Modulation of the properties of penicillin G acylase by acyl donor substrates during N-protection of amino compounds

Enzyme and Microbial Technology

Volumn 22, Issue 7, 1998, Pages 583-587

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

^a CSIC   (Spain)

Author keywords

Enzyme modulation; Enzymes (in fine chemistry); Optically pure compound synthesis; Penicillin G acylase; Protection of amino compounds

Indexed keywords

ADSORPTION; AMINES; AMINO ACIDS; ANTIBIOTICS; CATALYSIS; CATALYST ACTIVITY; DERIVATIVES; ENZYMES; ESTERS; HYDROLYSIS;

ENZYMIC PROTECTION; HYDROXYLAMINE; PENICILLIN G ACYLASE;

BIOSYNTHESIS;

AMIDASE; AMINE; AMINO ACID; ESTER; HYDROLASE; MANDELIC ACID; METHYL GROUP; PENICILLIN G; PHENYLGLYCINE; TRANSFERASE;

ARTICLE; ENZYME SUBSTRATE; PH; STEREOSPECIFICITY; TEMPERATURE;

EID: 0032524016     PISSN: 01410229     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0141-0229(98)00239-7     Document Type: Article

References (25)

1. Shewale J.G., Deshpande B.S., Sudhakaran V.K., Ambedkar S.S. Penicillin acylases Application and potential . 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. Drugs and Pharmaceutical Sciences 22. 1984;177-224 Marcel Decker, New York.
3. Fernandez-Lafuente R., Rosell C.M., Guisan J.M. Enzyme reaction engineering Synthesis of antibiotics catalyzed by stabilized penicillin G acylase in the presence of organic cosolvents . Enzyme Microb. Technol. 13:1991;888-905.
4. Fernandez-Lafuente R., Alvaro G., Blanco R.M., Guisan J.M. Equilibrium controlled synthesis of cephalothin in monophasic water-organic cosolvents systems catalyzed by stabilized derivatives of penicillin G acylase. Appl. Biochem. Biotechnol. 27:1991;75-84.
5. Fernandez-Lafuente R., Rosell C.M., Piatkowska B., Guisan J.M. Synthesis of antibiotics (cephaloglycin) catalyzed by penicillin G acylase. Evaluation and optimization of different synthetic approaches. Enzyme Microb. Technol. 17:1996;517-523.
6. Fernandez-Lafuente R., Rosell 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.
7. Waldman H. Der Phenylacetyl-(PhAc)-rest als enzymatich ablosbare schutzgruppe fur peptide und kolenhydrate Selektive scutzgruppenabspaltungen mil penicillin-acylase . Liebegs Ann. Chem. 1988;1175-1180.
8. Waldman H. A new access to chiral 2-furylcarbinols by enantioselective hydrolysis with penicillin acylase. Tetrahedran Lett. 30:1989;3057-3058.
9. Fuganti C., Grasselli P., Seneci P.F., Servi S. Immobilised benzylpenicillin acylase Application to the synthesis of optically active forms of carnitin and propanalol . Tetrahedran Lett. 27:1986;2061-2062.
10. Kasche, V., Haufler, U., and Zollner, R. Kinetic studies on the mechanism of the penicillin amidase-catalyzed synthesis of ampicillin and benzylpenicillin. Hoppe-Seyler's Z. Physiol. Chem. 365, 1435-1443.
11. 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.
12. 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.
13. Kasche V., Haufler U., Riechman L. Equilibrium and kinetically controlled synthesis with enzymes Semisynthesis of penicillins and peptides . Meth. Enzymol. 136:1987;280-292.
14. Hyun C.K., Kim J.H., Kim Y.J. Effect of water activity on enzymatic synthesis of cephalexin. Biotechnol. Lett. 11:1989;537-540.
15. 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.
16. Kim M.G., Lee S.B. Penicillin acylase-catalyzed synthesis of pivampicillin Effect of reaction variables and organic solvents . J. Mol. Cat. B: Enzym. 1:1996;71-80.
17. 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: Enzym. 1:1996;181-190.
18. 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: Enzym. 1:1996;201-211.
19. Martin J., Manchego J.M., Arche R. Inactivation of penicillin acylase from K. citrophila by N-ethoxycarbonyl-2-ethoxy-2-2 dihydroquinoline A case of time-dependent noncovalent enzyme inhibition . Biochem. J. 291:1993;907-914.
20. Siewinsky M., Kuropatwa M., Szewczuk A. Phenylalkylsulfonyl derivatives as covalent inhibitors of penicillin acylase. Hoppe-Seyler's Z. Physiol. Chem. 635:1984;829-837.
21. Duggleby H.J., Tolley S.P., Hill C.P., Dodson E.J., Dodson G., Moody C.E. Penicillin acylase has a single amino acid catalytic center. Nature. 373:1995;264-268.
22. 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.
23. 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.
24. Guisan J.M. Agarose-aldehyde gels as supports for immobilization-stabilization of enzymes. Enzyme Microb. Technol. 10:1987;375-382.
25. Alvaro G., Fernandez-Lafuente R., Blanco R.M., Guisan J.M. Immobilisation-stabilisation of penicillin G acylase from E. coli. Appl. Biochem. Biotechnol. 26:1990;181-195.