Efficient production of S-(+)-2-chlorophenylglycine by immobilized penicillin G acylase in a recirculating packed bed reactor

Biochemical Engineering Journal

Volumn 74, Issue , 2013, Pages 88-94

  Xue, Ya Ping ^a   Jiang, Tao ^a   Liu, Xue ^a   Zheng, Yu Guo ^a  

^a ZHEJIANG UNIVERSITY OF TECHNOLOGY   (China)

Author keywords

Biocatalysis; Bioconversion; Immobilized penicillin G acylase; Optimization; Packed bed bioreactors; S (+) 2 Chlorophenylglycine

Indexed keywords

BIOCATALYSIS; EFFICIENT PRODUCTION; HEIGHT-TO-DIAMETER RATIO; IMMOBILIZED PENICILLIN G ACYLASE; PACKED-BED BIOREACTORS; S-(+)-2-CHLOROPHENYLGLYCINE; SEMICONTINUOUS OPERATION; SUBSTRATE CONCENTRATIONS;

BIOCONVERSION; CHEMICAL REACTORS; ENZYMES; KINETICS; OPTIMIZATION; PACKED BEDS; PRODUCTIVITY;

SUBSTRATES;

2 CHLOROPHENYLGLYCINE; GLYCINE DERIVATIVE; PENICILLIN AMIDASE; UNCLASSIFIED DRUG;

AMINO ACID SYNTHESIS; ARTICLE; CATALYSIS; CHEMICAL COMPOSITION; CONCENTRATION (PARAMETERS); ENANTIOMER; ENZYME ACTIVITY; ENZYME IMMOBILIZATION; ENZYME KINETICS; ENZYME SUBSTRATE; PACKED BED REACTOR; PH; PRIORITY JOURNAL; REACTION TIME; TEMPERATURE; THERMOSTABILITY;

EID: 84875795467     PISSN: 1369703X     EISSN: 1873295X     Source Type: Journal    
DOI: 10.1016/j.bej.2013.03.005     Document Type: Article

References (22)

1. Ferraboschi P., Mieri M.D., Galimberti F. Chemo-enzymatic approach to the synthesis of the antithrombotic clopidogrel. Tetrahedron:Asymmetry 2010, 21:2136-2141.
2. Fayed A.S., Weshahy S.A., Shehata M.A., Hassan N.Y., Pauwels J., Hoogmartens J., Schepdael A.V. Separation and determination of clopidogrel and its impurities by capillary electrophoresis. J. Pharmaceut. Biomed. 2009, 49:193-200.
3. E. Sajja, R.R., Anumula, G., Gilla, L.R. Madivada, Process for Preparing Clopidogrel, US 2007/0225320 A1, 2007.
4. Herbert J., Savi P., Maffrand J. Biochemical and pharmacological properties of clopidogrel: a new ADP receptor antagonist. Eur. Heart J. 1999, 20:31-40.
5. Campo G., Fileti L., Cesare N., Meliga E., Furgieri A., Russo F., Colangelo S., Brugaletta S., Ferrari R., Valgimigli M. Long-term clinical outcome based on aspirin and clopidogrel responsiveness status after elective percutaneous coronary intervention. J. Am. Coll. Cardiol. 2010, 56:1447-1455.
6. Wang W., Xue Y.P., Zheng Y.G. Research progress in synthesis of clopidogrel. Modern Chem. Ind. 2011, 31:30-34.
7. S.S.S. Lin, C.C. Chen, Process for prepartion of 2-chlorophenylglycine derivatives and enantiomerically separation, US 2004/0176637 A1, 2004.
8. O. Katoh, T. Uragaki, T. Nakamura, Process for producing optically active alpha-amino acid and optically active alpha-amino acid amide, WO 0187819, 2001.
9. S.O. Hwang, K.S. Kim, Y.J. Kim, Method for preparing clopidogrel and its derivatives, WO 2009/151256 A2, 2009.
10. 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.
11. Girelli A.M., Mattei E. Application of immobilized enzyme reactor in on-line high performance liquid chromatography: a review. J. Chromatogr. B 2005, 819:3-16.
12. Wang X., Liu X., Zhao C., Ding Y., Xu P. Biodiesel production in packed-bed reactors using lipase-nanoparticle biocomposite. Bioresour. Technol. 2011, 102:6352-6355.
13. Leng Y., Zheng P., Sun Z.H. Continuous production of l-phenylalanine from phenylpyruvic acid and l-aspartic acid by immobilized recombinant Escherichia coli SW0209-52. Process Biochem. 2006, 41:1669-1672.
14. Zhao 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.
15. Pan J.L., Syu M.J. A thermal study on the use of immobilized penicillin G acylase in the formation of 7-amino-3-deacetoxy cephalosporanic acid from cephalosporin G. J. Chem. Technol. Biotechnol. 2004, 79:1050-1056.
16. Ospina S.S., Lopez-Munguia A., Gonzalez R.L., Quintero R. Characterization and use of a penicillin acylase biocatalyst. J. Chem. Technol. Biotechnol. 1992, 53:205-213.
17. Abian O., Mateo C., Palomo J.M., Fernández-Lorente G., Guisán J.M., Fernández-Lafuente R. Enantioselective synthesis of phenylacetamides in the presence of high organic cosolvent concentrations catalyzed by stabilized penicillin G acylase. Effect of the acyl donor. Biotechnol. Prog. 2004, 20:984-988.
18. Phillips R.S. Temperature modulation of the stereochemistry of enzymatic catalysis: prospects for exploitation. Trends Biotechnol. 1996, 14:13-16.
19. Li D., Cheng S., Wei D., Ren Y., Zhang D. Production of enantiomerically pure S-ß-phenylalanine and R-ß-phenylalanine by penicillin G acylase from Escherichia coli in aqueous medium. Biotechnol. Lett. 2007, 29:1825-1830.
20. Zhang X., Xu J.H., Liu D., Pan J., Chen B. Construction and operation of a fibrous bed reactor with immobilized lactonase for efficient production of (R)- a-hydroxy- (-butyrolactone. Biochem. Eng. J. 2010, 50:47-53.
21. S. Grabley, Process for the racemization of opticaly active amnoacids, US 4,638,086, 1987.
22. Hita E., Robles A., Camacho B., González P.A., Esteban L., Jiménez M.J., Muñío M.M., Molina E. Production of structured triacylglycerols by acidolysis catalyzed by lipases immobilized in a packed bed reactor. Biochem. Eng. J. 2009, 46:257-264.