Enzymatic synthesis of amoxicillin with immobilized penicillin G acylase

Scientia Iranica

Volumn 17, Issue 1 C, 2010, Pages 106-113

  Alemzadeh, I ^a   Borghei, G ^a   Vafi, L ^a   Roostaazad, R ^a  

^a SHARIF UNIVERSITY OF TECHNOLOGY   (Iran)

Author keywords

Amoxicillin; Aqueous medium; Enzyme content; Penicillin G acylase

Indexed keywords

ENZYMES; ESTERS; SUBSTRATES;

AMOXICILLIN; AQUEOUS MEDIUM; ENZYME CONCENTRATIONS; IMMOBILIZED PENICILLIN G ACYLASE; PENICILLIN G ACYLASE; PHENYLGLYCINE METHYL ESTERS; SUBSTRATE CONCENTRATIONS; TEMPERATURE VARIATION;

DRUG PRODUCTS;

ANTIBIOTICS; AQUEOUS SOLUTION; BIOCHEMICAL COMPOSITION; ENZYME ACTIVITY; PH; TEMPERATURE EFFECT;

EID: 79951639501     PISSN: 10263098     EISSN: None     Source Type: Journal    
DOI: None     Document Type: Article

References (28)

1. Wegman, M., Janssen, M., Rantwijk, F. and Sheldon, R. "Towards biocatalytic synthesis of B-Lactam antibiotics", Adv. Synth. Catal, 343, pp. 559-576 (2001). (Pubitemid 33679771)
2. Ekabder, R. P. "Industrial production of β-lactam", Microbiol Biotechnol, 61, pp. 385-392 (2003).
3. Goncalves, L. R. B., Fernandez-Lafuente, R., Guisan, J. M., Giordano, R. and Giordano, R. C. "Inhibitory effects in the side reactions occurring during the enzymic synthesis of amoxicillin: P-hydroxyphenylglycine methyl ester and amoxicillin hydrolysis", Biotechnol. Appl. Biochem, 38, pp. 77-85 (2003). (Pubitemid 36980632)
4. Ulijn, R. V., De Martin, L., Hailing, P. J., Moore, B. O. and Janssen, A. E. M. "Enzymatic synthesis of B-lactam antibiotics via direct condensation, biotechnology", 99, pp. 215-222 (2002).
5. Goncalves, L. R. B., Sousa, R., Fernandez-Lafuente, R., Guisan, J. M., Giordano, R. and Giordano, R. C. "Enzymatic synthesis of amoxicillin", Biotechnol Bioeng, 80, pp. 622-631 (2002).
6. Diender, M. B., Straathof, A. J. J., Can der Does, T., Zomerdijk, M. and Heijnen, J. J. "Course of PH during the formation of amoxicillin by a suspension to suspension reaction", Enzyme and Microbial Technology, 27, pp. 576-582 (2000).
7. Norouzian, D., Javadpour, S., Moazami, N. and Akbarzadeh, A. "Immobolizitaion of whole cell penicillin G acylase in open pore gelatin matrix", Enzyme and Microbial Technology, 30, pp. 26-29 (2000). (Pubitemid 34072926)
8. Aguirre, C., Opazo, P., Venegas, M., Riverso, R. and Illanes, A. "Low temperature effect on production of ampicillin and cephalexin in ethylene gycol medium with immobilized penicillin acylase", Process Biochemistry, 41, pp. 1924-1931 (2006). (Pubitemid 44118789)
9. Illanes, A. and Fajardo, A. "Kinetically controlled synthesis of ampicillin with immobilized penicillin acylase in the presence of organic cosolvents", Molecular Catalysis B: Enzymatic, 11, pp. 587-595 (2001). (Pubitemid 32114242)
10. Ferreura, A. L. O., Giordano, R. L. C., Giordano, R. C. "Improving selectivity and productivity of the enzymatic synthesis of ampicillin with immobilized penicillin G acylase", Chem. Eng, 21, p. 4(2004).
11. Paloma, M., Enobakhare, Y. and Torrado, G. "Release of amoxicillin from polyionic complexes of chitosan and poly (acrylic acid) ", Biomaterials, 24, pp. 1499-1506 (2003).
12. Youshko, M. I., Moody, H. M., Bukhanov, A. L., Boosten, W. H. J, and Svedas, V. K. "Penicillin acylasecatalyzed synthesis of B-lactam antiobiotics in highly condensed aqueous systems: Beneficial impact of kinetic substrate supersaturation", Biotechnol Bioeng, 85, pp. 323-329 (2004). (Pubitemid 38182225)
13. Youshko, M. I., Van Langen, L. M., Vromm, E., Van Rantwijk, F., Sheldon, R. A. and Svedas, V. K. "Highly efficient synthesis of ampicillin in an aqueous solutionprecipitate system: Repetitive addition of substrates in a semicontinuous process", Biotechnol Bioeng, 73, pp. 426-430 (2001). (Pubitemid 32493238)
14. Terreni, M., Ubiali, D., Pagani, G. and Hernandez-Justiz, O. "Penicillin G acylase catalyzed acyaltion of 7-AC A in aqueous two-phase systems", Enzyme and Microbial Technology, 36, pp. 672-679 (2005).
15. Schroen, C. G. P. H., Nerstrasz, V. A., Kroon, P. J., Bosnia, R. and Janssen, A. E. M. "Thermodynamically controlled synthesis of B-lactam antibiotics. Equilibrium concentrations and side-chain properties", Enzyme and Microbial Technology, 24, pp. 498-506 (1999). (Pubitemid 29219586)
16. Illanes, A., Altamirano, C., Fuentes, M., Zamorano, F. "Synthesis of cephalexin in organic medium at high substrate concentrations and low enzyme to substrate ratio", Molecular Catalysis B: Enzymatic, 35, pp. 45-51 (2005). (Pubitemid 40933747)
17. Sio, C. F. and Quax, W. J. "Improved B-lactam acylases and their use as industrial biocatalysts", Biotechnology, 15, pp. 349-355 (2004). (Pubitemid 39028914)
18. Schroen, C. G. P. H., Mohy Eldin, M. S., Janssen, A. E. M., Mita, G. D. and Tramper, J. "Cephalexin synthesis by immobilized penicillin acylase under nonisothermal conditions", Molecular Catalysis B, 15, pp. 163-172 (2001). (Pubitemid 32913153)
19. Illanes, A., Anfari, M. S., Altamirano, C. and Aguirre, C. "Optimization of cephalexin synthesis with immobilized penicillin acylase in ethylene glycol medium at low temperatures", Molecular Catalysis B: Enzymatic, 30, pp. 95-103 (2004). (Pubitemid 38597106)
20. Illanes, A., Cabrera, Z., Wilson, L., Aguirre, C. "Synthesis of cephalecin in ethylene glycol with glyocylagarose immobilised penicillin acylase: temperature and pH optimization", Process Biochemistry, pp. 111-117 (2003). (Pubitemid 37399564)
21. Guisan, J. "Aldehyde-agarose gels as activated supports for immobilization-stabilization of enzymes", Enzyme Microb. Technol, 10, p. 375(1988).
22. Alvaro, G., Fernandez-Lafuente, R., Blanco, R. M. and Guisan, J. "Synthesis of antibiotics catalysed by stabilized penicillin G acylase in the presence of organic cosolvents", Biochemistry and Biotechnology, 26, p. 181(1990).
23. Iturra, M., Zamorano, C. and Uanes, A. "Crosslinked penicillin acylase aggregates for synthesis of β-lactam antibiotics in organic medium", Biochemistry and Biotechnology, 15, p. 25(2003).
24. Roche, Molecular Biochemicals Industry, p. 41(1999).
25. Ospina, S., Barzana, E., Ramirez, O. T. and Lopez-Munguia, A. "Effect of pH in the synthesis of ampicillin by penicillin acylase", Enzyme Microb. Technol, 19, pp. 462-469 (1996). (Pubitemid 26366428)
26. Goncalves, L. R. B, Fernandez-Lafuente, R, Guisan, J. M. and Giordano, R. L. C. "A kinetic study of the synthesis of amoxicillin using penicillin G acylase immobilized on agarose", Biochem Biotechnol, 84-86, pp. 931-945 (2000). (Pubitemid 30349522)
27. Youshko, M. I., Langen, L. M., Vroom, E., Moody, H. M., Rantwijk, F. and Sheldon, R. A. "Penicillin acylasecatalyzed synthesis of ampicillin in "aqueous solutionprecipitate" systems. High substrate concentration and supersaturation effect", Molecular Catalysis B: Enzymatic, 10, pp. 509-515 (2000). (Pubitemid 30628636)
28. Abedi, D., Korbekandi, H., Mostafavi, S., Fazeli, M. and Mostafavi, P. "Effect of co-solvent on the kinetically controlled synthesis of amoxicillin with immobilized penicillin G acylase", AAPS National Biotechnology Conference, p. 1(2008).