Efficient preparation of enantiopure l-tert-leucine through immobilized penicillin G acylase catalyzed kinetic resolution in aqueous medium

Biochemical Engineering Journal

Volumn 83, Issue , 2014, Pages 116-120

  Liu, Weiming ^a   Luo, Jixing ^b   Zhuang, Xiaojian ^b   Shen, Wenhe ^b   Zhang, Yang ^a   Li, Shuang ^a   Hu, Yi ^a   Huang, He ^a  

^a NANJING TECH UNIVERSITY   (China)

^b Zhejiang Jiuzhou Pharmaceutical Co Ltd   (China)

Author keywords

L tert leucine; Biocatalysis; Bioprocess design; Immobilized penicillin G acylase; Optimization; Packed bed bioreactors

Indexed keywords

L-TERT-LEUCINE; BIOCATALYSIS; BIOPROCESS DESIGN; IMMOBILIZED PENICILLIN G ACYLASE; PACKED-BED BIOREACTORS;

AMINO ACIDS; BIOLOGICAL WATER TREATMENT; ENANTIOSELECTIVITY; ENZYMES; HYDROLYSIS; INDUSTRIAL APPLICATIONS; OPTIMIZATION; PACKED BEDS;

SUBSTRATES;

LEUCINE; PENICILLIN AMIDASE; TERT LEUCINE; UNCLASSIFIED DRUG;

ARTICLE; BIOCATALYSIS; ENANTIOMER; ENANTIOSELECTIVITY; ENZYME IMMOBILIZATION; HYDROLYSIS KINETICS; PACKED BED REACTOR; PH; PRIORITY JOURNAL; TEMPERATURE; THERMOSTABILITY;

EID: 84892527003     PISSN: 1369703X     EISSN: 1873295X     Source Type: Journal    
DOI: 10.1016/j.bej.2013.12.016     Document Type: Article

References (38)

1. Bommarius A.S., Schwarm M., Sting K., Kottenhahn M., Huthmacher K., Drauz K. Synthesis and use of enantiomerically pure tert-leucine. Tetrahedron Asymmetry 1995, 6:2851-2888.
2. Bommarius A.S., Schwarm M., Drauz K. Biocatalysis to amino acid-based chiral pharmaceuticals - examples and perspectives. J. Mol. Catal. B Enzym. 1998, 5:1-11.
3. Abderhalden E., Faust W., Haase E. Untersuchungen über das konfigurative verhalten von pseudoleucin bei der waldenschen umkehrung und über die abspaltung von halogen durch verdünntes alkali aus raumisomeren α-brom-β-trimethyl-propionyl-aminosäuren. Hoppe-Seyler's Z. Physiol. Chem. 1934, 228:187-197.
4. L-tert-leucine in series of two enzyme membrane reactors. Bioprocess Eng. 1996, 14:291-297.
5. Liese A., Seelbach K., Buchholz A., Haberland J. Processes. Industrial Biotransformations 2000, 103-106. Wiley-VCH, Weinheim. A. Liese, K. Seelbach, C. Wandrey (Eds.).
6. L-tert-leucine using a whole cell-catalyst. Eng. Life Sci. 2004, 4:573-576.
7. D-tert-leucine. Org. Lett. 2003, 5:3649-3650.
8. L-(S)-tert-leucine via a lipase catalysed dynamic resolution process. Tetrahedron Lett. 1995, 36:1113-1116.
9. Stelkes-Ritter U., Beckers G., Bommarius A., Drauz K., Güther K., Kottenhahn M., Schwarm M., Kula M.-R. Kinetics of peptide amidase and its application for the resolution of racemates. Biocatal. Biotransform. 1997, 15:205-219.
10. D-tert-leucine. Biosci. Biotechnol. Biochem. 2001, 65:1977-1980.
11. Agosta E., Caligiuri A., D'Arrigo P., Servi S., Tessaroa D., Canevotti R. Enzymatic approach to both enantiomers of N-Boc hydrophobic amino acids. Tetrahedron Asymmetry 2006, 17:1995-1999.
12. S. Grabley, R. Keller, M. Schlingmann, Method for the production of an immobilized acylase and its use, EP 0,141,223, 1987.
13. Liu S.-L., Wei D.-Z., Song Q.-X., Zhang Y.-W., Wang W.-D. Effect of organic cosolvent on kinetic resolution of tert-leucine by penicillin G acylase from Kluyvera citrophila. Bioprocess Biosyst. Eng. 2006, 28:285-289.
14. Liu S.-L., Song Q.-X., Wei D.-Z., Zhang Y.-W., Wang W.-D. Preparation of optically pure tert-leucine by penicillin G acylase-catalyzed resolution. Prep. Biochem. Biotechnol. 2006, 36:235-241.
15. Arroyo M., de la Mata I., Acebal C., Castillón M.P. Biotechnological applications of penicillin acylases: state-of-the-art. Appl. Microbiol. Biotechnol. 2003, 60:507-514.
16. Cheng S.-W., Wei D.-Z., SongF Q.-X. Extraction penicillin G acylase from Alcaligenes faecalis in recombinant Escherichia coli with cetyl-trimethylammoniumbromide. Biochem. Eng. J. 2006, 32:56-60.
17. Kheirolomoom A., Ardjmand M., Fazelinia H., Zakeri A. Clarification of penicillin G acylase reaction mechanism. Process Biochem. 2001, 36:1095-1101.
18. Baldaros E., D'Arrigo P., Pedrocchi-Fantoni G., Rosell C.M., Servi S., Tagliani A., Terreni M. Pen G acylase catalyzed resolution of phenylacetate esters of secondary alcohols. Tetrahedron Asymmetry 1993, 4:1031-1034.
19. Fadnavis N.W., Sharfuddin M., Vadivel S.K. Resolution of racemic 2-amino-1-butanol with immobilized penicillin G acylase. Tetrahedron Asymmetry 1999, 10:4495-4500.
20. Kumaraguru T., Fadnavis N.W. Resolution of racemic 4-hydroxy-2-cyclopentenone with immobilized penicillin G acylase. Tetrahedron Asymmetry 2012, 23:775-779.
21. Roche D., Prasad K., Repic O. Enantioselective acylation of β-aminoesters using penicillin G acylase in organic solvents. Tetrahedron Lett. 1999, 40:3665-3668.
22. L)-phenylglycine via isoelectrically-trapped penicillin G acylase. Biotechnol. Bioeng. 1998, 60:454-461.
23. Fadnavis N.W., Devi A.V., Jasti L.S. Resolution of racemic 2-chlorophenyl glycine with immobilized penicillin G acylase. Tetrahedron Asymmetry 2008, 19:2363-2366.
24. Xue Y.-P., Jiang T., Liu X., Zheng Y.-G. Efficient production of S-(+)-2-chlorophenylglycine by immobilized penicillin G acylase in a recirculating packed bed reactor. Biochem. Eng. J. 2013, 74:88-94.
25. van Langen L.M., Oosthoek N.H.P., Guranda D.T., van Rantwijk F., Svedas V.K., Sheldon R.A. Penicillin acylase-catalyzed resolution of amines in aqueous organic solvents. Tetrahedron Asymmetry 2000, 11:4593-4600.
26. Faber K., Ottolina G., Riva S. Selectivity-enhancement of hydrolase reactions. Biocatal. Biotransform. 1993, 8:91-132.
27. Li D.-C., Cheng S.-W., Wei D.-Z., Ren Y.-H., Zhang D.-R. Production of enantiomerically pure (S)-β-phenylalanine and (R)-β-phenylalanine by penicillin G acylase from Escherichia coli in aqueous medium. Biotechnol. Lett. 2007, 29:1825-1830.
28. Wolff A., Zhu L., Wong Y.W., Straathof A.J.J., Jongejan J.A., Heijnen J.J. Understanding the influence of temperature change and cosolvent addition on conversion rate of enzymatic suspension reactions based on regime analysis. Biotechnol. Bioeng. 1999, 62:125-134.
29. Philips R.S. Temperature modulation of the stereochemistry of enzymatic catalysis: prospects for exploitation. Trends Biotechnol. 1996, 14:13-16.
30. Ong A.L., Kamaruddin A.H., Bhatia S., Long W.S., Lim S.T., Kumari R. Performance of free Candida antarctica lipase B in the enantioselective esterification of (R)-ketoprofen. Enzyme Microb. Technol. 2006, 39:924-929.
31. Niersbach H., Kühne A., Tischer W., Weber M., Wedekind F., Plapp R. Improvement of the catalytic properties of penicillin G acylase from Escherichia coli ATCC 11105 by selection of a new substrate specificity. Appl. Microbiol. Biotechnol. 1995, 43:679-684.
32. Ulbrich R., Schellenberger A., Damerau W. Studies on the thermal inactivation of immobilized enzymes. Biotechnol. Bioeng. 1986, 28:511-522.
33. Zuza M.G., Siler-Marinkovic S.S., Knezevic Z.D. Preparation and characterization of penicillin acylase immobilized on Sepabeads EC-EP carrier. Chem. Ind. Chem. Eng. Q. 2007, 13:205-210.
34. Halim S.F.A., Kamaruddin A.H., Fernando W.J.N. Continuous biosynthesis of biodiesel from waste cooking palm oil in a packed bed reactor: optimization using response surface methodology (RSM) and mass transfer studies. Bioresour. Technol. 2009, 100:710-716.
35. Zhao T.T., Kim B.H., Hong S.I., Yoon S.W., Kim C.-T., Kim Y., Kim I.-H. Lipase-catalyzed production of pinolenic acid concentrate from pine nut oil using a recirculating packed bed reactor. J. Food Sci. 2012, 77:267-271.
36. Hama S., Yamaji H., Fukumizu T., Numata T., Tamalampudi S., Kondo A., Noda H., Fukuda H. Biodiesel-fuel production in a packed-bed reactor using lipase-producing Rhizopus oryzae cells immobilized within biomass support particles. Biochem. Eng. J. 2007, 34:273-278.
37. Yoshida A., Hama S., Tamadani N., Fukuda H., Kondo A. Improved performance of a packed-bed reactor for biodiesel production through whole-cell biocatalysis employing a high-lipase-expression system. Biochem. Eng. J. 2012, 63:76-80.
38. S. Grabley, Process for the racemization of optically active aminoacids, US 4,638,086, 1987.