A NADH-accepting imine reductase variant: Immobilization and cofactor regeneration by oxidative deamination

Journal of Biotechnology

Volumn 230, Issue , 2016, Pages 11-18

  Gand, Martin ^a   Thöle, Christian ^a   Müller, Hubertus ^a   Brundiek, Henrike ^a   Bashiri, Ghader ^b   Höhne, Matthias ^a  

^a UNIVERSITY OF GREIFSWALD   (Germany)

^b UNIVERSITY OF AUCKLAND   (New Zealand)

Author keywords

Cofactor specificity; Coupled oxidative deamination; Imine reductase; Immobilization; Preparative scale biocatalysis; Rational design

Indexed keywords

AMINES; RADIOACTIVE WASTE VITRIFICATION;

BIOCATALYSIS; COFACTOR SPECIFICITY; IMINE REDUCTASE; OXIDATIVE DEAMINATION; RATIONAL DESIGN;

ENZYMES;

AMINE; NADPH DEPENDENT IMINE REDUCTASE; OXIDOREDUCTASE; PHOSPHATE; REDUCED NICOTINAMIDE ADENINE DINUCLEOTIDE; UNCLASSIFIED DRUG; BACTERIAL PROTEIN; IMINE; IMMOBILIZED ENZYME; NICOTINAMIDE ADENINE DINUCLEOTIDE; RECOMBINANT PROTEIN;

ARTICLE; BIOCATALYSIS; BIOTRANSFORMATION; CELL FREE SYSTEM; CELL LYSATE; CONTROLLED STUDY; DEAMINATION; ENZYME ACTIVITY; ENZYME IMMOBILIZATION; ENZYME METABOLISM; ENZYME PURIFICATION; ENZYME SPECIFICITY; NONHUMAN; PRIORITY JOURNAL; STREPTOMYCES; CHEMISTRY; ENZYMOLOGY; ESCHERICHIA COLI; GENETICS; METABOLISM; MOLECULAR MODEL; SITE DIRECTED MUTAGENESIS;

BACTERIAL PROTEINS; DEAMINATION; ENZYMES, IMMOBILIZED; ESCHERICHIA COLI; IMINES; MODELS, MOLECULAR; MUTAGENESIS, SITE-DIRECTED; NAD; OXIDOREDUCTASES; RECOMBINANT PROTEINS; STREPTOMYCES;

EID: 84969166562     PISSN: 01681656     EISSN: 18734863     Source Type: Journal    
DOI: 10.1016/j.jbiotec.2016.05.006     Document Type: Article

References (47)

1. Abrahamson M.J., Vazquez-Figueroa E., Woodall N.B., Moore J.C., Bommarius A.S. Development of an amine dehydrogenase for synthesis of chiral amines. Angew. Chem. Int. Ed. 2012, 51:3969-3972.
2. Bashiri G., Squire C.J., Moreland N.J., Baker E.N. Crystal structures of F-420-dependent glucose-6-phosphate dehydrogenase FGD1 involved in the activation of the anti-tuberculosis drug candidate PA-824 reveal the basis of coenzyme and substrate binding. J. Biol. Chem. 2008, 283:17531-17541.
3. Bornscheuer U.T. Immobilizing enzymes: how to create more suitable biocatalysts. Angew. Chem. Int. Ed. 2003, 42:3336-3337.
4. Breuer M., Ditrich K., Habicher T., Hauer B., Kesseler M., Stürmer R., Zelinski T. Industrial methods for the production of optically active intermediates. Angew. Chem. Int. Ed. 2004, 43:788-824.
5. Buchholz K., Klein J. Characterization of immobilized biocatalysts. Methods Enzymol. 1987, 135:3-30.
6. Buchholz K., Kasche V., Bornscheuer U.T. Biocatalysts and Enzyme Technology 2005, Wiley-VCH, Weinheim.
7. Cassimjee K.E., Kadow M., Wikmark Y., Humble M.S., Rothstein M.L., Rothstein D.M., Bäckvall J.E. A general protein purification and immobilization method on controlled porosity glass: biocatalytic applications. Chem. Commun. 2014, 50:9134-9137.
8. Gamenara D., Domínguez de Maria P. Enantioselective imine reduction catalyzed by imine reductases and artificial metalloenzymes. Org. Biomol. Chem. 2014, 12:2989-2992.
9. Gand M., Müller H., Wardenga R., Höhne M. Characterization of three novel enzymes with imine reductase activity. J. Mol. Catal. B 2014, 110:126-132.
10. Ghislieri D., Turner N.J. Biocatalytic approaches to the synthesis of enantiomerically pure chiral amines. Top. Catal. 2014, 57:284-300.
11. Girardin M., Ouellet S.G., Gauvreau D., Moore J.C., Hughes G., Devine P.N., O'shea P.D., Campeau L.-C. Convergent kilogram-scale synthesis of dual orexin receptor antagonist. Org. Process Res. Dev. 2013, 17:61-68.
12. Grisshammer R., Tucker J. Quantitative evaluation of neurotensin receptor purification by immobilized metal affinity chromatography. Protein Expr. Purif. 1997, 11:53-60.
13. Grogan G., Turner N.J. InspIRED by nature: NADPH-dependent imine reductases (IREDs) as catalysts for the preparation of chiral amines. Chem. Eur. J. 2016, 22:1900-1907.
14. Heath R.S., Pontini M., Hussain S., Turner N.J. Combined imine reductase and amine oxidase catalyzed deracemization of nitrogen heterocycles. Chemcatchem 2015, 10.1002/cctc.201500822.
15. Homaei A.A., Sariri R., Vianello F., Stevanato R. Enzyme immobilization: an update. J. Chem. Biol. 2013, 6:185-205.
16. Hsieh S.Y., Binanzer M., Kreituss I., Bode J.W. Expanded substrate scope and catalyst optimization for the catalytic kinetic resolution of N-heterocycles. Chem. Commun. 2012, 48:8892-8894.
17. Huber T., Schneider L., Präg A., Gerhardt S., Einsle O., Müller M. Direct reductive amination of ketones: structure and activity of S-selective imine reductases from Streptomyces. Chemcatchem 2014, 6:2248-2252.
18. Katzberg M., Skorupa-Parachin N., Gorwa-Grauslund M.F., Bertau M. Engineering cofactor preference of ketone reducing biocatalysts: a mutagenesis study on a γ-diketone reductase from the yeast Saccharomyces cerevisiae serving as an axample. Int. J. Mol. Sci. 2010, 11:1735-1758.
19. Khan F., He M.Y., Taussig M.J. Double-hexahistidine tag with high-affinity binding for protein immobilization, purification, and detection on Ni-nitrilotriacetic acid surfaces. Anal. Chem. 2006, 78:3072-3079.
20. Kohls H., Steffen-Munsberg F., Höhne M. Recent achievements in developing the biocatalytic toolbox for chiral amine synthesis. Curr. Opin. Chem. Biol. 2014, 19:180-192.
21. Kroutil W., Fischereder E.M., Fuchs C.S., Lechner H., Mutti F.G., Pressnitz D., Rajagopalan A., Sattler J.H., Simon R.C., Siirola E. Asymmetric preparation of prim-, sec-, and tert-amines employing selected biocatalysts. Org. Process Res. Dev. 2013, 17:751-759.
22. Leipold F., Hussain S., Ghislieri D., Turner N.J. Asymmetric reduction of cyclic imines catalyzed by a whole-cell biocatalyst containing an (S)-imine reductase. Chemcatchem 2013, 5:3505-3508.
23. Leipold F., Hussain S., France S.P., Turner N.J. Imine reductases. Science of Synthesis: Biocatalysis in Organic Synthesis 2015, 359-382. Thieme, Stuttgart. K. Faber, W.-D. Fessner, N.J. Turner (Eds.).
24. Li C., Xiao J. Asymmetric hydrogenation of cyclic imines with an ionic Cp*Rh(III) catalyst. J. Am. Chem. Soc. 2008, 130:13208-13209.
25. Li W., Chou S.C., Khullar A., Gerratana B. Cloning and characterization of the biosynthetic gene cluster for tomaymycin, an SJG-136 monomeric analog. Appl. Environ. Microb. 2009, 75:2958-2963.
26. Li H., Luan Z.J., Zheng G.W., Xu J.H. Efficient synthesis of chiral indolines using an imine reductase from Paenibacillus lactis. Adv. Synth. Catal. 2015, 357:1692-1696.
27. Man H., Wells E., Hussain S., Leipold F., Hart S., Turkenburg J.P., Turner N.J., Grogan G. Structure, activity and stereoselectivity of NADPH-dependent oxidoreductases catalysing the S-selective reduction of the imine substrate 2-methylpyrroline. Chembiochem 2015, 16:1052-1059.
28. Mitsukura K., Suzuki M., Tada K., Yoshida T., Nagasawa T. Asymmetric synthesis of chiral cyclic amine from cyclic imine by bacterial whole-cell catalyst of enantioselective imine reductase. Org. Biomol. Chem. 2010, 8:4533-4535.
29. Mitsukura K., Suzuki M., Shinoda S., Kuramoto T., Yoshida T., Nagasawa T. Purification and characterization of a novel (R)-imine reductase from Streptomyces sp GF3587. Biosci. Biotechnol. Biochem. 2011, 75:1778-1782.
30. Mitsukura K., Kuramoto T., Yoshida T., Kimoto N., Yamamoto H., Nagasawa T. A NADPH-dependent (S)-imine reductase (SIR) from Streptomyces sp GF3546 for asymmetric synthesis of optically active amines: purification, characterization, gene cloning, and expression. Appl. Microbiol. Biotechnol. 2013, 97:8079-8086.
31. Mutti F.G., Knaus T., Scrutton N.S., Breuer M., Turner N.J. Conversion of alcohols to enantiopure amines through dual-enzyme hydrogen-borrowing cascades. Science 2015, 349:1525-1529.
32. Nakano T., Miyake K., Endo H., Dairi T., Mizukami T., Katsumata R. Identification and cloning of the gene involved in the final step of chlortetracycline biosynthesis in Streptomyces aureofaciens. Biosci. Biotechnol. Biochem. 2004, 68:1345-1352.
33. Nobili A., Gall M.G., Pavlidis I.V., Thompson M.L., Schmidt M., Bornscheuer U.T. Use of small but smart libraries to enhance the enantioselectivity of an esterase from Bacillus stearothermophilus towards tetrahydrofuran-3-yl acetate. FEBS J. 2013, 280:3084-3093.
34. Nugent T.C., El-Shazly M. Chiral amine synthesis - Recent developments and trends for enamide reduction, reductive amination, and imine reduction. Adv. Synth. Catal. 2010, 352:753-819.
35. Paul C.E., Gargiulo S., Opperman D.J., Lavandera I., Gotor-Fernandez V., Gotor V., Taglieber A., Arends I.W.C.E., Hollmann F. Mimicking nature: synthetic nicotinamide cofactors for CC bioreduction using enoate reductases. Org. Lett. 2013, 15:180-183.
36. Paul C.E., Tischler D., Riedel A., Heine T., Itoh N., Hollmann F. Nonenzymatic regeneration of styrene monooxygenase for catalysis. ACS Catal. 2015, 5:2961-2965.
37. Rodríguez-Mata M., Frank A., Wells E., Leipold F., Turner N.J., Hart S., Turkenburg J.P., Grogan G. Structure and activity of NADPH-dependent reductase Q1EQE0 from Streptomyces kanamyceticus, which catalyses the R-selective reduction of an imine substrate. Chembiochem 2013, 14:1372-1379.
38. Scheller P.N., Fademrecht S., Hofelzer S., Pleiss J., Leipold F., Turner N.J., Nestl B.M., Hauer B. Enzyme toolbox: novel enantiocomplementary imine reductases. Chembiochem 2014, 15:2201-2204.
39. Scheller P.N., Lenz M., Hammer S.C., Hauer B., Nestl B. Imine reductase-catalyzed intermolecular reductive amination of aldehydes and ketones. Chemcatchem 2015, 7:3239-3242.
40. Schrittwieser J.H., Velikogne S., Kroutil W. Biocatalytic imine reduction and reductive amination of ketones. Adv. Synth. Catal. 2015, 357:1655-1685.
41. Sheldon R.A., van Pelt S. Enzyme immobilisation in biocatalysis: why, what and how. Chem. Soc. Rev. 2013, 42:6223-6235.
42. Steinhauer C., Wingren C., Khan F., He M.Y., Taussig M.J., Borrebaeck C.A.K. Improved affinity coupling for antibody microarrays: engineering of double-(His)(6)-tagged single framework recombinant antibody fragments. Proteomics 2006, 6:4227-4234.
43. +-dependent l-serine dehydrogenase. J. Biol. Chem. 2012, 287:1874-1883.
44. Turner N.J. A reduction of CN to CHNH using enzymes and microorganisms. Comprehensive Organic Synthesis II 2014, 328-338. Elsevier, Amsterdam. P. Knochel (Ed.).
45. Welsch M.E., Snyder S.A., Stockwell B.R. Privileged scaffolds for library design and drug discovery. Curr. Opin. Chem. Biol. 2010, 14:347-361.
46. Wetzl D., Berrera M., Sandon N., Fishlock D., Ebeling M., Müller M., Hanlon S., Wirz B., Iding H. Expanding the imine reductase toolbox by exploring the bacterial protein-sequence space. Chembiochem 2015, 16:1749-1756.
47. Wetzl D., Gand M., Ross A., Müller H., Matzel P., Hanlon S.P., Müller M., Wirz B., Höhne M., Iding H. Asymmetric reductive amination of ketones catalyzed by imine reductases. ChemCatChem 2016, (accepted 29.04.2016). 10.1002/cctc.201600384.