Enantioselective cascade biocatalysis for deracemization of 2-hydroxy acids using a three-enzyme system

Microbial Cell Factories

Volumn 15, Issue 1, 2016, Pages

  Xue, Ya Ping ^a   Zeng, Hao ^a   Jin, Xiao Lu ^b   Liu, Zhi Qiang ^a   Zheng, Yu Guo ^a  

^a ZHEJIANG UNIVERSITY OF TECHNOLOGY   (China)

^b Yosemade Pharmaceutical Co Ltd   (China)

Author keywords

2 hydoxy acids; Cascade biocatalysis; Coexpression; Deracemization

Indexed keywords

2 HYDROXYACID; 2 HYDROXYACID DEHYDROGENASE; 2 OXOACID DEHYDROGENASE; ENZYME; GLUCOSE DEHYDROGENASE; OXIDOREDUCTASE; UNCLASSIFIED DRUG;

ARTICLE; BACTERIAL STRAIN; BIOCATALYSIS; BIOCATALYST; BIOTRANSFORMATION; CHEMICAL REACTION; DERACEMIZATION; ENANTIOMER; ENANTIOSELECTIVITY; ENZYME ACTIVITY; ESCHERICHIA COLI; GENETIC RECOMBINATION; NONHUMAN; NUCLEOTIDE SEQUENCE; OXIDATION REDUCTION REACTION; PROCESS DEVELOPMENT; PROTEIN EXPRESSION; RACEMIC MIXTURE;

EID: 84995655518     PISSN: None     EISSN: 14752859     Source Type: Journal    
DOI: 10.1186/s12934-016-0560-1     Document Type: Article

References (41)

1. Gröger H. Enzymatic routes to enantiomerically pure aromatic α-hydroxy carboxylic acids: a further example for the diversity of biocatalysis. Adv Synth Catal. 2001;343:547-58.
2. Tang KW, Yi JM, Huang KL, Zhang GL. Biphasic recognition chiral extraction: a novel method for separation of mandelic acid enantiomers. Chirality. 2009;21:390-5.
3. 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;350:2039-44.
4. Bai YL, Yang ST. Biotransformation of R-2-hydroxy-4-phenylbutyric acid by d-lactate dehydrogenase and Candida boidinii cells containing formate dehydrogenase coimmobilized in a fibrous bed bioreactor. Biotechnol Bioeng. 2005;92:137-46.
5. Urban FJ, Moore BS. Synthesis of optically-active 2-benzyldihydrobenzopyrans for the hypoglycemic agent englitazone. J Heterocycl Chem. 1992;29:431-8.
6. Chen X, Wu QQ, Zhu DM. Enzymatic synthesis of chiral 2-hydroxy carboxylic acids. Process Biochem. 2015;50:759-70.
7. Gruber CC, Lavandera I, Faber K, Kroutil W. From a racemate to a single enantiomer: deracemization by stereoinversion. Adv Synth Catal. 2006;348:1789-805.
8. Ricca E, Brucher B, Schrittwieser JH. Multi-Enzymatic cascade reactions: overview and perspectives. Adv Synth Catal. 2011;353:2239-62.
9. Guo JL, Mu XQ, Zheng CG, Xu Y. A highly stable whole-cell biocatalyst for the enantioselective synthesis of optically active alpha-hydroxy acids. J Chem Technol Biotechnol. 2009;84:1787-92.
10. Gao C, Qiu JH, Li JC, Ma CQ, Tang HZ, Xu P. Enantioselective oxidation of racemic lactic acid to d-lactic acid and pyruvic acid by Pseudomonas stutzeri SDM. Bioresour Technol. 2009;100:1878-80.
11. van Hellemond EW, Vermote L, Koolen W, Sonke T, Zandvoort E, Heuts D, Janssen DB, Fraaije MW. Exploring the biocatalytic scope of alditol oxidase from streptomyces coelicolor. Adv Synth Catal. 2009;351:1523-30.
12. Campbell RF, Fitzpatrick K, Inghardt T, Karlsson O, Nilsson K, Reilly JE, Yet L. Enzymatic resolution of substituted mandelic acids. Tetrahedron Lett. 2003;44:5477-81.
13. Kumar S, Mohan U, Kamble AL, Pawar S, Banerjee UC. Cross-linked enzyme aggregates of recombinant Pseudomonas putida nitrilase for enantioselective nitrile hydrolysis. Bioresour Technol. 2010;101:6856-8.
14. Yamamoto K, Oishi K, Fujimatsu I, Komatsu KI. Production of R-(-)-mandelic acid from mandelonitrile by Alcaligenes faecalis ATCC 8750. Appl Environ Microbiol. 1991;57:3028-32.
15. Sosedov O, Matzer K, Burger S, Kiziak C, Baum S, Altenbuchner J, Chmura A, van Rantwijk F, Stolz A. Construction of recombinant Escherichia coli catalysts which simultaneously express an (S)-oxynitrilase and different nitrilase variants for the synthesis of (S)-mandelic acid and (S)-mandelic amide from benzaldehyde and cyanide. Adv Synth Catal. 2009;351:1531-8.
16. Wang YS, Cheng F, Zheng RC, Wang YJ, Zheng YG. Characterization of an enantioselective amidase with potential application to asymmetric hydrolysis of (R, S)-2, 2-dimethylcyclopropane carboxamide. World J Microbiol Biotechnol. 2011;27:2885-92.
17. Gourinchas G, Busto E, Killinger M, Richter N, Wiltschi B, Kroutil W. A synthetic biology approach for the transformation of L-α-amino acids to the corresponding enantiopure (R)- or (S)-α-hydroxy acids. Chem Commun. 2015;51:2828-31.
18. Xue YP, Zheng YG, Zhang YQ, Sun JL, Liu ZQ, Shen YC. One-pot, single-step deracemization of 2-hydroxyacids by tandem biocatalytic oxidation and reduction. Chem Commun. 2013;49:10706-8.
19. Schrittwieser JH, Sattler J, Resch V, Mutti FG, Kroutil W. Recent biocatalytic oxidation-reduction cascades. Curr Opin Biotechnol. 2011;15:249-56.
20. Chen X. Sequential one-pot multienzyme (OPME) systems for the synthesis of carbohydrates and glycoconjugates. Glycobiology. 2015;25:1291.
21. Classen T, Korpak M, Schölzel M, Pietruszka J. Stereoselective enzyme cascades: an efficient synthesis of chiral γ-butyrolactones. ACS Catal. 2014;4:1321-31.
22. Liu J, Li Z. Cascade biotransformations via enantioselective reduction, oxidation, and hydrolysis: preparation of (R)-δ-lactones from 2-alkylidenecyclopentanones. ACS Catal. 2013;3:908-11.
23. Sattler JH, Fuchs M, Tauber K, Mutti FG, Faber PK, Pfeffer J, Haas T, Kroutil PW. Redox self-sufficient biocatalyst network for the amination of primary alcohols. Angew Chem Int Ed. 2012;124:9290-3.
24. Xue R, Woodley JM. Process technology for multi-enzymatic reaction systems. Bioresour Technol. 2012;115:183-95.
25. Lopez-Gallego F, Schmidt-Dannert C. Multi-enzymatic synthesis. Curr Opin Chem Biol. 2010;14:174-83.
26. Voss CV, Gruber CC, Kroutil W. Deracemization of secondary alcohols through a concurrent tandem biocatalytic oxidation and reduction. Angew Chem Int Ed. 2008;47:741-5.
27. Li YL, Xu JH, Xu Y. Deracemization of aryl secondary alcohols via enantioselective oxidation and stereoselective reduction with tandem whole-cell biocatalysts. J Mol Catal B Enzym. 2010;64:48-52.
28. Songür R, Atici EM, Mehmetoğlu Ü. Deracemization of 1-phenyl ethanol via tandem biocatalytic oxidation and reduction. Curr Opin Biotechnol. 2011;22(Supplement 1):S56-7.
29. Kato DI, Miyamoto K, Ohta H. Preparation of optically active 4-chlorophenylalanine from its racemate by deracemization technique using transformant Escherichia coli cells. Biocatal Biotransform. 2005;23:375-9.
30. Caligiuri A, D'Arrigo P, Gefflaut T, Molla G, Pollegioni L, Rosini E, Rossi C, Servi S. Multistep enzyme catalysed deracemisation of 2-naphthyl alanine. Biocatal Biotransform. 2006;24:409-13.
31. Mutti FG, Knaus T, Scrutton NS, Breuer M, Turner NJ. Conversion of alcohols to enantiopure amines through dual-enzyme hydrogen-borrowing cascades. Science. 2015;349:1525-9.
32. Zhang J, Wu S, Wu J, Li Z. Enantioselective cascade biocatalysis via epoxide hydrolysis and alcohol oxidation: one-pot synthesis of (R)-α-hydroxy ketones from meso- or racemic epoxides. ACS Catal. 2015;5:51-8.
33. Fan CW, Xu GC, Ma BD, Bai YP, Zhang J, Xu JH. A novel d-mandelate dehydrogenase used in three-enzyme cascade reaction for highly efficient synthesis of non-natural chiral amino acids. J Biotechnol. 2015;195:67-71.
34. Resch V, Fabian WMF, Kroutil W. Deracemisation of mandelic acid to optically pure non-natural l-phenylglycine via a redox-neutral biocatalytic cascade. Adv Synth Catal. 2010;352:993-7.
35. Xue YP, Wang W, Wang YJ, Liu ZQ, Zheng YG, Shen YC. Isolation of enantioselective alpha-hydroxyacid dehydrogenases based on a high-throughput screening method. Bioprocess Biosyst Eng. 2012;35:1515-22.
36. Xue YP, Tian FF, Ruan LT, Liu ZQ, Zheng YG, Shen YC. Concurrent obtaining of aromatic (R)-2-hydroxyacids and aromatic 2-ketoacids by asymmetric oxidation with a newly isolated Pseudomonas aeruginosa ZJB1125. J Biotechnol. 2013;167:271-8.
37. Dewanti AR, Xu Y, Mitra B. Role of glycine 81 in (S)-mandelate dehydrogenase from Pseudomonas putida in substrate specificity and oxidase activity. Biochemistry. 2004;43:10692-700.
38. Dewanti AR, Mitra B. A transient intermediate in the reaction catalyzed by (S)-mandelate dehydrogenase from Pseudomonas putida. Biochemistry. 2003;42:12893-901.
39. Rydzanicz R, Zhao XS, Johnson PE. Assembly PCR oligo maker: a tool for designing oligodeoxynucleotides for constructing long DNA molecules for RNA production. Nucleic Acids Res. 2005;33:W521-5.
40. Streitenberger SA, Lopez-Mas JA, Sanchez-Ferrer A, Garcia-Carmona F. A study on the kinetic mechanism of apoenzyme reconstitution from Aerococcus viridans lactate oxidase. J Enzym Inhib Med Chem. 2003;18:285-8.
41. Chen CS, Fujimoto Y, Girdaukas G, Sih CJ. Quantitative analyses of biochemical kinetic resolutions of enantiomers. J Am Chem Soc. 1982;104:7294-9.