Enzymatic synthesis of L-norephedrine by coupling recombinant pyruvate decarboxylase and ω-transaminase

被引:25
作者
Wu, Xuri [1 ,2 ]
Fei, Mengdan [1 ,2 ]
Chen, Yong [1 ,2 ]
Wang, Zongqiang [1 ,2 ]
Chen, Yijun [1 ,2 ]
机构
[1] China Pharmaceut Univ, State Key Lab Nat Med, Nanjing 210009, Jiangsu, Peoples R China
[2] China Pharmaceut Univ, Biol Chem Lab, Nanjing 210009, Jiangsu, Peoples R China
关键词
L-Norephedrine; L-Phenylacetylcarbinol; Biosynthesis; Pyruvate decarboxylase; omega-Transaminase; VIBRIO-FLUVIALIS [!text type='JS']JS[!/text]17; CHIRAL AMINES; ASYMMETRIC-SYNTHESIS; (R)-PHENYLACETYLCARBINOL PRODUCTION; L-HOMOPHENYLALANINE; KINETIC RESOLUTION; CANDIDA-UTILIS; SUBSTRATE; BIOCATALYSIS; ENANTIOMERS;
D O I
10.1007/s00253-014-5797-1
中图分类号
Q81 [生物工程学(生物技术)]; Q93 [微生物学];
学科分类号
071005 ; 0836 ; 090102 ; 100705 ;
摘要
l-Norephedrine, a natural plant alkaloid, possesses similar activity as ephedrine and can be used as a vicinal amino alcohol for the asymmetric synthesis of a variety of optically pure compounds, including pharmaceuticals, fine chemicals, and agrochemicals. Because of the existence of two asymmetric centers, efficient synthesis of l-norephedrine has been challenging. In the present study, an R-selective pyruvate decarboxylase from Saccharomyces cerevisiae and an S-selective omega-transaminase from Vibrio fluvialis JS17 were coupled to develop a sequential process for the stereoselective biosynthesis of l-norephedrine. After systematic optimization of the reaction conditions, a green, economic, and practical biocatalytic method to prepare l-norephedrine was established to achieve de and ee values of greater than 99.5 % and a molar yield over 60 %. The present coupling approach can facilitate the development of sequential reactions by various biocatalysts.
引用
收藏
页码:7399 / 7408
页数:10
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