Chin. J. Org. Chem. ›› 2006, Vol. 26 ›› Issue (04): 514-517. Previous Articles     Next Articles

Original Articles

D-谷氨酰胺的制备

钱绍松,吴晓燕,李加友,刘毅,陈然,焦庆才*   

  1. (南京大学生命科学院医药生物技术国家重点实验室 南京 210093)
  • 收稿日期:2005-06-14 修回日期:2005-10-31 发布日期:2006-03-31
  • 通讯作者: 焦庆才

Preparation of D-Glutamine from Glutamic Acid

QIAN Shao-Song,WU Xiao-Yan,LI Jia-You,LIU Yi
CHEN Ran,JIAO Qing-Cai*   

  1. (State Key Laboratory of Pharmaceutic Biotechnology, School of Life Science, Nanjing University, Nanjing 210093)
  • Received:2005-06-14 Revised:2005-10-31 Published:2006-03-31
  • Contact: JIAO Qing-Cai

Optically pure D-glutamine was prepared by biotransformations of DL-glutamine manufactured by chemical synthesis. Firstly, DL-glutamine was synthesized from DL-glutamic acid on larger scale. Protected DL-glutamic acid was prepared by using inexpensive phthaloyl as protecting group. Then N-phthaloyl-DL-glutamic acid anhydride was synthesized with protected DL-glutamic acid and acetic anhydride under reflux for 15 min. Un-der ambient temperature and normal pressure, N-phthaloyl-DL-glutamine was produced by reacting N-phthaloyl-DL-glutamic acid anhydride with 2 mol/L ammonia solution. After the phthaloyl was removed from the intermediate with 0.5 mol/L hydrazine hydrate under ambient temperature for 48 h DL-glutamine mixture was obtained in 57% yields. L-Glutamine in the racemic mixture was selectively decarboxylated to 4-aminobutanamide by the decarboxylase of E. coli AS1.505. Under the following conditions: temperature of 37 ℃, reaction time of 8 h, pH of 4.8, substrate concentration of 30 g/L, D-glutamine was efficiently produced.

Key words: decarboxylase, DL-glutamic acid, D-glutamine