stable than its bromo analogue. In the ammonolysis reaction, the former intermediate needed a higher reaction temperature, but the by-products produced had little effect on the quality of the final product, The structures of the by-products were conjectured mainly by mass spectrometry and they were removed by anion resin treatment and recrystallization.

  DOI：

  10.1021/op990079w
• 作为产物：
  描述：

  (R)-2-bromopropionyl chloride 、 L-谷氨酰胺 以 水 、 甲苯 为溶剂， 以72.4%的产率得到2-bromopropionyl-L-glutamine
  参考文献：
  名称：

  Process Research and Development of l-Alanyl-l-glutamine, a Component of Parenteral Nutrition

  摘要：

  A large-scale manufacturing method of L-alanyl-L-glutamine used for a component of parenteral nutrition has been studied. The method consisted of a reaction of D-2-chloro- or D-2-bromopropionic acid with thionyl chloride and Schotten-Baumann reaction with L-glutamine followed by ammonolysis reaction. The intermediate D-2-chloropropionyl-L-glutamine was found to be more stable than its bromo analogue. In the ammonolysis reaction, the former intermediate needed a higher reaction temperature, but the by-products produced had little effect on the quality of the final product, The structures of the by-products were conjectured mainly by mass spectrometry and they were removed by anion resin treatment and recrystallization.

  DOI：

  10.1021/op990079w

文献信息

• Process Research and Development of <scp>l</scp>-Alanyl-<scp>l</scp>-glutamine, a Component of Parenteral Nutrition
  作者：Takahiro Sano、Toru Sugaya、Kunimi Inoue、Sho-ichi Mizutaki、Yasuyuki Ono、Masaji Kasai

  DOI：10.1021/op990079w

  日期：2000.5.1

  A large-scale manufacturing method of L-alanyl-L-glutamine used for a component of parenteral nutrition has been studied. The method consisted of a reaction of D-2-chloro- or D-2-bromopropionic acid with thionyl chloride and Schotten-Baumann reaction with L-glutamine followed by ammonolysis reaction. The intermediate D-2-chloropropionyl-L-glutamine was found to be more stable than its bromo analogue. In the ammonolysis reaction, the former intermediate needed a higher reaction temperature, but the by-products produced had little effect on the quality of the final product, The structures of the by-products were conjectured mainly by mass spectrometry and they were removed by anion resin treatment and recrystallization.