Improved β-lactam acylases and their use as industrial biocatalysts

Current Opinion in Biotechnology

Volumn 15, Issue 4, 2004, Pages 349-355

  Sio, Charles F ^a   Quax, Wim J ^a  

^a UNIVERSITY OF GRONINGEN   (Netherlands)

Author keywords

7 ACA; 7 ADCA; 7 aminocephalosporanic acid; 7 aminodesacetoxycephalosporanic acid; cephalosporin C; CPC; PAA; penicillin G acylase; PGA; phenyl acetic acid

Indexed keywords

BETA LACTAMASE;

ACYLATION; BIOCATALYST; CATALYSIS; CATALYST; CRYSTAL STRUCTURE; DRUG HYDROLYSIS; ENZYME IMMOBILIZATION; ENZYME SPECIFICITY; PRIORITY JOURNAL; PROTEIN ENGINEERING; RACEMIC MIXTURE; REVIEW; SITE DIRECTED MUTAGENESIS; STEREOCHEMISTRY; THREE DIMENSIONAL IMAGING;

AMIDOHYDROLASES; BACTERIA; BETA-LACTAMASES; CATALYSIS; CHEMICAL INDUSTRY; DRUG INDUSTRY; ENZYMES, IMMOBILIZED; PENICILLIN AMIDASE; PROTEIN ENGINEERING;

EID: 3543148392     PISSN: 09581669     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.copbio.2004.06.006     Document Type: Review

References (46)

1. R.P. Elander Industrial production of β-lactam antibiotics Appl Microbiol Biotechnol 61 2003 385 392
2. A. Bruggink, E.C. Roos and E. deVroom Penicillin acylase in the industrial production of β-lactam antibiotics Org Process Res Dev 2 1998 128 133
3. H.J. Duggleby, S.P. Tolley, C.P. Hill, E.J. Dodson, G. Dodson and P.C. Moody Penicillin acylase has a single-amino-acid catalytic center Nature 373 1995 264 268
4. M. Arroyo, I. de la Mata, C. Acebal and C.M. Pilar Biotechnological applications of penicillin acylases: state-of-the-art Appl Microbiol Biotechnol. 60 2003 507 514
5. K. Plhackova, S. Becka, F. Skrob and P. Kyslik Isolation and characterization of a new strain of Achromobacter sp with β-lactam antibiotic acylase activity Appl Microbiol Biotechnol 62 2003 507 516
6. F. Skrob, S. Becka, K. Plhackova, V. Fotopulosova and P. Kyslik Novel penicillin G acylase from Achromobacter sp CCM 4824 Enzyme Microb Technol 32 2003 738 744 Reports the isolation and characterization of a β-lactam acylase that shows high activity towards substrates with an α-amino group. In contrast to the α-amino acid ester hydrolases, this enzyme seems to be a 'true' β-lactam acylase, consisting of two dissimilar subunits and containing an N-terminal serine residue.
7. R. Torres-Guzman, I. de lM, J. Torres-Bacete, M. Arroyo, M.P. Castillon and C. Acebal Substrate specificity of penicillin acylase from Streptomyces lavendulae Biochem Biophys Res Commun 291 2002 593 597
8. J.J. Polderman-Tijmes, P.A. Jekel, E.J. de Vries, A.E. van Merode, R. Floris, J.M. Der Laan, T. Sonke and D.B. Janssen Cloning, sequence analysis, and expression in Escherichia coli of the gene encoding an α-amino acid ester hydrolase from Acetobacter turbidans Appl Environ Microbiol 68 2002 211 218
9. J.J. Polderman-Tijmes, P.A. Jekel, C.M. Jeronimus-Stratingh, A.P. Bruins, J.M. van der Laan, T. Sonke and D.B. Janssen Identification of the catalytic residues of α-amino acid ester hydrolase from Acetobacter turbidans by labeling and site-directed mutagenesis J Biol Chem 277 2002 28474 28482
10. T. Takahashi, Y. Yamazaki, K. Kato and M. Isono Enzymatic synthesis of cephalosporins J Am Chem Soc 94 1972 4035 4037
11. S. Yang, L.P. Zhou, H.X. Tang, J. Pan, X.J. Wu, H. Huang and Z.Y. Yuan Rational design of a more stable penicillin G acylase against organic cosolvent J Mol Catal B Enzym 18 2002 285 290
12. O. Abian, V. Grazu, J. Hermoso, R. Gonzalez, J.L. Garcia, R. Fernandez-Lafuente and J.M. Guisan Stabilization of penicillin G acylase from Escherichia coli: Site-directed mutagenesis of the protein surface to increase multipoint covalent attachment Appl Environ Microbiol 70 2004 1249 1251 An interesting approach for increasing the stability of a protein by site-directed mutagenesis, not by improving the stability of the protein itself but by enhancing the interaction with a stabilizing support.
13. W.B.L. Alkema, A.J. Dijkhuis, E. de Vries and D.B. Janssen The role of hydrophobic active-site residues in substrate specificity and acyl transfer activity of penicillin acylase Eur J Biochem 269 2002 2093 2100
14. Z. Zhou, A.H. Zhang, J.R. Wang, M.L. Chen, R.B. Li, S. Yang and Z.Y. Yuan Improving the specific synthetic activity of a penicillin G acylase using DNA family shuffling Acta Biochim Biophys Sin 35 2003 573 579
15. K. Fritz-Wolf, K.P. Koller, G. Lange, A. Liesum, K. Sauber, H. Schreuder, W. Aretz and W. Kabsch Structure-based prediction of modifications in glutarylamidase to allow single-step enzymatic production of 7-aminocephalosporanic acid from cephalosporin C Protein Sci 11 2002 92 103
16. B. Oh, M. Kim, J. Yoon, K. Chung, Y. Shin, D. Lee and Y. Kim Deacylation activity of cephalosporin acylase to cephalosporin C is improved by changing the side-chain conformations of active-site residues Biochem Biophys Res Commun 310 2003 19 27
17. C.F. Sio, A.M. Riemens, J.M. van der Laan, R.M.D. Verhaert and W.J. Quax Directed evolution of a glutaryl acylase into an adipyl acylase Eur J Biochem 269 2002 4495 4504
18. L.G. Otten, C.F. Sio, J. Vrielink, R.H. Cool and W.J. Quax Altering the substrate specificity of cephalosporin acylase by directed evolution of the β-subunit J Biol Chem 277 2002 42121 42127 Random mutagenesis of the β-subunit of cephalosporin acylase followed by selection on substrate derivatives resulted in several mutants that show an increased activity towards adipyl-7-ADCA. Several hot-spot residues that can be used to alter the substrate specificity were also identified.
19. L. Crawford, A.M. Stepan, P.C. McAda, J.A. Rambosek, M.J. Conder, V.A. Vinci and C.D. Reeves Production of cephalosporin intermediates by feeding adipic acid to recombinant Penicillium chrysogenum strains expressing ring expansion activity Biotechnology (NY) 13 1995 58 62
20. C.F. Sio, L.G. Otten, R.H. Cool and W.J. Quax Analysis of a substrate specificity switch residue of cephalosporin acylase Biochem Biophys Res Commun 312 2003 755 760
21. L.G. Otten, C.F. Sio, A.M.v.d. Sloot, R.H. Cool and W.J. Quax Mutational analysis of a key residue in the substrate specificity of a cephalosporin acylase Chem Bio Chem 5 2004 820 825
22. M. Morillas, C.E. Mcvey, J.A. Brannigan, A.G. Ladurner, L.J. Forney and R. Virden Mutations of penicillin acylase residue B71 extend substrate specificity by decreasing steric constraints for substrate binding Biochem J 371 2003 143 150
23. Y. Kim and W.G. Hol Structure of cephalosporin acylase in complex with glutaryl-7-aminocephalosporanic acid and glutarate: insight into the basis of its substrate specificity Chem Biol 8 2001 1253 1264
24. X. Huang, R. Zeng, X. Ding, X. Mao, Y. Ding, Z. Rao, Y. Xie, W. Jiang and G. Zhao Affinity alkylation of the Trp-B4 residue of the β-subunit of the glutaryl 7-aminocephalosporanic acid acylase of Pseudomonas sp. 130 J Biol Chem 277 2002 10256 10264
25. W. Zhang, X. Huang, G.P. Zhao and W.H. Jiang Affinity labeled glutaryl-7-amino cephalosporanic acid acylase C130 can hydrolyze the inhibitor during crystallization Biochem Biophys Res Commun 313 2004 555 558
26. Y. Kim, K. Yoon, Y. Khang, S. Turley and W.G. Hol The 2.0 crystal structure of cephalosporin acylase Structure 8 2000 1059 1068
27. J.K. Kim, I.S. Yang, S. Rhee, Z. Dauter, Y.S. Lee, S.S. Park and K.H. Kim Crystal structures of glutaryl 7-aminocephalosporanic acid acylase: insight into autoproteolytic activation Biochemistry 42 2003 4084 4093
28. Y. Kim, S. Kim, T.N. Earnest and W.G. Hol Precursor structure of cephalosporin acylase. Insights into autoproteolytic activation in a new N-terminal hydrolase family J Biol Chem 277 2002 2823 2829 After the elucidation of the crystal structure of cephalosporin acylase and cephalosporin acylase complexed with glutaryl-7-ACA this is the first structure of a non-maturating variant of the enzyme, providing insight into the mechanism of autocatalytic processing of the precursor peptide.
29. J. Yoon, B. Oh, K. Kim, J. Park, D. Han, K.K. Kim, S.S. Cha, D. Lee and Y. Kim A bound water molecule is crucial in initiating autocatalytic precursor activation in an N-terminal hydrolase J Biol Chem 279 2004 341 347
30. T.R.M. Barends, J.J. Polderman-Tijmes, P.A. Jekel, C.M.H. Hensgens, E.J. de Vries, D.B. Janssen and B.W. Dijkstra The sequence and crystal structure of the α-amino acid ester hydrolase from Xanthomonas citri define a new family of β-lactam antibiotic acylases J Biol Chem 278 2003 23076 23084 The crystal structure of an α-amino acid ester hydrolase nicely shows how the α-amino group can be compensated for in the active site, explaining the substrate specificity of this class of enzymes.
31. J.J. Polderman-Tijmes, P.A. Jekel, E.J. de Vries, A.E.J. van Merode, R. Floris, J.M. van der Laan, T. Sonke and D.B. Janssen Cloning, sequence analysis, and expression in Escherichia coli of the gene encoding an α-amino acid ester hydrolase from Acetobacter turbidans Appl Environ Microbiol 68 2002 211 218
32. W.B.L. Alkema, E. de Vries, R. Floris and D.B. Janssen Kinetics of enzyme acylation and deacylation in the penicillin acylase-catalyzed synthesis of β-lactam antibiotics Eur J Biochem 270 2003 3675 3683
33. L.R.B. Goncalves, R. Sousa, R. Fernandez-Lafuente, J.M. Guisan, R.L.C. Giordano and R.C. Giordano Enzymatic synthesis of amoxicillin - avoiding limitations of the mechanistic approach for reaction kinetics Biotechnol Bioeng 80 2002 622 631
34. M.I. Youshko, G.G. Chilov, T.A. Shcherbakova and V.K. Svedas Quantitative characterization of the nucleophile reactivity in penicillin acylase-catalyzed acyl transfer reactions Biochim Biophys Acta 1599 2002 134 140
35. R.V. Ulijn, L. De Martin, P.J. Halling, B.D. Moore and A.E.M. Janssen Enzymatic synthesis of β-lactam antibiotics via direct condensation J Biotechnol 99 2002 215 222 Exploration of the use of ions to precipitate amoxicillin during the PGA-catalyzed synthesis reaction, thereby shifting the equilibrium of the reaction towards the product and increasing the antibiotic yield.
36. L.M. van Langen, N.H.P. Oosthoek, F. van Rantwijk and R.A. Sheldon Penicillin acylase catalysed synthesis of ampicillin in hydrophilic organic solvents Adv Synthesis Catalysis 345 2003 797 801
37. D.Z. Wei, J.H. Zhu and X.J. Cao Enzymatic synthesis of cephalexin in aqueous two-phase systems Biochem Eng J 11 2002 95 99
38. A. Illanes, Z. Cabrera, L. Wilson and C. Aguirre Synthesis of cephalexin in ethylene glycol with glyoxyl-agarose immobilised penicillin acylase: temperature and pH optimisation Process Biochem 39 2003 111 117
39. A. Basso, P. Braiuca, S. Clementi, C. Ebert, L. Gardossi and P. Linda Computational analysis of the aminic subsite of PGA explains the influence of amine structure on enantioselectivity J Mol Catal, B Enzym 19 2002 423 430 Using GRID analysis the substrate-binding site of PGA was 'mapped', this helped to explain the stereospecificity of the enzyme towards derivatives of several amino acids.
40. G.G. Chilov, H.M. Moody, W.H.J. Boesten and V.K. Svedas Resolution of (RS)-phenylglycinonitrile by penicillin acylase-catalyzed acylation in aqueous medium Tetrahedron Asymm 14 2003 2613 2617
41. B.H. Landis, P.B. Mullins, K.E. Mullins and P.T. Wang Kinetic resolution of β-amino esters by acylation using immobilized penicillin amidohydrolase Org Process Res Dev 6 2002 539 546 Describes the resolution of a racemic β-amino ester via stereospecific acylation by PGA with ee values of over 98%. The process was scaled up to 70L batches.
42. Y.M. Yao and J.J. Lalonde Unexpected enantioselectivity and activity of penicillin acylase in the resolution of methyl 2,2-dimethyl-1,3-dioxane-4- carboxylate J Mol Catal, B Enzym 22 2003 55 59
43. S. Raimondi, D. Monti, U.M. Pagnoni and S. Riva Glutaryl acylases: one-reaction enzymes or versatile enantioselective biocatalysts? Adv Synthesis Catalysis 345 2003 783 789
44. A. Zadrazil, R. Chmelikova and P. Hasal Continuous penicillin G hydrolysis in an electro-membrane reactor with immobilized penicillin G acylase Biotechnol Lett 25 2003 485 490
45. G. Massolini, E. Calleri, A. Lavecchia, F. Lolodice, D. Lubda, C. Temporini, G. Fracchiolla, P. Tortorella, E. Novellino and G. Caccialanza Enantioselective hydrolysis of some 2-aryloxyalkanoic acid methyl esters and isosteric analogues using a penicillin G acylase-based HPLC monolithic silica column Anal Chem 75 2003 535 542
46. M.I. Youshko and Svedas VK Penicillin acylase-catalyzed solid-state ampicillin synthesis Adv Synthesis Catalysis 344 2002 894 898