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珊瑚色诺卡氏菌全细胞催化(RS)-4-氟苯甘氨酸去消旋化为(S)-4-氟苯甘氨酸
引用本文:夏仕文.珊瑚色诺卡氏菌全细胞催化(RS)-4-氟苯甘氨酸去消旋化为(S)-4-氟苯甘氨酸[J].分子催化,2015(4):307-314.
作者姓名:夏仕文
作者单位:重庆邮电大学生物信息学院
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,5mmol/L(R)-4-氟苯甘氨酸和10mmol/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。

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
收稿时间:7/9/2015 12:00:00 AM
修稿时间:2015/8/17 0:00:00

Biocatalytic deracemization of (RS)-4-fluorophenylglycine to (S)-4-fluorophenylglycine by whole cells of Nocardia corallina CGMCC 4.1037
Abstract: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 directions. The effects of reaction conditions on the stereo-inversion of (R)-4-fluorophenylglycine were studied. Under the optimal conditions, 5mmol/L (R)-, and 10mmol/L (RS)-4-fluorophenylglycine were stereo-inverted and deracemized to (S)-4-fluorophenylglycine in 52% 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.
Keywords:Nocardia corallina CGMCC 4  1037  Stereo-inversion  Deracemization  (RS)-4-fluorophenylglycine  (S)-4-fluorophenylglycine
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