Highly efficient synthesis of ethyl (S)-4-chloro-3-hydroxybutanoate and its derivatives by a robust NADH-dependent reductase from E. coli CCZU-K14

Bioresource Technology

Volumn 161, Issue , 2014, Pages 461-464

  He, Yu Cai ^a,b   Tao, Zhi Cheng ^a   Zhang, Xian ^b   Yang, Zhen Xing ^a   Xu, Jian He ^b  

^a CHANGZHOU UNIVERSITY   (China)

^b EAST CHINA UNIVERSITY OF SCIENCE AND TECHNOLOGY   (China)

Author keywords

Asymmetric reduction; Biotransformation; Ethyl (S) 4 chloro 3 hydroxybutanoate; Ethyl 4 chloro 3 oxobutanoate; Recombinant E. coli CCZU K14

Indexed keywords

ENZYME ACTIVITY; SUBSTRATES;

ASYMMETRIC REDUCTION; BIOTRANSFORMATION; ETHYL (S)-4-CHLORO-3-HYDROXYBUTANOATE; ETHYL 4-CHLORO-3-OXOBUTANOATE; RECOMBINANT E. COLI;

ESCHERICHIA COLI;

ALCOHOL DERIVATIVE; ALIPHATIC COMPOUND; AROMATIC COMPOUND; BUTYRIC ACID DERIVATIVE; CARBONYL REDUCTASE; ETHYL (S) 4 CHLORO 3 HYDROXYBUTANOATE; ETHYL 4 CHLORO 3 OXOBUTANOATE; OXIDOREDUCTASE; REDUCED NICOTINAMIDE ADENINE DINUCLEOTIDE; UNCLASSIFIED DRUG; ALCOHOL DEHYDROGENASE; ETHYL 4-CHLORO-3-HYDROXYBUTANOATE; RECOMBINANT PROTEIN;

ALCOHOL; BACTERIUM; BIOTRANSFORMATION; ENZYME ACTIVITY; GENE EXPRESSION; GENOME; INDUSTRIAL PRODUCTION; RECOMBINATION; SUBSTRATE;

ARTICLE; DRUG SYNTHESIS; DRUG TRANSFORMATION; ENANTIOSELECTIVITY; ENZYME ACTIVITY; ENZYME SPECIFICITY; ESCHERICHIA COLI; ESCHERICHIA COLI CCZU K14; GENE OVEREXPRESSION; GENE SEQUENCE; INDUSTRIAL PRODUCTION; NONHUMAN; PRIORITY JOURNAL; SEQUENCE ANALYSIS; STEREOCHEMISTRY; CANDIDA; ENZYMOLOGY; METABOLISM; SYNTHESIS;

ALCOHOL OXIDOREDUCTASES; BUTYRATES; CANDIDA; ESCHERICHIA COLI; RECOMBINANT PROTEINS; SUBSTRATE SPECIFICITY;

EID: 84899844155     PISSN: 09608524     EISSN: 18732976     Source Type: Journal    
DOI: 10.1016/j.biortech.2014.03.133     Document Type: Article

References (12)

1. Cai P., An M.D., Xu L., Xu S., Hao N., Li Y., Guo K., Yan M. Development of a substrate-coupled biocatalytic process driven by an NADPH-dependent sorbose reductase from Candida albicans for the asymmetric reduction of ethyl 4-chloro-3-oxobutanoate. Biotechnol. Lett. 2012, 34:2223-2227.
2. Cao H., Mi L., Ye Q., Zhang G.L., Yan M., Wang Y., Zhang Y.Y., Li X.M., Xu L., Xiong J., Ouyang P.K., Ying H.J. Purification and characterization of a novel NADH-dependent carbonyl reductase from Pichia stipitis involved in biosynthesis of optically pure ethyl (S)-4-chloro-3-hydroxybutanoate. Bioresour. Technol. 2011, 102:1733-1739.
3. He Y.C., Ma C.L., Yang Z.X., Zhou M., Xing Z., Ma J.T., Yu H.L. Highly enantioselective oxidation of phenylmethyl sulfide and its derivatives into optically pure (S)-sulfoxides with Rhodococcus sp. CCZU10-1 in an n-octane-water biphasic system. Appl. Microbiol. Biotechnol. 2013, 97:10329-10337.
4. He J.Y., Sun Z.H., Ruan W.J., Xu Y. Biocatalytic synthesis of ethyl (S)-4-chloro-3-hydroxy-butanoate in an aqueous-organic solvent biphasic system using Aureobasidium pullulans CGMCC 1244. Process Biochem. 2006, 41:244-249.
5. He Y.C., Zhou Q., Ma C.L., Cai Z.Q., Wang L.Q., Zhao X.Y., Chen Q., Gao D.Z., Zheng M., Wang X.D., Sun Q. Biosynthesis of benzoylformic acid from benzoyl cyanide by a newly isolated Rhodococcus sp. CCZU10-1 in toluene-water biphasic system. Bioresour. Technol. 2012, 115:88-95.
6. Kizaki N., Yasohara Y., Hasegawa J., Wada M., Kataoka M., Shimizu S. Synthesis of optically pure ethyl (S)-4-chloro-3-hydroxybutanoate by Escherichia coli transformant cells coexpressing the carbonyl reductase and glucose dehydrogenase genes. Appl. Microbiol. Biotechnol. 2001, 55:590-595.
7. Wang L.J., Li C.X., Ni Y., Zhang J., Liu X., Xu J.H. Highly efficient synthesis of chiral alcohols with a novel NADH-dependent reductase from Streptomyces coelicolor. Bioresour. Technol. 2011, 102:7023-7028.
8. Yamamoto H., Mitsuhashi K., Kimoto N., Esaki N., Kobayshi Y. A novel NADH-dependent carbonyl reductase from Kluyveromyces aestuarii and comparison of NADH-regeneration system for the synthesis of ethyl (S)-4-chloro-3-hydroxybutanoate. Biosci. Biotechnol. Biochem. 2004, 68:638-649.
9. Yasohara Y., Kizaki N., Hasegawa J., Wada M., Kataoka M., Shimizu S. Molecular cloning and overexpression of gene encoding an NADPH-dependent carbonyl reductase from Candida magnoliae, involved in stereoselective reduction of ethyl 4-choloro-3-oxobutanoate. Biosci. Biotechnol. Biochem. 2000, 64:1430-1436.
10. Ye Q., Cao H., Mi L., Yan M., Wang Y., He Q.T., Li J., Xu L., Chen Y.J., Xiong J., Ouyang P.K., Ying H.J. Biosynthesis of (S)-4-chloro-3-hydroxybutanoate ethyl using Escherichia coli co-expressing a novel NADH-dependent carbonyl reductase and a glucose dehydrogenase. Bioresour. Technol. 2010, 101:8911-8914.
11. Ye Q., Cao H., Yan M., Cao F., Zhang Y.Y., Li X.M., Xu L., Chen Y., Xiong J., Ouyang P.K., Ying H.J. Construction and co-expression of a polycistronic plasmid encoding carbonyl reductase and glucose dehydrogenase for production of ethyl (S)-4-chloro-3-hydroxybutanoate. Bioresour. Technol. 2010, 101:6761-6767.
12. Ye Q., Yan M., Yao Z., Xu L., Cao H., Li Z.J., Chen Y., Li S.Y., Bai J.X., Xiong J., Ying H.J., Ouyang P.K. A new member of the short-chain dehydrogenases/reductases superfamily: purification, characterization and substrate specificity of a recombinant carbonyl reductase from Pichia stipitis. Bioresour. Technol. 2009, 100:6022-6027.