University of Groningen Mutants and homologs of cephalosporin … · 2016-03-05 · CD (1995)...

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University of Groningen Mutants and homologs of cephalosporin acylase Sio, Charles Frederik IMPORTANT NOTE: You are advised to consult the publisher's version (publisher's PDF) if you wish to cite from it. Please check the document version below. Document Version Publisher's PDF, also known as Version of record Publication date: 2004 Link to publication in University of Groningen/UMCG research database Citation for published version (APA): Sio, C. F. (2004). Mutants and homologs of cephalosporin acylase: for antibiotics and antibiosis. s.n. Copyright Other than for strictly personal use, it is not permitted to download or to forward/distribute the text or part of it without the consent of the author(s) and/or copyright holder(s), unless the work is under an open content license (like Creative Commons). Take-down policy If you believe that this document breaches copyright please contact us providing details, and we will remove access to the work immediately and investigate your claim. Downloaded from the University of Groningen/UMCG research database (Pure): http://www.rug.nl/research/portal. For technical reasons the number of authors shown on this cover page is limited to 10 maximum. Download date: 06-11-2020

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Page 1: University of Groningen Mutants and homologs of cephalosporin … · 2016-03-05 · CD (1995) Production of cephalosporin intermediates by feeding adipic acid to recombinant Penicillium

University of Groningen

Mutants and homologs of cephalosporin acylaseSio, Charles Frederik

IMPORTANT NOTE: You are advised to consult the publisher's version (publisher's PDF) if you wish to cite fromit. Please check the document version below.

Document VersionPublisher's PDF, also known as Version of record

Publication date:2004

Link to publication in University of Groningen/UMCG research database

Citation for published version (APA):Sio, C. F. (2004). Mutants and homologs of cephalosporin acylase: for antibiotics and antibiosis. s.n.

CopyrightOther than for strictly personal use, it is not permitted to download or to forward/distribute the text or part of it without the consent of theauthor(s) and/or copyright holder(s), unless the work is under an open content license (like Creative Commons).

Take-down policyIf you believe that this document breaches copyright please contact us providing details, and we will remove access to the work immediatelyand investigate your claim.

Downloaded from the University of Groningen/UMCG research database (Pure): http://www.rug.nl/research/portal. For technical reasons thenumber of authors shown on this cover page is limited to 10 maximum.

Download date: 06-11-2020

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References

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1. http://www.unica.it/~webcontu/brotzu/brotzuen.htm, accessed on May 14, 2004. 2. Chain, E, Florey, HW, Gardner, AD, Heatley, NG, Jennings, MA, Orr-Ewing, J, and Sanders,

AG (1940) Penicillin as a chemotherapeutic agent. Lancet, 236, 226-228. 3. Abraham, EP, Chain, E, Fletcher, CM, Gardner, AD, Heatley, NG, Jennings, MA, and Florey,

HW (1941) Further observations on penicillin. Lancet, 238, 177-189. 4. Fleming, A (1928) On the antibacterial action of cultures of a Penicillium, with special

reference to their use in the isolation of B. influenzae. The British Journal of Experimental Pathology, 10, 226-236.

5. http://www.unica.it/~webcontu/brotzu/brotzuen.pdf, accessed on May 14, 2004. 6. Newton, GGF and Abraham, EP (1955) Cephalosporin C, a new antibiotic containing

sulphur and D-alpha-aminoadipic acid. Nature, 175, 548-548. 7. Giesbrecht, P, Kersten, T, Maidhof, H, and Wecke, J (1998) Staphylococcal cell wall:

morphogenesis and fatal variations in the presence of penicillin. Microbiology and Molecular Biology Reviews, 62, 1371-1414.

8. Tomasz, A (1979) The mechanism of the irreversible antimicrobial effects of penicillins: how the beta-lactam antibiotics kill and lyse bacteria. Annual Review of Biochemistry, 33, 113-137.

9. Commissie Farmaceutische Hulp (2004) Farmacotherapeutisch Kompas. College voor Zorgverzekeringen, Diemen.

10. WINAp (2003) Informatorium Medicamentorum. KNMP, Den Haag. 11. Elander, RP (2003) Industrial production of β-lactam antibiotics. Applied Microbiology and

Biotechnology, 61, 385-392. 12. http://open.imshealth.com/webshop2/IMSinclude/i_article_20040317.asp, accessed on May

14, 2004. 13. Dancer, SJ (2001) The problem with cephalosporins. Journal of Antimicrobial

Chemotherapy, 48, 463-478. 14. Wegman, MA, Janssen, MHA, van Rantwijk, F, and Sheldon, RA (2001) Towards

biocatalytic synthesis of β-lactam antibiotics. Advanced Synthesis & Catalysis, 343, 559-576. 15. Bruggink, A, Roos, EC, and de Vroom, E (1998) Penicillin acylase in the industrial

production of beta-lactam antibiotics. Organic Process Research & Development, 2, 128-133. 16. Crawford, L, Stepan, AM, McAda, PC, Rambosek, JA, Conder, MJ, Vinci, VA, and Reeves,

CD (1995) Production of cephalosporin intermediates by feeding adipic acid to recombinant Penicillium chrysogenum strains expressing ring expansion activity. Biotechnology N. Y., 13, 58-62.

17. Adrio, JL and Demain, AL (2002) Improvements in the formation of cephalosporins from penicillin G and other penicillins by bioconversion. Organic Process Research & Development, 6, 427-433.

18. Sio, CF, Riemens, AM, van der Laan, JM, Verhaert, RMD, and Quax, WJ (2002) Directed evolution of a glutaryl acylase into an adipyl acylase. European Journal of Biochemistry, 269, 4495-4504.

19. Galan, B, Garcia, JL, and Prieto, MA (2004) The PaaX repressor, a link between penicillin G acylase and the phenylacetyl-coenzyme A catabolon of Escherichia coli W. Journal of Bacteriology, 186, 2215-2220.

20. Biffi, S, De Martin, L, Ebert, C, Gardossi, L, and Linda, P (2002) Glutaryl-7-ACA acylase catalyses the synthesis of amide bond in heterogeneous substrate mixtures. Journal of Molecular Catalysis B-Enzymatic, 19, 135-141.

21. Raimondi, S, Monti, D, Pagnoni, UM, and Riva, S (2003) Glutaryl acylases: One-reaction enzymes or versatile enantioselective biocatalysts? Advanced Synthesis & Catalysis, 345, 783-789.

Page 4: University of Groningen Mutants and homologs of cephalosporin … · 2016-03-05 · CD (1995) Production of cephalosporin intermediates by feeding adipic acid to recombinant Penicillium

References

121

22. Shibuya, Y, Matsumoto, K, and Fujii, T (1981) Isolation and properties of 7-β-(4-carboxybutanamido)cephalosporanic acid acylase-producing bacteria. Agricultural & Biological Chemistry, 45, 1561-1567.

23. Ichikawa, S, Murai, Y, Yamamoto, S, Shibuya, Y, Fujii, T, Komatsu, K, and Kodaira, R (1981) The isolation and properties of Pseudomonas mutants with an enhanced productivity of 7-β-(4-carboxybutanamido)-cephalosporanic acid acylase. Agricultural & Biological Chemistry, 45, 2225-2229.

24. Ichikawa, S, Shibuya, Y, Matsumoto, K, Fujii, T, Komatsu, K, and Kodaira, R (1981) Purification and properties of 7-β-(4-carboxybutanamido)cephalosporanic acid acylase produced by mutants derived from Pseudomonas. Agricultural & Biological Chemistry, 45, 2231-2236.

25. Matsuda, A and Komatsu, KI (1985) Molecular cloning and structure of the gene for 7-β-(4-carboxybutanamido)cephalosporanic acid acylase from a Pseudomonas strain. Journal of Bacteriology, 163, 1222-1228.

26. Ishii, Y, Saito, Y, Fujimura, T, Isogai, T, Kojo, H, Yamashita, M, Niwa, M, and Kohsaka, M (1994) A novel 7-β-(4-carboxybutanamido)-cephalosporanic acid acylase isolated from Pseudomonas strain C427 and its high-level production in Escherichia coli. Journal of Fermentation and Bioengineering, 77, 591-597.

27. Lee, YS, Yang, HC, and Park, SS (1996) Cloning and characterization of GL-7-ACA acylase gene from Pseudomonas sp. GK16. Journal of Microbiology and Biotechnology, 6, 375-380.

28. Li, Y, Jiang, W, Yang, Y, Zhao, G, and Wang, E (1998) Overproduction and purification of glutaryl 7-amino cephalosporanic acid acylase. Protein Expression & Purification, 12, 233-238.

29. Kim, DW, Kang, SM, and Yoon, KH (1999) Isolation of novel Pseudomonas diminuta KAC-1 strain producing glutaryl 7-aminocephalosporanic acid acylase. Journal of Microbiology, 37, 200-205.

30. Kim, DW and Yoon, KH (2001) Cloning and high expression of glutaryl 7-aminocephalosporanic acid acylase gene from Pseudomonas diminuta. Biotechnology Letters, 23, 1067-1071.

31. Matsuda, A, Matsuyama, K, Yamamoto, K, Ichikawa, S, and Komatsu, K (1987) Cloning and characterization of the genes for two distinct cephalosporin acylases from a Pseudomonas strain. Journal of Bacteriology, 169, 5815-5820.

32. Matsuda, A, Toma, K, and Komatsu, K (1987) Nucleotide sequences of the genes for two distinct cephalosporin acylases from a Pseudomonas strain. Journal of Bacteriology, 169, 5821-5826.

33. Ishiye, M and Niwa, M (1992) Nucleotide sequence and expression in Escherichia coli of the cephalosporin acylase gene of a Pseudomonas strain. Biochimica et Biophysica Acta, 1132, 233-239.

34. Aramori, I, Fukagawa, M, Tsumura, M, Iwami, M, Yokota, Y, Kojo, H, Kohsaka, M, Ueda, Y, and Imanaka, H (1991) Isolation of soil strains producing new cephalosporin acylases. Journal of Fermentation and Bioengineering, 72, 227-231.

35. Aramori, I, Fukagawa, M, Tsumura, M, Iwami, M, Ono, H, Kojo, H, Kohsaka, M, Ueda, Y, and Imanaka, H (1991) Cloning and nucleotide sequencing of a novel 7-β-(4-carboxybutanamido)cephalosporanic acid acylase gene of Bacillus laterosporus and its expression in Escherichia coli and Bacillus subtilis. Journal of Bacteriology, 173, 7848-7855.

36. Aramori, I, Fukagawa, M, Tsumura, M, Iwami, M, Isogai, T, Ono, H, Ishitani, Y, Kojo, H, Kohsaka, M, Ueda, Y, and Imanaka, H (1991) Cloning and nucleotide sequencing of new glutaryl 7-ACA and cephalosporin C acylase genes from Pseudomonas strains. Journal of Fermentation and Bioengineering, 72, 232-243.

Page 5: University of Groningen Mutants and homologs of cephalosporin … · 2016-03-05 · CD (1995) Production of cephalosporin intermediates by feeding adipic acid to recombinant Penicillium

122

37. Binder, R, Brown, J, and Romancik, G (1994) Biochemical characterization of a glutaryl-7-aminocephalosporanic acid acylase from Pseudomonas strain Bl072. Applied and Environmental Microbiology, 60, 1805-1809.

38. Binder, RG, Numata, K, Lowe, DA, Murakami, T, and Brown, JL (1993) Isolation and characterization of a Pseudomonas strain producing glutaryl-7-aminocephalosporanic acid acylase. Applied and Environmental Microbiology, 59, 3321-3326.

39. Zhang, QJ and Xu, WX (1993) Morphological, physiological and enzymatic characteristics of cephalosporin acylase producing Arthrobacter strain 45-8A. Archives of Microbiology, 159, 392-395.

40. Nikolov, A and Danielsson, B (1994) Enzymatic transformation of cephalosporin C to 7-aminocephalosporanic acid. 1. Cultivation of Pseudomonas syringae and partial purification and immobilization of 7-β-(4-carboxybutanamido) cephalosporanic acid acylase. Enzyme and Microbial Technology, 16, 1031-1036.

41. Sonawane, VC, Jolly, RS, and Vohra, RM (1996) Cephalosporin modification: An extracellular glutaryl-7-ACA acylase from Bacillus sp. Biotechnology Letters, 18, 965-968.

42. Ambedkar, SS, Deshpande, BS, and Shewale, JG (1997) Separation of cephalosporin C acylase and penicillin V acylase from Aeromonas ACY 95 by chemical treatment. Process Biochemistry, 32, 305-307.

43. Battistel, E, Bianchi, D, Bortolo, R, and Bonoldi, L (1998) Purification and stability of glutaryl-7-ACA acylase from Pseudomonas sp. Applied Biochemistry and Biotechnology, 69, 53-67.

44. Lee, YH, Chang, TS, Liu, HJ, and Chu, WS (1998) An acidic glutaryl-7-aminocephalosporanic acid acylase from Pseudomonas nitroreducens. Biotechnology & Applied Biochemistry, 28, 113-118.

45. Khang, YH and Yoo, BH (2000) Isolation and characterization of a novel soil strain, Pseudomonas cepacia BY21, with glutaryl-7-aminocephalosporanic acid acylase activity. Biotechnology Letters, 22, 317-320.

46. Franzosi, G, Battistel, E, Gagliardi, I, and Van der, GW (1995) Screening and characterization of microorganisms with glutaryl-7-ADCA acylase activity. Applied Microbiology and Biotechnology, 43, 508-513.

47. Zhu, S, Yang, Y, Zhao, G, and Jiang, W (2003) A rapid and specific method to screen environmental microorganisms for cephalosporin acylase activity. Journal of Microbiological Methods, 54, 131-135.

48. Lee, YS and Park, SS (1998) Two-step autocatalytic processing of the glutaryl 7- aminocephalosporanic acid acylase from Pseudomonas sp. strain GK16. Journal of Bacteriology, 180, 4576-4582.

49. Li, Y, Chen, J, Jiang, W, Mao, X, Zhao, G, and Wang, E (1999) In vivo post-translational processing and subunit reconstitution of cephalosporin acylase from Pseudomonas sp. 130. European Journal of Biochemistry, 262, 713-719.

50. Lee, YS, Kim, HW, and Park, SS (2000) The role of alpha-amino group of the N-terminal serine of β subunit for enzyme catalysis and autoproteolytic activation of glutaryl 7-aminocephalosporanic acid acylase. Journal of Biological Chemistry, 275, 39200-39206.

51. Kim, Y, Yoon, K, Khang, Y, Turley, S, and Hol, WG (2000) The 2.0 Å crystal structure of cephalosporin acylase. Structure, 8, 1059-1068.

52. Fritz-Wolf, K, Koller, KP, Lange, G, Liesum, A, Sauber, K, Schreuder, H, Aretz, W, and Kabsch, W (2002) Structure-based prediction of modifications in glutarylamidase to allow single-step enzymatic production of 7-aminocephalosporanic acid from cephalosporin C. Protein Science, 11, 92-103.

53. Kim, JK, Yang, IS, Rhee, S, Dauter, Z, Lee, YS, Park, SS, and Kim, KH (2003) Crystal structures of glutaryl 7-aminocephalosporanic acid acylase: Insight into autoproteolytic activation. Biochemistry, 42, 4084-4093.

Page 6: University of Groningen Mutants and homologs of cephalosporin … · 2016-03-05 · CD (1995) Production of cephalosporin intermediates by feeding adipic acid to recombinant Penicillium

References

123

54. Kim, Y, Kim, S, Earnest, TN, and Hol, WG (2002) Precursor structure of cephalosporin acylase. Insights into autoproteolytic activation in a new N-terminal hydrolase family. Journal of Biological Chemistry, 277, 2823-2829.

55. Yoon, J, Oh, B, Kim, K, Park, J, Han, D, Kim, KK, Cha, SS, Lee, D, and Kim, Y (2004) A bound water molecule is crucial in initiating autocatalytic precursor activation in an N-terminal hydrolase. Journal of Biological Chemistry, 279, 341-347.

56. Kinoshita, T, Tada, T, Saito, Y, Ishii, Y, Sato, A, and Murata, M (2000) Crystallization and preliminary X-ray analysis of cephalosporin C acylase from Pseudomonas sp. strain N176. Acta Crystallographica Section D: Biological Crystallography, 56, 458-459.

57. Duggleby, HJ, Tolley, SP, Hill, CP, Dodson, EJ, Dodson, G, and Moody, PC (1995) Penicillin acylase has a single amino acid catalytic centre. Nature, 373, 264-268.

58. Alkema, WBL, de Vries, E, Floris, R, and Janssen, DB (2003) Kinetics of enzyme acylation and deacylation in the penicillin acylase-catalyzed synthesis of beta-lactam antibiotics. European Journal of Biochemistry, 270, 3675-3683.

59. Kim, Y and Hol, WG (2001) Structure of cephalosporin acylase in complex with glutaryl-7-aminocephalosporanic acid and glutarate: insight into the basis of its substrate specificity. Chemistry & Biology, 8, 1253-1264.

60. Schroen, CGPH, VandeWiel, S, Kroon, PJ, deVroom, E, Janssen, AEM, and Tramper, J (2000) Equilibrium position, kinetics, and reactor concepts for the adipyl-7-ADCA-hydrolysis process. Biotechnology and Bioengineering, 70, 654-661.

61. Schroen, CGPH, Kroon, PJ, Vanderlaan, JM, Janssen, AEM, and Tramper, J (2002) Enhancement of enzymatic adipyl-7-ADCA hydrolysis. Biocatalysis and Biotransformation, 20, 369-375.

62. Schroen, CGPH, Nierstrasz, VA, Bosma, R, Kroon, PJ, Tjeerdsma, PS, deVroom, E, Van der Laan, JM, Moody, HM, Beeftink, HH, Janssen, AEM, and Tramper, J (2002) Integrated reactor concepts for the enzymatic kinetic synthesis of cephalexin. Biotechnology and Bioengineering, 80, 144-155.

63. Schroen, CGPH, Nierstrasz, VA, Bosma, R, Dijkstra, ZJ, VandeSandt, EJAX, Beeftink, HH, and Tramper, J (2002) Process design for enzymatic adipyl-7-ADCA hydrolysis. Biotechnology Progress, 18, 745-751.

64. Chen, MC, Chen, LL, Lee, YH, Wen, CY, and Chu, WS (1995) Screening and characterization of glutaryl-7-aminocephalosporanic acid acylase from Pseudomonas sp. Biotechnology Techniques, 9, 859-862.

65. Lau, RM, van Eupen, JTH, Schipper, D, Tesser, GI, Verweij, J, and de Vroom, E (2000) Synthesis of penicillin N and isopenicillin N. Tetrahedron, 56, 7601-7606.

66. Bouvrette, P and Ziomek, E (1992) Use of delta-(alpha-aminoadipoyl) chromogenic amides in screening for aminoadipoyl amidohydrolases. Analytical Biochemistry, 200, 315-320.

67. Lorenz, P and Schleper, C (2002) Metagenome - a challenging source of enzyme discovery. Journal of Molecular Catalysis B: Enzymatic, 19-20, 13-19.

68. Stemmer, WP (1994) Rapid evolution of a protein in vitro by DNA shuffling. Nature, 370, 389-391.

69. Fernandez-Gacio, A, Uguen, M, and Fastrez, J (2003) Phage display as a tool for the directed evolution of enzymes. Trends in Biotechnology, 21, 408-414.

70. Verhaert, RMD, Beekwilder, J, Olsthoorn, R, van Duin, J, and Quax, WJ (2002) Phage display selects for amylases with improved low pH starch-binding. Journal of Biotechnology, 96, 103-118.

71. Verhaert, RMD, van Duin, J, and Quax, WJ (1999) Processing and functional display of the 86 kDa heterodimeric penicillin G acylase on the surface of phage fd. Biochemical Journal, 342, 415-422.

72. Bornscheuer, UT and Pohl, M (2001) Improved biocatalysts by directed evolution and rational protein design. Current Opinion in Chemical Biology, 5, 137-143.

Page 7: University of Groningen Mutants and homologs of cephalosporin … · 2016-03-05 · CD (1995) Production of cephalosporin intermediates by feeding adipic acid to recombinant Penicillium

124

73. Hult, K and Berglund, P (2003) Engineered enzymes for improved organic synthesis. Current Opinion in Biotechnology, 14, 395-400.

74. Kazlauskas, RJ (2000) Molecular modeling and biocatalysis: explanations, predictions, limitations, and opportunities. Current Opinion in Chemical Biology, 4, 81-88.

75. Bolon, DN, Voigt, CA, and Mayo, SL (2002) De novo design of biocatalysts. Current Opinion in Chemical Biology, 6, 125-129.

76. Fleischmann, RD, Adams, MD, White, O, Clayton, RA, Kirkness, EF, Kerlavage, AR, Bult, CJ, Tomb, JF, Dougherty, BA, Merrick, JM, McKenney, K, Sutton, G, Fitzhugh, W, Fields, C, Gocayne, JD, Scott, J, Shirley, R, Liu, LI, Glodek, A, Kelley, JM, Weidman, JF, Phillips, CA, Spriggs, T, Hedblom, E, Cotton, MD, Utterback, TR, Hanna, MC, Nguyen, DT, Saudek, DM, Brandon, RC, Fine, LD, Fritchman, JL, Fuhrmann, JL, Geoghagen, NSM, Gnehm, CL, Mcdonald, LA, Small, KV, Fraser, CM, Smith, HO, and Venter, JC (1995) Whole genome random sequencing and assembly of Haemophilus influenzae Rd. Science, 269, 496-512.

77. Bull, AT, Ward, AC, and Goodfellow, M (2000) Search and discovery strategies for biotechnology: The paradigm shift. Microbiology and Molecular Biology Reviews, 64, 573-606.

78. Altschul, SF, Madden, TL, Schaffer, AA, Zhang, J, Zhang, Z, Miller, W, and Lipman, DJ (1997) Gapped BLAST and PSI-BLAST: a new generation of protein database search programs. Nucleic Acids Research, 25, 3389-3402.

79. Lin, YH, Xu, JL, Hu, JY, Wang, LH, Ong, SL, Leadbetter, JR, and Zhang, LH (2003) Acyl-homoserine lactone acylase from Ralstonia strain XJ12B represents a novel and potent class of quorum-quenching enzymes. Molecular Microbiology, 47, 849-860.

80. Forney, LJ, Wong, DC, and Ferber, DM (1989) Selection of amidases with novel substrate specificities from penicillin amidase of Escherichia coli. Applied and Environmental Microbiology, 55, 2550-2555.

81. Morillas, M, McVey, CE, Brannigan, JA, Ladurner, AG, Forney, LJ, and Virden, R (2003) Mutations of penicillin acylase residue B71 extend substrate specificity by decreasing steric constraints for substrate binding. Biochemical Journal, 371, 143-150.

82. Ishii, Y, Saito, Y, Fujimura, T, Sasaki, H, Noguchi, Y, Yamada, H, Niwa, M, and Shimomura, K (1995) High-level production, chemical modification and site-directed mutagenesis of a cephalosporin C acylase from Pseudomonas strain N176. European Journal of Biochemistry, 230, 773-778.

83. Saito, Y, Ishii, Y, Fujimura, T, Sasaki, H, Noguchi, Y, Yamada, H, Niwa, M, and Shimomura, K (1996) Protein engineering of a cephalosporin C acylase from Pseudomonas strain N176. Annals of the New York Academy of Sciences, 782, 226-240.

84. Yamada, H, Ishii, Y, Noguchi, Y, Miura, T, Mori, T, and Saito, Y (1996) Protein engineering of a cephalosporin C acylase. Annals of the New York Academy of Sciences, 799, 74-81.

85. Saito, Y, Fujimura, T, Ishii, Y, Noguchi, Y, Miura, T, Niwa, M, and Shimomura, K (1996) Oxidative modification of a cephalosporin C acylase from Pseudomonas strain N176 and site-directed mutagenesis of the gene. Applied and Environmental Microbiology, 62, 2919-2925.

86. Oh, B, Kim, M, Yoon, J, Chung, K, Shin, Y, Lee, D, and Kim, Y (2003) Deacylation activity of cephalosporin acylase to cephalosporin C is improved by changing the side-chain conformations of active-site residues. Biochemical and Biophysical Research Communications, 310, 19-27.

87. Arroyo, M, de la Mata, I, Acebal, C, and Pilar, CM (2003) Biotechnological applications of penicillin acylases: state-of-the-art. Applied Microbiology and Biotechnology, 60, 507-514.

88. Plhackova, K, Becka, S, Skrob, F, and Kyslik, P (2003) Isolation and characterization of a new strain of Achromobacter sp with beta-lactam antibiotic acylase activity. Applied Microbiology and Biotechnology, 62, 507-516.

Page 8: University of Groningen Mutants and homologs of cephalosporin … · 2016-03-05 · CD (1995) Production of cephalosporin intermediates by feeding adipic acid to recombinant Penicillium

References

125

89. Skrob, F, Becka, S, Plhackova, K, Fotopulosova, V, and Kyslik, P (2003) Novel penicillin G acylase from Achromobacter sp CCM 4824. Enzyme and Microbial Technology, 32, 738-744.

90. Torres-Guzman, R, De la Mata, I, Torres-Bacete, J, Arroyo, M, Castillon, MP, and Acebal, C (2002) Substrate specificity of penicillin acylase from Streptomyces lavendulae. Biochemical and Biophysical Research Communications, 291, 593-597.

91. Polderman-Tijmes, JJ, Jekel, PA, de Vries, EJ, van Merode, AE, Floris, R, Der Laan, JM, Sonke, T, and Janssen, DB (2002) Cloning, sequence analysis, and expression in Escherichia coli of the gene encoding an alpha-amino acid ester hydrolase from Acetobacter turbidans. Applied and Environmental Microbiology, 68, 211-218.

92. Polderman-Tijmes, JJ, Jekel, PA, Jeronimus-Stratingh, CM, Bruins, AP, van der Laan, JM, Sonke, T, and Janssen, DB (2002) Identification of the catalytic residues of alpha-amino acid ester hydrolase from Acetobacter turbidans by labeling and site-directed mutagenesis. Journal of Biological Chemistry, 277, 28474-28482.

93. Takahashi, T, Yamazaki, Y, Kato, K, and Isono, M (1972) Enzymatic synthesis of cephalosporins. Journal of the American Chemical Society, 94, 4035-4038.

94. Yang, S, Zhou, LP, Tang, HX, Pan, J, Wu, XJ, Huang, H, and Yuan, ZY (2002) Rational design of a more stable penicillin G acylase against organic cosolvent. Journal of Molecular Catalysis B-Enzymatic, 18, 285-290.

95. Abian, O, Grazu, V, Hermoso, J, Gonzalez, R, Garcia, JL, Fernandez-Lafuente, R, and Guisan, JM (2004) Stabilization of penicillin G acylase from Escherichia coli: Site-directed mutagenesis of the protein surface to increase multipoint covalent attachment. Applied and Environmental Microbiology, 70, 1249-1251.

96. Alkema, WBL, Dijkhuis, AJ, de Vries, E, and Janssen, DB (2002) The role of hydrophobic active-site residues in substrate specificity and acyl transfer activity of penicillin acylase. European Journal of Biochemistry, 269, 2093-2100.

97. Zhou, Z, Zhang, AH, Wang, JR, Chen, ML, Li, RB, Yang, S, and Yuan, ZY (2003) Improving the specific synthetic activity of a penicillin G acylase using DNA family shuffling. Acta Biochimica et Biophysica Sinica, 35, 573-579.

98. Otten, LG, Sio, CF, Vrielink, J, Cool, RH, and Quax, WJ (2002) Altering the substrate specificity of cephalosporin acylase by directed evolution of the β-subunit. Journal of Biological Chemistry, 277, 42121-42127.

99. Sio, CF, Otten, LG, Cool, RH, and Quax, WJ (2003) Analysis of a substrate specificity switch residue of cephalosporin acylase. Biochemical and Biophysical Research Communications, 312, 755-760.

100. Otten, LG, Sio, CF, Sloot, AM van der, Cool, RH, and Quax, WJ (2004) Mutational analysis of a key residue in the substrate specificity of a cephalosporin acylase. ChemBioChem, 5, 820-825.

101. Huang, X, Zeng, R, Ding, X, Mao, X, Ding, Y, Rao, Z, Xie, Y, Jiang, W, and Zhao, G (2002) Affinity alkylation of the Trp-B4 residue of the β-subunit of the glutaryl 7-aminocephalosporanic acid acylase of Pseudomonas sp. 130. Journal of Biological Chemistry, 277, 10256-10264.

102. Zhang, W, Huang, X, Zhao, G, and Jiang, W (2004) Affinity labeled glutaryl-7-amino cephalosporanic acid acylase C130 can hydrolyze the inhibitor during crystallization. Biochemical and Biophysical Research Communications, 313, 555-558.

103. Barends, TRM, Polderman-Tijmes, JJ, Jekel, PA, Hensgens, CMH, de Vries, EJ, Janssen, DB, and Dijkstra, BW (2003) The sequence and crystal structure of the alpha-amino acid ester hydrolase from Xanthomonas citri define a new family of beta-lactam antibiotic acylases. Journal of Biological Chemistry, 278, 23076-23084.

104. Goncalves, LRB, Sousa, R, Fernandez-Lafuente, R, Guisan, JM, Giordano, RLC, and Giordano, RC (2002) Enzymatic synthesis of amoxicillin - Avoiding limitations of the mechanistic approach for reaction kinetics. Biotechnology and Bioengineering, 80, 622-631.

Page 9: University of Groningen Mutants and homologs of cephalosporin … · 2016-03-05 · CD (1995) Production of cephalosporin intermediates by feeding adipic acid to recombinant Penicillium

126

105. Youshko, MI, Chilov, GG, Shcherbakova, TA, and Svedas, VK (2002) Quantitative characterization of the nucleophile reactivity in penicillin acylase-catalyzed acyl transfer reactions. Biochimica et Biophysica Acta-Proteins and Proteomics, 1599, 134-140.

106. Ulijn, RV, De Martin, L, Halling, PJ, Moore, BD, and Janssen, AEM (2002) Enzymatic synthesis of beta-lactam antibiotics via direct condensation. Journal of Biotechnology, 99, 215-222.

107. Van Langen, LM, Oosthoek, NHP, van Rantwijk, F, and Sheldon, RA (2003) Penicillin acylase catalysed synthesis of ampicillin in hydrophilic organic solvents. Advanced Synthesis & Catalysis, 345, 797-801.

108. Wei, DZ, Zhu, JH, and Cao, XJ (2002) Enzymatic synthesis of cephalexin in aqueous two-phase systems. Biochemical Engineering Journal, 11, 95-99.

109. Illanes, A, Cabrera, Z, Wilson, L, and Aguirre, C (2003) Synthesis of cephalexin in ethylene glycol with glyoxyl-agarose immobilised penicillin acylase: temperature and pH optimisation. Process Biochemistry, 39, 111-117.

110. Basso, A, Braiuca, P, Clementi, S, Ebert, C, Gardossi, L, and Linda, P (2002) Computational analysis of the aminic subsite of PGA explains the influence of amine structure on enantioselectivity. Journal of Molecular Catalysis B-Enzymatic, 19, 423-430.

111. Chilov, GG, Moody, HM, Boesten, WHJ, and Svedas, VK (2003) Resolution of (RS)-phenylglycinonitrile by penicillin acylase-catalyzed acylation in aqueous medium. Tetrahedron-Asymmetry, 14, 2613-2617.

112. Landis, BH, Mullins, PB, Mullins, KE, and Wang, PT (2002) Kinetic resolution of beta-amino esters by acylation using immobilized penicillin amidohydrolase. Organic Process Research & Development, 6, 539-546.

113. Yao, YM and Lalonde, JJ (2003) Unexpected enantioselectivity and activity of penicillin acylase in the resolution of methyl 2,2-dimethyl-1,3-dioxane-4- carboxylate. Journal of Molecular Catalysis B-Enzymatic, 22, 55-59.

114. Zadrazil, A, Chmelikova, R, and Hasal, P (2003) Continuous penicillin G hydrolysis in an electro-membrane reactor with immobilized penicillin G acylase. Biotechnology Letters, 25, 485-490.

115. Massolini, G, Calleri, E, Lavecchia, A, Loiodice, F, Lubda, D, Temporini, C, Fracchiolla, G, Tortorella, P, Novellino, E, and Caccialanza, G (2003) Enantioselective hydrolysis of some 2-aryloxyalkanoic acid methyl esters and isosteric analogues using a penicillin G acylase-based HPLC monolithic silica column. Analytical Chemistry, 75, 535-542.

116. Youshko, MI and Svedas, VK (2002) Penicillin acylase-catalyzed solid-state ampicillin synthesis. Advanced Synthesis & Catalysis, 344, 894-898.

117. IMS Health Global Services (2001) Pharmaceutical World Review 2000. 118. Xie, Y, Van de Sandt, E, de Weerd, T, and Wang, NH (2001) Purification of adipoyl-7-

amino-3-deacetoxycephalosporanic acid from fermentation broth using stepwise elution with a synergistically adsorbed modulator. Journal of Chromatography A, 908, 273-291.

119. Deshpande, BS, Ambedkar, SS, Sudhakaran, VK, and Shewale, JG (1994) Molecular biology of beta-lactam acylases. World Journal of Microbiology and Biotechnology, 10, 129-138.

120. McDonough, MA, Klei, HE, and Kelly, JA (1999) Crystal structure of penicillin G acylase from the Bro1 mutant strain of Providencia rettgeri. Protein Science, 8, 1971-1981.

121. Nilsson, B, Uhlen, M, Josephson, S, Gatenbeck, S, and Philipson, L (1983) An improved positive selection plasmid vector constructed by oligonucleotide mediated mutagenesis. Nucleic Acids Research, 11, 8019-8030.

122. Stanssens, P, Opsomer, C, McKeown, YM, Kramer, W, Zabeau, M, and Fritz, HJ (1989) Efficient oligonucleotide-directed construction of mutations in expression vectors by the gapped duplex DNA method using alternating selectable markers. Nucleic Acids Research, 17, 4441-4454.

Page 10: University of Groningen Mutants and homologs of cephalosporin … · 2016-03-05 · CD (1995) Production of cephalosporin intermediates by feeding adipic acid to recombinant Penicillium

References

127

123. De Boer, HA, Comstock, LJ, and Vasser, M (1983) The tac promoter: a functional hybrid derived from the trp and lac promoters. Proceedings of the National Academy of Sciences of the United States of America, 80, 21-25.

124. Murray, V (1989) Improved double-stranded DNA sequencing using the linear polymerase chain reaction. Nucleic Acids Research, 17, 8889.

125. Hermes, JD, Parekh, SM, Blacklow, SC, Koster, H, and Knowles, JR (1989) A reliable method for random mutagenesis: the generation of mutant libraries using spiked oligodeoxyribonucleotide primers. Gene, 84, 143-151.

126. Garcia, JL and Buesa, JM (1986) An improved method to clone penicillin acylase genes: Cloning and expression in Escherichia coli of penicillin G acylase from Kluyvera citrophila. Journal of Biotechnology, 3, 187-195.

127. Sambrook, J, Fritsch, EF, and Maniatis, T (1989) Molecular cloning: a laboratory manual, 2nd edition. Cold Spring Harbor Laboratory Press, Cold Spring Harbor, New York.

128. Udenfriend, S, Stein, S, Bohlen, P, Dairman, W, Leimgruber, W, and Weigele, M (1972) Fluorescamine: a reagent for assay of amino acids, peptides, proteins, and primary amines in the picomole range. Science, 178, 871-872.

129. Reyes, F, Martinez, MJ, and Soliveri, J (1989) Determination of cephalosporin C amidohydrolase activity with fluorescamine. Journal of Pharmacy & Pharmacology, 41, 136-137.

130. Nielsen, H, Engelbrecht, J, Brunak, S, and von Heijne, G (1997) Identification of prokaryotic and eukaryotic signal peptides and prediction of their cleavage sites. Protein Engineering, 10, 1-6.

131. Tjalsma, H, Bolhuis, A, Jongbloed, JD, Bron, S, and van Dijl, JM (2000) Signal peptide-dependent protein transport in Bacillus subtilis: a genome-based survey of the secretome. Microbiology and Molecular Biology Reviews, 64, 515-547.

132. Daumy, GO, Danley, D, and McColl, AS (1985) Role of protein subunits in Proteus rettgeri penicillin G acylase. Journal of Bacteriology, 163, 1279-1281.

133. Martin, J, Prieto, I, Barbero, JL, Perez-Gil, J, Mancheno, JM, and Arche, R (1990) Thermodynamic profiles of penicillin G hydrolysis catalyzed by wild-type and Met-Ala168 mutant penicillin acylases from Kluyvera citrophila. Biochimica et Biophysica Acta, 1037, 133-139.

134. Sizmann, D, Keilmann, C, and Bock, A (1990) Primary structure requirements for the maturation in vivo of penicillin acylase from Escherichia coli ATCC 11105. European Journal of Biochemistry, 192, 143-151.

135. Kim, S and Kim, Y (2001) Active site residues of cephalosporin acylase are critical not only for enzymatic catalysis but also for post-translational modification. Journal of Biological Chemistry, 276, 48376-48381.

136. Roa, A, Garcia, JL, Salto, F, and Cortes, E (1994) Changing the substrate specificity of penicillin G acylase from Kluyvera citrophila through selective pressure. Biochemical Journal, 303, 869-875.

137. Alkema, WB, Hensgens, CM, Kroezinga, EH, de Vries, E, Floris, R, van der Laan, JM, Dijkstra, BW, and Janssen, DB (2000) Characterization of the beta-lactam binding site of penicillin acylase of Escherichia coli by structural and site-directed mutagenesis studies. Protein Engineering, 13, 857-863.

138. McVey, CE, Walsh, MA, Dodson, GG, Wilson, KS, and Brannigan, JA (2001) Crystal structures of penicillin acylase enzyme-substrate complexes: structural insights into the catalytic mechanism. Journal of Molecular Biology, 313, 139-150.

139. Done, SH, Brannigan, JA, Moody, PC, and Hubbard, RE (1998) Ligand-induced conformational change in penicillin acylase. Journal of Molecular Biology, 284, 463-475.

Page 11: University of Groningen Mutants and homologs of cephalosporin … · 2016-03-05 · CD (1995) Production of cephalosporin intermediates by feeding adipic acid to recombinant Penicillium

128

140. Hagler, AT (1985) Theoretical simulation of conformation, energetics, and dynamics of peptides. In Conformation in Biology and Drug Design, the Peptides, edited by Meienhofer, J. Academic Press, New York, 213-299.

141. Armisen, P, Mateo, C, Cortes, E, Barredo, JL, Salto, F, Diez, B, Rodes, L, Garcia, JL, Fernandez-Lafuente, R, and Guisan, JM (1999) Selective adsorption of poly-His tagged glutaryl acylase on tailor-made metal chelate supports. Journal of Chromatography A, 848, 61-70.

142. Arnold, FH, Wintrode, PL, Miyazaki, K, and Gershenson, A (2001) How enzymes adapt: lessons from directed evolution. Trends in Biochemical Sciences, 26, 100-106.

143. Zhao, HM, Chockalingam, K, and Chen, ZL (2002) Directed evolution of enzymes and pathways for industrial biocatalysis. Current Opinion in Biotechnology, 13, 104-110.

144. Monti, D, Carrea, G, Riva, S, Baldaro, E, and Frare, G (2000) Characterization of an industrial biocatalyst: Immobilized glutaryl-7-ACA acylase. Biotechnology and Bioengineering, 70, 239-244.

145. Leung, DW, Chen, E, and Goeddel, DV (2004) A method for random mutagenesis of a defined DNA segment using a modified polymerase chain reaction. Technique, 1, 11-15.

146. Laemmli, UK (1970) Cleavage of structural proteins during the assembly of the head of bacteriophage T4. Nature, 227, 680-685.

147. Cadwell, RC and Joyce, GF (1994) Mutagenic PCR. PCR Methods and Applications, 3, S136-S140.

148. Griffiths, AD and Tawfik, DS (2000) Man-made enzymes - from design to in vitro compartmentalisation. Current Opinion in Biotechnology, 11, 338-353.

149. Forney, LJ and Wong, DC (1989) Alteration of the catalytic efficiency of penicillin amidase from Escherichia coli. Applied and Environmental Microbiology, 55, 2556-2560.

150. Landt, O, Grunert, HP, and Hahn, U (1990) A general method for rapid site-directed mutagenesis using the polymerase chain reaction. Gene, 96, 125-128.

151. Alkema, WB, Floris, R, and Janssen, DB (1999) The use of chromogenic reference substrates for the kinetic analysis of penicillin acylases. Analytical Biochemistry, 275, 47-53.

152. de Kievit, TR and Iglewski, BH (2000) Bacterial quorum sensing in pathogenic relationships. Infection and Immunity, 68, 4839-4849.

153. Latifi, A, Foglino, M, Tanaka, K, Williams, P, and Lazdunski, A (1996) A hierarchical quorum-sensing cascade in Pseudomonas aeruginosa links the transcriptional activators LasR and RhlR (VsmR) to expression of the stationary-phase sigma factor RpoS. Molecular Microbiology, 21, 1137-1146.

154. Whitehead, NA, Barnard, AML, Slater, H, Simpson, NJL, and Salmond, GPC (2001) Quorum-sensing in Gram-negative bacteria. FEMS Microbiology Reviews, 25, 365-404.

155. Parsek, MR and Greenberg, EP (2000) Acyl-homoserine lactone quorum sensing in Gram-negative bacteria: A signaling mechanism involved in associations with higher organisms. Proceedings of the National Academy of Sciences of the United States of America, 97, 8789-8793.

156. Dong, YH, Xu, JL, Li, XZ, and Zhang, LH (2000) AiiA, an enzyme that inactivates the acylhomoserine lactone quorum-sensing signal and attenuates the virulence of Erwinia carotovora. Proceedings of the National Academy of Sciences of the United States of America, 97, 3526-3531.

157. Williams, P (2002) Quorum sensing: an emerging target for antibacterial chemotherapy? Expert Opinion on Therapeutic Targets, 6, 257-274.

158. Hentzer, M, Wu, H, Andersen, JB, Riedel, K, Rasmussen, TB, Bagge, N, Kumar, N, Schembri, MA, Song, ZJ, Kristoffersen, P, Manefield, M, Costerton, JW, Molin, S, Eberl, L, Steinberg, P, Kjelleberg, S, Hoiby, N, and Givskov, M (2003) Attenuation of Pseudomonas aeruginosa virulence by quorum sensing inhibitors. EMBO Journal, 22, 3803-3815.

Page 12: University of Groningen Mutants and homologs of cephalosporin … · 2016-03-05 · CD (1995) Production of cephalosporin intermediates by feeding adipic acid to recombinant Penicillium

References

129

159. Leadbetter, JR and Greenberg, EP (2000) Metabolism of acyl-homoserine lactone quorum-sensing signals by Variovorax paradoxus. Journal of Bacteriology, 182, 6921-6926.

160. Huang, JJ, Han, JI, Zhang, LH, and Leadbetter, JR (2003) Utilization of acyl-homoserine lactone quorum signals for growth by a soil pseudomonad and Pseudomonas aeruginosa PAO1. Applied and Environmental Microbiology, 69, 5941-5949.

161. Stover, CK, Pham, XQ, Erwin, AL, Mizoguchi, SD, Warrener, P, Hickey, MJ, Brinkman, FS, Hufnagle, WO, Kowalik, DJ, Lagrou, M, Garber, RL, Goltry, L, Tolentino, E, Westbrock-Wadman, S, Yuan, Y, Brody, LL, Coulter, SN, Folger, KR, Kas, A, Larbig, K, Lim, R, Smith, K, Spencer, D, Wong, GK, Wu, Z, and Paulsen, IT (2000) Complete genome sequence of Pseudomonas aeruginosa PA01, an opportunistic pathogen. Nature, 406, 959-964.

162. Whiteley, M, Lee, KM, and Greenberg, EP (1999) Identification of genes controlled by quorum sensing in Pseudomonas aeruginosa. Proceedings of the National Academy of Sciences of the United States of America, 96, 13904-13909.

163. Lamont, IL and Martin, LW (2003) Identification and characterization of novel pyoverdine synthesis genes in Pseudomonas aeruginosa. Microbiology, 149, 833-842.

164. Chhabra, SR, Stead, P, Bainton, NJ, Salmond, GPC, Stewart, GSAB, Williams, P, and Bycroft, BW (1993) Autoregulation of carbapenem biosynthesis in Erwinia carotovora by analogs of N-(3-oxohexanoyl)-L-homoserine lactone. Journal of Antibiotics, 46, 441-454.

165. Pesci, EC, Milbank, JBJ, Pearson, JP, McKnight, S, Kende, AS, Greenberg, EP, and Iglewski, BH (1999) Quinolone signaling in the cell-to-cell communication system of Pseudomonas aeruginosa. Proceedings of the National Academy of Sciences of the United States of America, 96, 11229-11234.

166. Diggle, SP, Winzer, K, Chhabra, SR, Chhabra, SR, Worrall, KE, Cámara, M, and Williams, P (2003) The Pseudomonas aeruginosa quinolone signal molecule overcomes the cell density-dependency of the quorum sensing hierarchy, regulates rhl-dependent genes at the onset of stationary phase and can be produced in the absence of LasR. Molecular Microbiology, 50, 29-43.

167. Chen, WP and Kuo, TT (1993) A simple and rapid method for the preparation of Gram-negative bacterial genomic DNA. Nucleic Acids Research, 21, 2260.

168. Heeb, S, Blumer, C, and Haas, D (2002) Regulatory RNA as mediator in GacA/RsmA-dependent global control of exoproduct formation in Pseudomonas fluorescens CHA0. Journal of Bacteriology, 184, 1046-1056.

169. McClean, KH, Winson, MK, Fish, L, Taylor, A, Chhabra, SR, Cámara, M, Daykin, M, Lamb, JH, Swift, S, Bycroft, BW, Stewart, GSAB, and Williams, P (1997) Quorum sensing and Chromobacterium violaceum: exploitation of violacein production and inhibition for the detection of N-acylhomoserine lactones. Microbiology, 143, 3703-3711.

170. Winson, MK, Swift, S, Fish, L, Throup, JP, Jørgensen, F, Chhabra, SR, Bycroft, BW, Williams, P, and Stewart, GSAB (1998) Construction and analysis of luxCDABE-based plasmid sensors for investigating N-acyl homoserine lactone-mediated quorum sensing. FEMS Microbiology Letters, 163, 185-192.

171. Swift, S, Karlyshev, AV, Fish, L, Durant, EL, Winson, MK, Chhabra, SR, Williams, P, MacIntyre, S, and Stewart, GSAB (1997) Quorum sensing in Aeromonas hydrophila and Aeromonas salmonicida: Identification of the LuxRI homologs AhyRI and AsaRI and their cognate N-acylhomoserine lactone signal molecules. Journal of Bacteriology, 179, 5271-5281.

172. Winzer, K, Falconer, C, Garber, NC, Diggle, SP, Cámara, M, and Williams, P (2000) The Pseudomonas aeruginosa lectins PA-IL and PA-IIL are controlled by quorum sensing and by RpoS. Journal of Bacteriology, 182, 6401-6411.

173. Smith, AW and Iglewski, BH (1989) Transformation of Pseudomonas aeruginosa by electroporation. Nucleic Acids Research, 17, 10509-10509.

Page 13: University of Groningen Mutants and homologs of cephalosporin … · 2016-03-05 · CD (1995) Production of cephalosporin intermediates by feeding adipic acid to recombinant Penicillium

130

174. Ohman, DE, Cryz, SJ, and Iglewski, BH (1980) Isolation and characterization of a Pseudomonas aeruginosa PAO mutant that produces altered elastase. Journal of Bacteriology, 142, 836-842.

175. Essar, DW, Eberly, L, Hadero, A, and Crawford, IP (1990) Identification and characterization of genes for a second anthranilate synthase in Pseudomonas aeruginosa: interchangeability of the two anthranilate synthases and evolutionary implications. Journal of Bacteriology, 172, 884-900.

176. Wagner, VE, Bushnell, D, Passador, L, Brooks, AI, and Iglewski, BH (2003) Microarray analysis of Pseudomonas aeruginosa quorum-sensing regulons: Effects of growth phase and environment. Journal of Bacteriology, 185, 2080-2095.

177. Schuster, M, Lostroh, CP, Ogi, T, and Greenberg, EP (2003) Identification, timing, and signal specificity of Pseudomonas aeruginosa quorum-controlled genes: a transcriptome analysis. Journal of Bacteriology, 185, 2066-2079.

178. Déziel, E, Lépine, F, Milot, S, He, JX, Mindrinos, MN, Tompkins, RG, and Rahme, LG (2004) Analysis of Pseudomonas aeruginosa 4-hydroxy-2-alkylquinolines (HAQs) reveals a role for 4-hydroxy-2-heptylquinoline in cell-to-cell communication. Proceedings of the National Academy of Sciences of the United States of America, 101, 1339-1344.

179. Ochsner, UA, Wilderman, PJ, Vasil, AI, and Vasil, ML (2002) GeneChipR expression analysis of the iron starvation response in Pseudomonas aeruginosa: identification of novel pyoverdine biosynthesis genes. Molecular Microbiology, 45, 1277-1287.

180. Singh, PK, Parsek, MR, Greenberg, EP, and Welsh, MJ (2002) A component of innate immunity prevents bacterial biofilm development. Nature, 417, 552-555.

181. Zhang, H-B, Wang, C, and Zhang, LH (2004) The quormone degradation system of Agrobacterium tumefaciens is regulated by starvation signal and stress hormone (p)ppGpp. Molecular Microbiology, 52, 1389-1401.

182. Quax, WJ (2003) Bacterial enzymes. In The prokaryotes: an evolving electronic resource for the microbiological community, edited by Dworkin, M. Springer Verlag, New York.

183. Otten, LG (2004) Directed evolution of a cephalosporin acylase. Ph. D. thesis, University of Groningen.

184. Kreuzman, AJ, Hodges, RL, Swartling, JR, Pohl, TE, Ghag, SK, Baker, PJ, McGilvray, D, Yeh, WK (2000) Membrane-associated echinocandin B deacylase of Actinoplanes utahensis: purification, characterization, heterologous cloning and enzymatic deacylation reaction. Journal of Industrial Microbiology & Biotechnology, 24, 173-180.

185. Crameri, A, Raillard, SA, Bermudez, E, Stemmer, WPC (1998) DNA shuffling of a family of genesfrom diverse species accelerates directed evolution. Nature, 391, 288-291.