期刊文献+

珊瑚色诺卡氏菌CGMCC 4.1037全细胞催化(RS)-4-氟苯甘氨酸去消旋化为(S)-4-氟苯甘氨酸 被引量:3

Biocatalytic Deracemization of( RS)-4-Fluorophenylglycine to( S)-4-Fluorophenylglycine by Whole Cells of Nocardia Corallina CGMCC 4.1037
原文传递
导出
摘要 珊瑚色诺卡氏菌CGMCC 4.1037全细胞能够催化4-氟苯甘氨酸的(R)-对映体立体反转为(S)-对映体,相反方向的反应不能发生.研究了反应条件对(R)-4-氟苯甘氨酸立体反转的影响.在最优反应条件下,5 mmol/L(R)-4-氟苯甘氨酸和10 mmol/L(RS)-4-氟苯甘氨酸分别立体反转和去消旋化为(S)-4-氟苯甘氨酸,产率为52%和63%,ee为99.5%和99.2%.(RS)-4-氟苯甘氨酸的去消旋化过程是通过珊瑚色诺卡氏菌CGMCC 4.1037全细胞中的两个酶催化反应实现的.(R)-氨基酸氧化酶催化(R)-4-氟苯甘氨酸氧化脱氨形成4-氟苯甲酰甲酸,(S)-氨基酸转移酶催化4-氟苯甲酰甲酸转氨化为(S)-4-氟苯甘氨酸.讨论了4-氟苯甘氨酸两个对映体的代谢途径. Whole cells of Nocardia corallina CGMCC 4.1037 were capable of catalyzing the stereo-inversion of( R)-4-fluorophenylglycine to its( S)-enantiomer,but not in the reverse direction. The effects of reaction conditions on the stereo-inversion of( R)-4-fluorophenylglycine were studied. Under the optimal conditions,5mmol / L( R)-,and 10 mmol / L( RS)-4-fluorophenylglycine were stereo-inverted and deracemized to( S)-4-fluorophenylglycine in52% and 63% yield,99. 5% and 99. 2 % ee respectively. The deracemization process of( RS)-4-fluorophenylglycine was realized by two enzymatic reactions in the whole cells of Nocardia corallina CGMCC 4.1037.( R)-4-fluorophenylglycine is oxidized to 4-fluorobenzoylformic acid by( R)-amino acid oxidase,and 4-fluorobenzoylformic acid is converted to( S)-4-fluorophenylglycine by( S)-amino acid transferase. The metabolic pathways of both enantiomers of 4-fluorophenylglycin were also discussed.
出处 《分子催化》 EI CAS CSCD 北大核心 2015年第4期307-314,共8页 Journal of Molecular Catalysis(China)
基金 重庆市科技攻关计划项目(CSTC2009AC5088) 重庆市"企业科技特派员-百人计划行动"项目(CSTC2009DA-B21)
关键词 珊瑚色诺卡氏菌CGMCC 4.1037 立体反转 去消旋化 (RS)-4-氟苯甘氨酸 (S)-4-氟苯甘氨酸 Nocardia corallina CGMCC 4.1037 stereo-inversion deracemization (RS)-4-fluorophenylglycine (S)-4-fluorophenylglycine
  • 相关文献

参考文献22

二级参考文献49

  • 1Michael.美国新生代[J].网球大师,2013,0(9):32-35. 被引量:6
  • 2彭阳峰,何佺,王家荣,高浩其,蔡水洪,田禾.通过形成二酪氨酸酯酒石酸盐法制备D-酪氨酸的新方法[J].有机化学,2006,26(1):69-76. 被引量:6
  • 3辛艳飞,周向军,王永祥.D型氨基酸氧化酶活性对于D-硝基精氨酸手性转化的影响[J].生物化学与生物物理进展,2006,33(2):135-139. 被引量:2
  • 4Breuer M,Ditrich K,Habicher T,et al.Industrial meth-ods for the production of optically active intermediates[J].Angew.Chem.Int.Ed.,2004,43:788-824.
  • 5Miyazawa T.Enzymatic resolutionof amino acids[J].Amino.Acid.,1999,16:191-213.
  • 6Huh J W,Yokoigawa K,Esaki,et al.Synthesis of L-proline from the racemate by coupling of enzymatic enan-tiospecific oxidation and chemical non-enantiospecific re-duction[J].L.Fermet.Bioeng.,1992,74:189-190.
  • 7Soda K,Oikawa T,Yokoigawa K.One-pot chemo-enzy-matic enantiomerization of racemates[J].J.Mol.Catal.B:Enzymatic,2001,11:149-153.
  • 8Beard T M,Turner N J.Deracemisation and stereoinver-sion of alpha-amino acids using D-amino acid oxidase andhydride reducing agents[J].Chem.Commun.,2002,246-247.
  • 9Fotheringham I G,Archer R,Carr R,et al.Preparationderacemization of unnatural amino acids[J].Biochem.Soc.Trans.,2006,34:287-290.
  • 10Gabler M,Hensel M,Fischer L.Detection and substrateselectivity of new microbial D amino acid oxidases[J].Enzyme and Microb Technol,2000,27:605-611.

共引文献15

同被引文献124

引证文献3

二级引证文献9

相关作者

内容加载中请稍等...

相关机构

内容加载中请稍等...

相关主题

内容加载中请稍等...

浏览历史

内容加载中请稍等...
;
使用帮助 返回顶部