Asymmetric hydrolysis of dimethyl phenylmalonate by immobilized penicillin G acylase from E. coli

Enzyme and Microbial Technology

Volumn 40, Issue 5, 2007, Pages 997-1000

  Cabrera, Zaida ^a   Lopez Gallego, Fernando ^a   Fernandez Lorente, Gloria ^a   Palomo, Jose M ^a   Montes, Tamara ^a   Grazu, Valeria ^a   Guisán, Jose M ^a   Fernández Lafuente, Roberto ^a  

^a INSTITUTO DE CATÁLISIS Y PETROLEOQUÍMICA   (Spain)

Author keywords

Asymmetric reactions; Desymmetrisation; Enzyme asymmetry; Enzyme selectivity; Partial hydrolysis; Prochiral compounds

Indexed keywords

ASYMMETRIC REACTIONS; DESYMMETRISATION; ENZYME ASYMMETRY; ENZYME SELECTIVITY; PARTIAL HYDROLYSIS; PROCHIRAL COMPOUNDS;

BIOCATALYSTS; CARBOXYLIC ACIDS; CATALYST ACTIVITY; ENZYME ACTIVITY; ESCHERICHIA COLI; HYDROLYSIS;

ESTERS;

AMIDASE; BACTERIAL ENZYME; DIMETHYL PHENYLMALONATE; MALONIC ACID DERIVATIVE; PENICILLIN G; PENICILLIN G ACYLASE; UNCLASSIFIED DRUG;

ARTICLE; ASYMMETRIC CATALYSIS; BIOCATALYST; CHIRALITY; ENANTIOMER; ENZYME IMMOBILIZATION; ESCHERICHIA COLI; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; HYDROLYSIS; NONHUMAN;

EID: 33847676407     PISSN: 01410229     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.enzmictec.2006.11.009     Document Type: Article

References (30)

1. Reetz M.T. Combinatorial and evolution-based methods in the creation of enantioselective catalysts. Angew Chem Int Ed Engl 40 (2001) 84-310
2. Glueck S.M., Mayer S.F., Krautil W., and Faber K. Advances in biocatalytic synthesis. Enzyme-triggered asymmetric cascade reactions. Pure Appl Chem 74 (2002) 2253-2257
3. Akai S., Naka T., Fujita T., Takebe Y., Tsujino T., and Kita Y. Efficient lipase-catalyzed enantioselective desymmetrization of prochiral 2,2-disubstituted 1,3-propanediols and meso 1,2-diols using 1-ethoxyvinyl 2-furoate Shuji. J Org Chem 67 2 (2002) 411-419
4. Tarui N., Nagano Y., Sakane T., Matsumoto K., Kawada M., Uchikawa O., et al. Kinetic resolution of an indan derivative using Bacillus sp. SUI-12: synthesis of a key intermediate of the melatonin receptor agonist TAK-375. J Biosci Bioeng 93 (2002) 44-47
5. Wiktelius D., Magnus J.J., Luthman K., and Kann N. A biocatalytic route to P-chirogenic compounds by lipase-catalyzed desymmetrization of a prochiral phosphine-borane. Org Lett 7 (2005) 4991-4994
6. Done S.H., Brannigan J.A., Moody P.C., and Hubbard R.E. Ligand-induced conformational change in penicillin acylase. J Mol Biol 284 (1998) 463-475
7. Svedas V.K., Savchenko M.V., Beltser A.I., and Guranda D.F. Enantioselective penicillin acylase-catalyzed reactions. Factors governing substrate and stereospecificity of the enzyme. Ann N Y Acad Sci 12 (1996) 659-669
8. Arroyo M., de la Mata I., Acebal C., and Castillón M.P. Biotechnological applications of penicillin acylases: state-of-the-art. Appl Microbiol Biotechnol 60 (2003) 507-514
9. Parmar A., Kumar H., Marwaha S.S., and Kennedy J.F. Advances in enzymatic transformation of penicillins to 6-aminopenicillanic acid (6-APA). Biotechnol Adv 18 (2000) 289-301
10. Giordano R.C., Ribeiro M.P.A., and Giordano R.L.C. Kinetics of β-lactam antibiotics synthesis by penicillin G acylase (PGA) from the viewpoint of the industrial enzymatic reactor optimization. Biotechnol Adv 24 (2006) 27-41
11. Abian O., Mato C., Palomo J.M., Fernández-Lorente G., Guisan J.M., and Fernandez-Lafuente R. Enantioselective synthesis of phenylacetamides in the presence of high organic solvent concentration catalyzed by stabilized penicillin G acylase. The effect of the acyl donor. Biotechnol Prog 20 (2004) 984-988
12. Guranda D.T., Van Lancen L.M., Van Rantwijk F., Sheldon R.A., and Svedas V.K. Highly efficient and enantioselective enzymatic acylation of aminesin aqueous medium. Tetrahedron Asymmetry 12 (2001) 1645-1650
13. Roche D., Prasad K., and Repic O. Enantioselectivity acylation of β-aminoesters using penicillin G acylase in organic solvents. Tetrahedron Lett 40 (1999) 3665-3668
14. Rochietti S., Urrutia A.S.V., Pregnolato M., Tagliani A., Guisán J.M., Fernández-Lafuente R.F., et al. Influence of the enzyme derivative preparation and substrate structure on enantioselectivity of penicillin G acylase. Enzyme Microb Technol 31 (2002) 88-93
15. Van Langen L.M., Oosthoek N.H.P., Guranda D.T., Van Rantwijk F., Svedas V.K., and Sheldon R.A. Penicillin acylase-catalyzed resolution of amines in aqueous organic solvents. Tetrahedron Asymmetry 11 (2000) 4593-4600
16. Waldmann H., Heuser A., and Schulze S. Selective enzymatic removal of protecting groups: the phenylacetamide as amino protecting group in phosphopeptide synthesis. Tetrahedron Lett 37 (1996) 8725-8728
17. Basso A., Braiuca P., Clementi S., Ebert C., Gardossi L., and Linda P. Computational analysis of the aminic subsite of PGA explains the influence of amine structure on enantioselectivity. J Mol Catal B: Enzyme 19-20 (2002) 423-430
18. Calleri E., Temporini G., Massolini G., and Caccialanza G. Penicillin G acylase-based stationary phases: analytical applications. J Pharm Biomed Anal 35 (2004) 243-258
19. De María P.D., Kossmann B., Potgrave N., Buchholz S., Trauthwein H., May O., et al. Improved process for the enantioselective hydrolysis of prochiral diethyl malonates catalyzed by pig liver esterase. Synlett (2005) 1746-1748
20. Klotz-Berendes B., Kleemiß W., Jegelka U., Schäfer H.J., and Kotila S. Enzymatic synthesis of optically active mono-alkylated malonic monoesters. Tetrahedron Asymmetry 8 (1997) 1821-1823
21. Toone E.J., and Jones J.B. Enzymes in organic synthesis 50. Probing the dimensions of the large hydrophobic binding region of the active site of pig liver esterase using substituted aryl malonate substrates. Tetrahedron Asymmetry 2 (1991) 1041-1052
22. Arzel P., Freida V., Weber P., and Fadel A. An easy access to (S)-pyrrolidinones and -pyrrolidines from chiral benzylic malonates. Tetrahedron Asymmetry 10 (1999) 3877-3881
23. Zhang S., and Bordwell F.G. Pig liver esterase catalyzed hydrolysis of dimethyl and diethyl 2-methyl-2-(o-nitrophenoxy)malonates. Tetrahedron Asymmetry 8 (1997) 425-443
24. Cabrera Z., Palomo J.M., Fernandez-Lorente G., Fernandez-Lafuente R., and Guisan J.M. Partial and enantioselective hydrolysis of diethyl phenylmalonate by immobilized preparations of lipase from Thermomyces lanuginos. Enzyme Microb Technol 40 (2007) 1280-1285
25. Guisán J.M. Aldehyde-agarose gels as activated supports for immobilization-stabilization of enzymes. Enzyme Microb Technol 10 (1988) 375-382
26. Mateo C., Abian O., Bernedo M., Cuenca E., Fuentes M., Fernandez-Lorente G., et al. Some special features of glyoxyl supports to immobilize proteins. Enzyme Microb Technol 37 (2005) 456-462
27. Fernández-Lafuente R., Rosell C.M., Piatkowska B., and Guisán J.M. Synthesis of antibiotics (CEPHALOGLYCIN) catalysed by penicillin G acylase: evaluation and optimization of different synthetic approaches. Enzyme Microb Technol 19 (1996) 9-14
28. Kallenberg A.I., van Rantwijk F., and Sheldon R.A. Immobilization of penicillin G acylase: the key optimum performance. Adv Synth Catal 347 (2005) 905-90624
29. Elander R.P. Industrial production of β-lactam antibiotics. Appl Microbiol Biotechnol 61 (2003) 385-392
30. van der Mey M., and de Vroom E. Substrate specificity of immobilized penicillin-G acylase. Bioorg Med Chem Lett 4 (1994) 345-348