Effective biosynthesis of ethyl (R)-4-chloro-3-hydroxybutanoate by supplementation of l-glutamine, d-xylose and β-cyclodextrin in n-butyl acetate-water media

Journal of Biotechnology

Volumn 203, Issue , 2015, Pages 62-67

  He, Yu Cai ^a   Tao, Zhi Cheng ^a   Ding, Yun ^a   Zhang, Dan Ping ^a   Wu, Yin Qin ^a   Lu, Yun ^a   Liu, Feng ^a   Xue, Yu Feng ^a   Wang, Cheng ^a   Xu, Jian He ^b  

^a CHANGZHOU UNIVERSITY   (China)

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

Author keywords

D Xylose; Ethyl (R) 4 chloro 3 hydroxybutanoate; Ethyl 4 chloro 3 oxobutanoate; L Glutamine; Cyclodextrin, E. coli CCZU A13

Indexed keywords

AMINO ACIDS; BIOCHEMISTRY; BIOSYNTHESIS; CYCLODEXTRINS; ESCHERICHIA COLI; SYNTHESIS (CHEMICAL); VOLATILE FATTY ACIDS;

D-XYLOSE; E. COLI; ETHYL (R)-4-CHLORO-3-HYDROXYBUTANOATE; ETHYL 4-CHLORO-3-OXOBUTANOATE; L-GLUTAMINE;

XYLOSE;

ACETIC ACID BUTYL ESTER; ACETIC ACID ESTER; BETA CYCLODEXTRIN; BUTYRIC ACID DERIVATIVE; ETHYL 4 CHLORO 3 HYDROXYBUTANOATE; ETHYL 4 CHLORO 3 OXOBUTANOATE; GLUTAMINE; OXIDOREDUCTASE; REDUCED NICOTINAMIDE ADENINE DINUCLEOTIDE; UNCLASSIFIED DRUG; WATER; XYLOSE; ACETIC ACID DERIVATIVE; ACETOACETIC ACID DERIVATIVE; BACTERIAL PROTEIN; BETA CYCLODEXTRIN DERIVATIVE; BUTYL ACETATE; CULTURE MEDIUM; ETHYL 4-CHLORO-3-HYDROXYBUTANOATE; ETHYL 4-CHLORO-3-OXOBUTANOATE;

ARTICLE; ASYMMETRIC SYNTHESIS; BACTERIAL CELL; BIOSYNTHESIS; BIOTRANSFORMATION; COMPLEX FORMATION; CONTROLLED STUDY; ENZYME ACTIVITY; ESCHERICHIA COLI; INFRARED SPECTROSCOPY; NONHUMAN; PRIORITY JOURNAL; REDUCTION; SCANNING ELECTRON MICROSCOPY; TRANSMISSION ELECTRON MICROSCOPY; ULTRAVIOLET SPECTROSCOPY; CULTURE MEDIUM; GENETICS; METABOLISM;

ACETATES; ACETOACETATES; BACTERIAL PROTEINS; BETA-CYCLODEXTRINS; BUTYRATES; CULTURE MEDIA; ESCHERICHIA COLI; GLUTAMINE; OXIDOREDUCTASES; WATER; XYLOSE;

EID: 84927933605     PISSN: 01681656     EISSN: 18734863     Source Type: Journal    
DOI: 10.1016/j.jbiotec.2015.03.011     Document Type: Article

References (28)

1. Breuer M., Ditrich K., Habicher T., Hauer B., Kesseler M., Sturmer R., Zelinski T. Industrial methods for the production of optically active intermediates. Angew. Chem. Int. Ed. Engl. 2004, 43:788-824.
2. Ema T., Ide S., Okita N., Sakai T. Highly efficient chemoenzymatic synthesis of methyl (R)-o-chloromandelate, a key intermediate for clopidogrel, via asymmetric reduction with recombinant Escherichia coli. Adv. Synth. Catal. 2008, 350:2039-2044.
3. Ema T., Yagasaki H., Okita N., Takeda M., Sakai T. Asymmetric reduction of ketones using recombinant E. coli cells that produce a versatile carbonyl reductase with high enantioselectivity and broad substrate specificity. Tetrahedron 2006, 62:6143-6149.
4. He Y.C., Liu F., Gong L., Lu T., Ding Y., Zhang D.P., Qing Q., Zhang Y. Improving enzymatic hydrolysis of corn stover pretreated by ethylene glycol-perchloric acid-water mixture. Appl. Biochem. Biotechnol. 2015, 175:1306-1317.
5. He Y.C., Tao Z.C., Zhang X., Yang Z.X., Xu J.H. Highly efficient synthesis of ethyl (S)-4-chloro-3-hydroxybutanoate and its derivatives by a robust NADH-dependent reductase from E. coli CCZU-K14. Bioresour. Technol. 2014, 161:461-464.
6. He Y.C., Yang Z.X., Zhang D.P., Tao Z.C., Chen C., Chen Y.T., Guo F., Xu J.H., Huang L., Chen R.J., Ma X.F. Biosynthesis of ethyl (S)-4-chloro-3-hydroxybutanoate by NADH-dependent reductase from E. coli CCZU-Y10 discovered by genome data mining using mannitol as cosubstrate. Appl. Biochem. Biotechnol. 2014, 173:2042-2053.
7. He Y.C., Zhang D.P., Tao Z.C., Zhang X., Yang Z.X. Discovery of a reductase-producing strain recombinant E. coli CCZU-A13 using colorimetric screening and its whole cell-catalyzed biosynthesis of ethyl (R)-4-chloro-3-hydroxybutanoate. Bioresour. Technol. 2014, 172:342-348.
8. He Y.C., Zhang Z.J., Xu J.H., Liu Y.Y. Biocatalytic synthesis of R)-(-)-mandelic acid from racemic mandelonitrile by cetyltrimethylammonium bromide-permeabilized cells of Alcaligenes faecalis ECU0401. J. Ind. Microbiol. Biotechnol. 2010, 37:741-750.
9. Houng J.Y., Hsu H.F., Liu Y.H., Wu J.Y. Applying the Taguchi robust design to the optimization of the asymmetric reduction of ethyl 4-chloro acetoacetate by bakers' yeast. J. Biotechnol. 2003, 100:239-250.
10. Hummel W., Gröger H. Strategies for regeneration of nicotinamide coenzymes emphasizing self-sufficient closed-loop recycling systems. J. Biotechnol. 2014, 191:22-31.
11. 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.
12. Li N., Zhang Y.Y., Ye Q., Zhang Y.Z., Chen Y., Chen X.C., Wu J.L., Bai J.X., Xie J.J., Ying H.J. Effect of ribose, xylose, aspartic acid, glutamine and nicotinic acid on ethyl (S)-4-chloro-3-hydroxybutanoate synthesis by recombinant Escherichia coli. Bioresour. Technol. 2012, 118:572-575.
13. Li H.P., Zhao M.M., Yu Z.M., Lei H.J., Zhao H.F. Simutaneous determination of adenosine phosphate and coenzyme I in cells of Saccharomyces cerevisiae by RP-HPLC. J. Food Sci. Biotechnol. (In Chinese) 2012, 31:192-199.
14. Liu X., Chen R., Yang Z.W., Wang J.L., Lin J.P., Wei D.Z. Characterization of a putative stereoselective oxidoreductase from Gluconobacter oxydans and its application in producing ethyl (R)-4-chloro-3-hydroxybutanoate ester. Mol. Biotechnol. 2014, 56:285-295.
15. Liu L.M., Li Y., Shi Z.P., Du G.C., Chen J. Enhancement of pyruvate productivity in Torulopsis glabrata: increase of NAD+ availability. J. Biotechnol. 2006, 126:173-185.
16. Lucas-Abellan C., Fortea M.I., Gabaldon J.A., Nunez-Delicado E. Complexation of resveratrol by native and modified cyclodextrins: determination of complexation constant by enzymatic, solubility and fluorimetric assays. Food Chem. 2008, 111:262-267.
17. Ma B., Pan S.J., Zupancic M.L., Cormack B.P. Assimilation of NAD+ precursors in Candida glabrata. Mol. Microbiol. 2007, 66:14-25.
18. Manosroi A., Saowakhon S., Manosroi J. Enhancement of androstadienedione production from progesterone by biotransformation using the hydroxypropyl-β-cyclodextrin complexation technique. J. Steroid. Biochem. Mol. Biol. 2008, 108:132-136.
19. Mosinger J., Tomankova V., Nemcova I., Zyka J. Cyclodextrins in analytical chemistry. Anal. Lett. 2001, 34:1979-2004.
20. Ni Y., Su Y.N., Li H.D., Zhou J.Y., Sun Z.H. Scalable biocatalytic synthesis of optically pure ethyl (R)-2-hydroxy-4-phenylbutyrate using a recombinant E. coli with high catalyst yield. J. Biotechnol. 2013, 168:493-498.
21. Ni Y., Li C.X., Ma H.M., Zhang J., Xu J.H. Biocatalytic properties of a recombinant aldo-keto reductase with broad substrate spectrum and excellent stereoselectivity. Appl. Microb. Biotechnol. 2010, 89:1111-1118.
22. Ning C.X., Su E.Z., Tian Y.J., Wei D.Z. Combined cross-linked enzyme aggregates (combi-CLEAs) for efficient integration of a ketoreductase and a cofactor regeneration system. J. Biotechnol. 2014, 184:7-10.
23. Nie Y., Xu Y., Hu Q.S., Xiao R. A new strategy to improve the efficiency and sustainability of Candida parapsilosis catalyzing deracemization of (RS)-1-phenyl-1,2-ethanediol under non-growing conditions: increase of NADPH availability. J. Microbiol. Biotechnol. 2009, 19:65-71.
24. Shimizu S., Kataoka M., Morishita A., Katoh M., Morikawa T., Miyoshi T., Yamada H. Microbial asymmetric reduction of ethyl 4-chloro-3-oxobutanoate to optically active ethyl 4-chloro-3-hydroxybutanoate. Biotechnol. Lett. 1990, 12:593-596.
25. 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.
26. Xie Y., Xu J.H., Xu Y. Isolation of a Bacillus strain producing ketone reductase with high substrate tolerance. Bioresour. Technol. 2010, 101:1054-1059.
27. Zhang Q.F., Nie H.C., Shangguan X.C., Yin Z.P., Zheng G.D., Chen J.G. Aqueous solubility and stability enhancement of astilbin through complexation with cyclodextrins. J. Agric. Food Chem. 2013, 61:151-156.
28. Zidovetzki R., Levitan I. Use of cyclodextrins tomanipulate plasma membrane cholesterol content: evidence, misconceptions and control strategies. BBA-Biomembranes 2007, 1768:1311-1324.