The presence of methanol exerts a strong and complex modulation of the synthesis of different antibiotics by immobilized Penicillin G acylase

Enzyme and Microbial Technology

Volumn 23, Issue 5, 1998, Pages 305-310

  Fernandez Lafuente R ^a   Rosell, C M ^a   Guisan J M ^a  

^a CSIC   (Spain)

Author keywords

Modulation of enzymes; Penicillin G acylase; Synthesis of antibiotics

Indexed keywords

ACYLATION; ANTIBIOTICS; BIOSYNTHESIS; CATALYSIS; CATALYST ACTIVITY; CONFORMATIONS; ENZYME INHIBITION; ESTERS; HYDROLYSIS; METHANOL; MOLECULAR STRUCTURE; ORGANIC SOLVENTS;

MANDELIC ACID METHYL ESTER; PHENYLGLYCINE METHYL ESTER;

ENZYME IMMOBILIZATION;

AMIDASE; ANTIBIOTIC AGENT; MANDELIC ACID; METHANOL; PENICILLIN G; PHENYLGLYCINE;

ACYLATION; ARTICLE; DRUG SYNTHESIS; ENZYME IMMOBILIZATION; HYDROLYSIS;

EID: 0032189174     PISSN: 01410229     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0141-0229(98)00053-2     Document Type: Article

References (23)

1. Shewale J.G., Deshpande B.S., Sudhakaran V.K., Ambedkar S.S. Penicillin acylases Application and potentials . Process Biochem. Int. 6:1990;97-103.
2. Sadvige T.A. Enzymatic conversions used in the production of penicillins and cephalosporins. Vandamme E.J. Biotechnology of Industrial Antibiotics. 22:1984;177-224 Marcel Decker, New York.
3. Kasche V. Mechanism and yields in enzyme catalysed equilibrium and kinetically controlled synthesis of beta-lactamic antibiotics, peptides and other condensation products. Enzyme Microb. Technol. 8:1986;2-16.
4. Kasche V., Haufler U., Riechman L. Equilibrium and kinetically controlled synthesis with enzymes Semisynthesis of penicillins and peptides . Methods Enzymol. 136:1987;280-292.
5. Fernandez-Lafuente R., Rosell C.M., Guisan J.M. Enzyme reaction engineering Synthesis of antibiotics catalysed by stabilised penicillin G acylase in the presence of organic cosolvents . Enzyme Microb. Technol. 13:1991;888-905.
6. Fernandez-Lafuente R., Alvaro G., Blanco R.M., Guisan J.M. Equilibrium controlled synthesis of cephalothin in monophasic water-organic cosolvents systems catalysed by stabilised derivatives of penicillin G acylase. Appl. Biochem. Biotechnol. 27:1991;75-84.
7. Fernandez-Lafuente R., Rossell C.M., Guisan J.M. Dynamic reaction design of enzymatic biotransformations in organic media Equilibrium controlled synthesis of antibiotics by penicillin G acylase . Biotechnol. Appl. Biochem. 24:1996;139-143.
8. Fernandez-Lafuente R., Rosell C.M., Piatkowska B., Guisan J.M. Synthesis of antibiotics (cephaloglycin) catalysed by penicillin G acylase. Evaluation and optimisation of different synthetic approaches. Enzyme Microb. Technol. 17:1996;517-523.
9. Fernandez-Lafuente R., Rosell C.M., Guisan J.M. The use of stabilised penicillin acylase derivatives improves the design of kinetically controlled synthesis. J. Mol. Cat. 101:1995;91-97.
10. Fernandez-Lafuente R., Guisan J.M., Pregnolato M., Terreni M. Chemoenzymatic one pot synthesis of cefazolin from cephalosporin c in fully aqueous medium involving three consecutive biotransformations catalyzed by D-amino acid oxidase, glutaryl acylase, and penicillin G acylase. Tetrahedrum Lett. 38:1997;4893-4896.
11. Kasche V., Calunsky B. Ionic strength and pH effects in the kinetically controlled synthesis of benzyl penicillin by nucleophilic deacylation of free and immobilised phenylacetyl-penicillin amidase with 6APA. Biochem. Biophys. Res. Commun. 4:1982;1215-1222.
12. Hyun C.K., Kim J.H., Kim Y.J. Effect of water activity on enzymatic synthesis of cephalexin. Biotechnol. Lett. 11:1989;537-540.
13. Kasche V., Haufler U., Zollner R. Kinetic studies on the mechanism of the penicillin amidase-catalysed synthesis of ampicillin and benzylpenicillin. Hoppe-Seyler's Z. Physiol. Chem. 365:1988;375-382.
14. Kasche V. Ampicillin and cephalexin synthesis catalyzed by E. coli penicillin amidase. Yield increase due to substrate recycling. Biotechnol. Lett. 7:1985;877-882.
15. Kim M.G., Lee S.B. Penicillin acylase-catalyzed synthesis of pivampicillin Effect of reaction variables and organic solvents . J. Mol. Cat. B: Enzymatic. 1:1996;71-80.
16. Kim M.G., Lee S.B. Effect of organic solvents on penicillin acylase-catalyzed reactions Interaction of organic solvents with enzymes . J. Mol. Cat. B: Enzymatic. 1:1996;181-190.
17. Kim M.G., Lee S.B. Penicillin acylase-catalyzed synthesis of lactam antibiotics in water-methanol mixtures Effect of cosolvent content and chemical nature of substrate on reaction rates . J. Mol. Cat. B: Enzymatic. 1:1996;201-211.
18. Guisan J.M. Agarose-aldehyde gels as supports for immobilization-stabilization of enzymes. Enzyme Microb. Technol. 10:1987;375-382.
19. Alvaro G., Fernandez-Lafuente R., Blanco R.M., Guisan J.M. Immobilization-stabilisation of penicillin G acylase from E. coli. Appl. Biochem. Biotechnol. 26:1990;181-195.
20. Rosell C.M., Fernandez-Lafuente R., Guisan J.M. Modification of enzyme properties by the use of inhibitors during their stabilisation by multipoint covalent attachment. Biocatal. Biotransform. 12:1995;67-76.
21. Fernandez-Lafuente R., Rosell C.M., Guisan J.M. The synthetic properties of penicillin G acylase are strongly modulated by different acyl donor substrates Synthesis of optically pure protected amino compounds . Enzyme Microb. Technol. 22:1998;583-587.
22. Guisan J.M., Bastida A., Cuesta C., Fernandez-Lafuente R., Rosell C.M. Immobilization-stabilization of chymotrypsin by covalent attachment to aldehyde-agarose gels. Biotechnol. Bioeng. 38:1991;1144-1152.
23. Guisan J.M., Alvaro G., Rosell C.M., Fernandez-Lafuente R. Industrial design of enzymic processes catalyzed by very active immobilized derivatives Utilization of diffusional limitations (gradients of pH) as a profitable tool in enzyme engineering . Biotechnol. Appl. Biochem. 20:1994;357-369.