Enzymatic modifications of cephalosporins by cephalosporin acylase and other enzymes

Critical Reviews in Biotechnology

Volumn 26, Issue 2, 2006, Pages 95-120

  Sonawane, Vijay ^a  

^a INSTITUTE OF MICROBIAL TECHNOLOGY   (India)

Author keywords

7 ACA; Acylase; Biotransformations; Cephalosporin C; D amino acid oxidase; Esterase

Indexed keywords

AMINO ACIDS; BACTERIA; CELL IMMOBILIZATION; CLONING; GENES; MOLECULAR BIOLOGY; ORGANIC ACIDS;

7-ACA; ACYLASE; BIOTRANSFORMATIONS; CEPHALOSPORIN C; D-AMINO ACID OXIDASE; ESTERASE;

ENZYME KINETICS;

7 AMINOCEPHALOSPORANIC ACID; AMIDASE; BETA LACTAMASE; CARBON; CEPHALOSPORIN ACETYLESTERASE; CEPHALOSPORIN ACYLASE; CEPHALOSPORIN C; CEPHALOSPORIN C ACYLASE; CEPHALOSPORIN DERIVATIVE; CEPHAMYCIN; DEXTRO AMINO ACID OXIDASE; ESTERASE; GLUTARYL 7 AMINOCEPHALOSPORANIC ACID ACYLASE; NITROGEN; PENICILLIN ACYLASE; UNCLASSIFIED DRUG;

ACETOBACTER; ACREMONIUM; AEROMONAS; ANTIBIOTIC BIOSYNTHESIS; ARTHROBACTER; BACILLUS; BACTERIUM CULTURE; BIOCATALYST; BIOTRANSFORMATION; CEPHALOSPORIUM ACREMONIUM; CHEMICAL MODIFICATION; DEACETYLATION; DEAMINATION; DRUG STRUCTURE; ENZYME IMMOBILIZATION; ENZYME ISOLATION; ENZYME PURIFICATION; FLAVOBACTERIUM; GENE EXPRESSION; GENE STRUCTURE; GENETIC ENGINEERING; MOLECULAR CLONING; NOCARDIA; NONHUMAN; PRIORITY JOURNAL; PROTEIN ENGINEERING; PROTEIN PROCESSING; PSEUDOMONAS; REVIEW; SEQUENCE HOMOLOGY; STREPTOMYCES CLAVULIGERUS; STRUCTURE ACTIVITY RELATION; X RAY DIFFRACTION;

ANTI-BACTERIAL AGENTS; BACTERIA; CEPHALOSPORINS; HUMANS; PENICILLIN AMIDASE; PROTEIN ENGINEERING;

EID: 33745727403     PISSN: 07388551     EISSN: 15497801     Source Type: Journal    
DOI: 10.1080/07388550600718630     Document Type: Review

References (131)

1. Abbot, B. J., and Fukuda, D. 1975. Physical properties and kinetic properties of a cephalosporin acetyl esterase produced by Bacillus subtilis. Appl. Microbiol. 30: 413-419.
2. Abbot, B. J. 1976. Preparation of pharmaceutical compounds by immobilized enzymes and cells. Adv. Appl. Microbiol. 20, pp. 203-257, D. Perlman, ed., Academic Press, New York.
3. Abraham, E. P., and Newton, G. G. F. 1961. The structure of cephalosporin C. Biochem. J. 79: 377-393.
4. Abraham, E. P., and Loader, P. B. 1972. Cephalosporin C, In: Cephalosporins: Chemistry and Biology. pp. 2-26, E. H. Flynn, ed., Academic Press, New York.
5. Abraham, E. P., and Fawcette P. 1975. Cephalosporin acetylesterase (citrus). Methods in Enzymology, Vol. 43, pp. 728-731. J. Hash, ed., Academic Press, New York.
6. Abraham, E. P., and Newton, G. G. F. 1961. The structure of Cephalosporin C. Biochem. J. 79: 377-393.
7. Alfani, F., Cutarellas, N., Gallifuco, A., Canterella, M., Golini, P., Franzosi, G., and Bianchi, D. 1995. Preliminary investigations for the continuous enzymatic production of 7-aminocephalosporanic acid, In: Enzyme engineering XII, Ann. NY Acad. Sci. Vol. 750, pp. 491-495. Legoy, M. D., Thomas D, eds., New York Academy of Sciences, New York.
8. Alonso-Morales, N. A., Lopez-Gallego, F., Betancor, L., Hidalgo, A., Mateo, C., Fernandez-Lafuente, R., and Guisn, J. M. 2004. Reversible immobilization of glutaryl acylase on SEPABEADS coated with polyethylenimine. Biotechnol. Progr. 20: 533-536.
9. Aramori, I., Fukagawa, M., Tsumura, M., Iwami, M., Yokota, Y., Kojo, H., Kohsaka, M., Udea, Y., and Imenaka, H. 1991a. Isolation of soil strains producing new cephalosporin acylases. J. Ferment. Bioeng. 72: 227-231.
10. Aramori, I., Fukagawa, M., Tsumura, M., Iwami, M., Isogai, T., Ono, H., Ishtani, Y., Kojo, H., Kohsaka, M., Udea, Y., and Imenaka, H. 1991b. Cloning and nucleotide sequencing of new glutaryl-7-ACA and cephalosporin C acylase genes from Pseudomonas strains. J. Ferment. Bioeng. 72: 232-243.
11. Aramori, I., Fukagawa, M., Tsumura, M., Iwami, M., Isogai, T. H., Ishtani, Y., Kojo, H., Kohsaka, M., Udea, Y., and Imenaka, H. 1991c. Cloning and sequencing of a novel glutaryl-7-ACA acylase gene of Bacillus laterosporus and its expression in E. coli and Bacillus subtilis. J. Bacteriol. 173: 7848-7855.
12. Aramori, I., Fukagawa, M., Tsumura, M., Iwami, M., Ono, H., Ishtani, Y., Hiroshi, K., Kojo, H., Kohsaka, M., Udea, Y., and Imenaka, H. 1992. Comparative characterization of new glutaryl-7-ACA acylase. J. Ferment. Bioeng. 73: 185-192.
13. Aramori, I., Fukagawa, M., Tsumura, M., Ono, H., Ishtani, Y., Kojo, H., Kohsaka, M., Udea, Y., and Imenaka, H. 1995. High level production, chemical modification and site directed mutagenesis of a cephalosporin C acylase from Pseudomonas sp. N176. Eur. J. Biochem. 230: 773-778.
14. Aretz, W., and Sauber, K. 1988. Novel D-amino acid transaminase in enzyme engineering (9), Ann. N. Y. Acad. Sci, 542: 366-370, Harvey W. B., and Klibnov, A. M., eds., New York Academy of Sciences, New York.
15. Aretz, W., and Sauber, K. 1990. Gamma-glutamyl-transpeptidase, In: Enzyme Engineering (10), Ann. N. Y. Acad. Sci., 613: 366-370, Okada, H., Tanaka, A., and Blanch, H. W., eds., New York Academy of sciences, New York.
16. Armisen, P., Mateo, C., Cortes, E., Barredo, J. L., Salto, F., Diez, B., Rodes, L., Garcia, J. L., Fernandez-Lafuente, R., and Guisan, J. M. 1998. Selective adsorption of poly-His tagged glutaryl acylase on tailor-made metal chelate supports. J. Chromatog. A. 48: 61-70.
17. Barber, M. S., Giesecke, U., Reichert, A, and Wolfgang, M.2004. Industrial enzymatic production of cephalosporin-based β-lactams. In: Molecular Biotechnology of Fungal β-Lactam Antibiotics and Related Peptide Synthetases, Advances in Biochemical Engineering/Biotechnology, 88: 179-216, Brakhage, A. A., ed. Springer, Berlin.
18. Barends, T. R. M., Yoshida, H., and Dijkstra, B. W. Three-dimensional structures of enzymes useful for β-lactam antibiotic production. Curr. Opin. Biotechnol. 15: 356-383.
19. Battistel, E., Bianchi, D., Bortolo, R., Bonoldi, L. 1998. Purification and stability of glutaryl-7-ACA acylase from Pseudomonas sp. Appl Biochem Biotechnol. 69: 53-67.
20. Beckmann, R., Cantwell, C., Whiteman, P., Queener, S. W., Abraham, E. P. 1993. Production of deacetoxycephalosporin C by transformants of Penicillium chrysogenum: Antibiotic biosynthetic pathway engineering. In: Industrial Microorganisms: Basic and Applied Molecular Genetics, pp. 177-182, Baltz, R. H., Hegeman, G. D., and Skatrud, P.L. (eds). American Society for Microbiology, Washington, DC.
21. Berdy, J. 1989. The discovery of new bioactive metabolites: screening and identification, In: Progress in Ind. Microbiol.27: 3-25, Bushell, M. E., and Grafe, U., eds., Elsevier, Amsterdam.
22. Betina, V. 1994. Structure and activity relationship, In: Bioactive Secondary Metabolites of Microorganisms, Progress in Industrial Microbiology, 30: 236-296. Elsevier, Amsterdam.
23. Bianchi, D., Golini, P., Bortolo, R., Battistel, E., Tassinari, R., and Cesti, P. 1997. Immobilization of glutaryl-7-ACA acylase on aminoalkylated polyacrylic supports. Enzyme Microb. Technol. 20: 368-372.
24. Binder, R. G., Numata, K., Lowe, D. A., Murakami, T., and Brown, J. L. 1993. Isolation and characterization of a Pseudomonas strain producing glutaryl-7-aminocephalosporanic acid acylase. Appl. Environ. Microbiol. 59: 3321-3326.
25. Binder, R. G., Brown, J. L., and Romancik, G. 1994. Biochemical characterization of a glutaryl-7-aminocephalosporanic acid acylase from Pseudomonas strain BLO72. Appl. Environ. Microbiol. 60: 1805-1809.
26. Brannon, D. R., Fukuda, D. S., Mabe, J. A., Huber, F. M., and Whitney, J. G. 1972. Detection of cephalosporin C acetyl esterase in the carbamate cephalosporin antibiotic producing culture, Streptomyces clavuligerus. Antimicrob. Agents Chemother. 1: 237-241.
27. Brotzu, C. G. 1948. Recherché su di nuovo antibiotico, Lav. Ist Igiene Cagliari.
28. Burr, K. W., Ramsden, M., Illing, G. T., Harrison, L. A., Maishman, N. J., Spence, D. W., and Slade, A. 1997. US Pat. Appl. No.: 817900, Assignee: Glaxo Group Limited, (Greenford, GB).
29. Bycroft, B. W., and Shute, R. E. 1987. Chemistry and biosynthesis of penicillins and cephalosporins, In: Penicillium and Acremonium, Biotechnology Handbook; Vol. 1, Peberdy, J. F., ed., pp. 113-160. Plenum Press, New York.
30. Cardoza, R. E., Velasco, J. Martín, J. F., and Liras, P. 2000. A cephalosporin C acetylhydrolase is present in the cultures of Nocardia lactamadurans. Appl. Microbiol. Biotechnol. 54: 406-412.
31. Carrea, G., Corcelli, A., Palmisano, G., and Riva, S. 1996. Preparation of 3-deacetyl cephalosporins by Aspergillus niger lipase. Biotechnol. Bioeng. 52: 648-705.
32. Cole, M., Savidge, T. A., and Vanderhaeghe, H. 1975. Penicillin acylase (assay), In: Methods in Enzymology. 43: 698-705. J. H. Hash, ed., Academic Press, New York.
33. Conlon, H. D., Baqai, J., Baker, K., Shen, Y., Q., Wong, B. L., Noiles, R., and Rausch, C. W. 1995. Two-step immobilized enzyme conversion of cephalosporin C to 7-aminocephalosporanic acid. Biotechnol. Bioeng. 46: 510-513.
34. Coque, J. J. R., Enguita, F. J., Martin, J. F., and Liras, P. 1995. A two protein component 7α-cephem-methoxylase encoded by two genes of the cephamycin C cluster converts cephalosporin C to 7-methoxycephalosporin C. J. Bacteriol. 177: 2230-2235.
35. Crawford, L., Stepan, A. M., McAda, P. C., Rambosek, M. J., Conder, V. A., and Reeves, C. D. 1995. Production of cephalosporin intermediates by feeding adipic acid to recombinant Penicillium chrysogenum strains expressing ring expansion activity. Bio/Technology 13: 58-62.
36. Demain, A. L., Walton, R. B., Newkirk, J. F., and Miller, I. M. 1963. Microbial degradation of cephalosporin C. Nature (London) 199: 909-910.
37. Demain, A. L., and Wolfe, S. 1987. Biosynthesis of cephalosporins, In: Dev. Ind. Microbiol. 27: 175-182.
38. Deshpande, B. S., Ambedkar, S. S., and Shewale, J. G. 1996. Cephalosporin C and penicillin V acylase formation by Aeromonas sp. ACY 95. World J. Microbiol. Biotechnol. 12: 373-378.
39. Durckheimer, W., Adam. F., and Fischer, G. 1988. Recent developments in the field of cephem antibiotics, In: Adv. Drug Res. 17: 161-121, Testa, B., ed., Academic Press, New York.
40. Fechtig, B., Peter, H. H., Bikel, H., and Vischer, E. 1968. Modification of antibiotics, II. Preparation of 7-aminocephalosporanic acid. Helv. Chim. Acta. 51: 1109-1120.
41. Franzosi, G., Battistel, E., Gagliardi, I., and Van der Goes, W. 1995. Screening and characterization of microorganisms with glutaryl-7-ADCA acylase activity. Appl. Microbiol. Biotechnol. 43: 508-513.
42. Frederiksen, R. B., and Emborg, C. 1984. Conversion of cephalosporin C into 7-phenoxy acetoamido-cephalosporanic acid by acyltransferase of mutants of Penicillium chrysogenum. Biotechnol. Lett. 6: 549-554.
43. Golini, P., Bianchi, D., Battistel, E., Cesti, P., and Tassinari, R. 1995. Immobilization of D-amino acid oxidase from different yeasts: Characterization and application in the deamination of cephalosporin C. Enzyme Microb. Technol. 17: 324-329.
44. Hinnen, A., and Nuesch, J. 1976. Enzymatic hydrolysis of cephalosporin C by an extracellular acetyl hydrolase of Cephalosporium acremonium. Antimicrob. Agents Chemother. 9: 824-830.
45. Ho, P. P. K., Towner, R. D., Indelicato, J. M., Wilham, W. J., Spitzer, W. A., and Koppel, G. A. 1973. Biochemical and microbiological studies on 7α-methoxy cephalosporins. J. Antibiot. 26: 313-314.
46. Hodgkin, D. C., and Maslen, E. N. 1961. The X-ray structure of cephalosporin C, Biochem. J. 79: 393-402.
47. 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 beta-subunit of the glutaryl-7-aminocephalosporanic acid acylase of Pseudomonas sp. 130. J. Biol. Chem. 277: 10256-10264.
48. Hwang, T., Fu, H., Lin, L., and Hsu, W. 2000. High level expression of Trigonopsis variabilis D-amino acid oxidase in E. coli using lactose as inducer. Biotechnol. Lett. 22: 655-658.
49. Ichikawa, S., Murai, Y., Yamamato, S., Shibuya, Y., Fuzil., T., Komatsu, K., and Kodaria, R. 1981a. The isolation and properties of Pseudomonas mutant with enhanced productivity of 7-β-(4-carboxybutanamido)cephalosporanic acid acylase. Agric. Biol. Chem. 45: 2225-2229.
50. Ichikawa S., Shibuya, Y., Murai, Y., Yamanato, S., Fuzil, T., Komatsu, K., and Kodaria, R. 1981b. Purification and properties of 7-β-(4- carboxybutanamido)cephalosporanic acid acylase produced by mutant derived from Pseudomonas. Agric. Biol. Chem.45: 2231-2236.
51. Imanaka, H., Miyoshi, T., Konomi, T., Kubochi, Y., Hattori, S., and Kawakita, T. 1983. Process for the preparation of deacetyl cephalosporin U.S. Patent No. 4, 414, 328.
52. Inoue, M., Hiratake, J., Suzuki, H., Kumagai, H., and Sakata, K. 2000. Identification of catalytic nucleophile of Escherichia coli gamma- glutamyltranspeptidase by gamma-monofluorophosphono derivative of glutamic acid: N-terminal thr-391 in small subunit is the nucleophile. Biochemistry 39: 7764-7771.
53. Ishii, Y., Saito, Y., Fujimura, T., Isogai, T., Kojo, H., Yashimata, 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. J. Ferment. Bioeng. 77: 591-597.
54. Ishii, Y., Saito, Y., Fujimura, T., Sasaki, H. T., 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 sp. N176. Eur. J. Biochem. 230: 773-778.
55. Ishiye, M., and Niwa, M. 1992a. Bacterial gamma-glutamyltranspeptidases: comparison of Escherichia coli and Pseudomonas gamma-glutamyltranspeptidase. FEMS Microbiol. Lett. 97: 235-41.
56. Ishiye, M., and Niwa, M. 1992b. Nucleotide sequence and expression in E. coli of the cephalosporin acylase gene of a Pseudomonas strain. Biochim. Biophys. Acta 1132: 233-239.
57. Isogai, T., Fukagawa, M., Aramori, I., Iwami, M., Kojo, H., Ono, T., Udea, Y., Kohsaka, M., and Imanaka, H. 1991. Construction of a 7-Aminocephalosporanic acid (7-ACA) biosynthetic operon and direct production of 7-ACA in Acremonium chrysogenum. Bio/Technology 9: 188-191.
58. Jeffery, J. D., Abraham, A. E. P., and Newton, G. G. F. 1961. Deacetyl-cephalosporin C. Biochem. J. 81: 591-596.
59. Kawate, S., Fukuo, T., Kunito, K., and Kuwahara, Y. 1987. Cephalosporin C acylase, Part II. Purification and characterization of the enzyme. Baiotekunoroji Kenkyu Hokokusho 37: 37-46.
60. Khang, Y. H., and Yoo, B. H. 2000. Isolation and characterization of a novel soil strain, Pseudomonas cepacia BY21, with glutaryl-7- aminocephalosporanic acid acylase activity. Biotech. Lett. 22: 317-320.
61. Kim, Y., Yoon, K., Khang, Y., Turley, S., and Hol, W. G. 2000. The 2.0 A crystal structure of cephalosporin acylase. Structure Fold. Des. 8: 1059-68.
62. Kim, Y., and Hol, W. G. 2001. Structure of cephalosporin acylase in complex with glutaryl-7-aminocephalosporanic acid and glutarate: insight into the basis of its substrate specificity. Chem. Biol. 8: 1253-1264.
63. 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. J. Biol. Chem. 276: 48376-48381.
64. Kim, D.-W., and Yoon, K.-H. 2001. Cloning and high expression of glutaryl-7-aminocephalosporanic acid acylase gene from Pseudomonas diminuta Biotechnol. Letts. 23: 1067-1071
65. Kim, J. K., Yang, I. S., Shin, H. J., Cho, K. J., Ryu, E. K., Kim, S. H., Park, S. S., and Kim, K. H. 2006. Insight into autoproteolytic activation from the structure of cephalosporin acylase: a protein with two proteolytic chemistries. Proc. Natl. Acad. Sci. USA. 103: 1732-1737.
66. Konecny, J., and Sieber, M. 1980. Continuous deacetylation of cephalosporins. Biotechnol. Bioeng. 22: 2013-2029.
67. Kucers, A., Bennett, N. M., and Kemp, R. J. 1991. The Use of Antibiotics (4th ed.), William Heinemann Medical Books, London.
68. Kumar, K. K., Sudhakaran, V. K., Deshpande, B. S., Ambdkar, S. S., and Shewale, J. G. 1993. Cephalosporin acylases: enzyme production structure and applications in the production of 7-ACA. Hind. Antibiot. Bull. 35: 111-125.
69. Kwon, T. H., Rhee, S., Lee, Y. S., Park, S. S., and Kim, K. H. 2000. Crystallization and preliminary X-ray diffraction analysis of glutaryl-7-aminocephalosporanic acid acylase from Pseudomonas sp. GK16. J. Struct. Biol. 131: 79-81.
70. Lee, Y. H., Chang, T. S., Liu, H. J., and Chu, W. S. 1998. An acidic glutaryl-7-aminocephalosporanic acid acylase from Pseudomonas nitroreducens. Biotechnol. Appl. Biochem. 28: 113-118.
71. Lee, Y. S., Kim, H. W., and Park, S. S. 2000. The role of alpha-amino group of the N-terminal serine of beta subunit for enzyme catalysis and autoproteolytic activation of glutaryl 7-aminocephalosporanic acid acylase. J. Biol. Chem. 275: 39200-39206.
72. Lein, J. 1991. One step enzymic conversion of cephalosporin C and derivatives to 7-amino-cephalosporanic acid and derivatives. US Pat. US 4981789.
73. Li, Y., Jiang, W., Yang, Y., Zhao, G., and Wang, E. 1998. Overproduction and purification of glutaryl-7-aminocephalosporanic acid acylase. Protein Expression and Purification 12: 233-238.
74. 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. Eur. J. Biochem. 262: 713-719.
75. Loader, P. B., Newton, G. G. F., and Abraham, E. P. 1961. The cephalosporin C nucleus (7-aminocephalosporanic acid) and some of its derivatives. Biochem. J. 79: 471-476.
76. Lopez-Gallego, F., Betancor, L., Hidalgo, A., Mateo, C., Guisan, J. M., Fernandez-Lafuente, R. 2004. Optimization of an industrial biocatalyst of glutaryl acylase: stabilization of the enzyme by multipoint covalent attachment onto new amino-epoxy Sepabeads. J. Biotechnol. 111: 219-227.
77. Lorenz, W. W., and Wiegel, J. 1997. Isolation, analysis and expression of two genes from Thermoanaerobacterium sp. strain JW/SL YS 485: a β-xylosidase and a novel acetyl xylan esterase with cephalosporin C deacetylase activity. J. Bacteriol. 179: 5436-5441.
78. Mateo, C., Fernandez-Lorente, G., Cortes, E., Garcia, J. L., Fernandez-Lafuente, R., and Guisan, J. M. 2001. One-step purification, covalent immobilization, and additional stabilization of poly-His-tagged proteins using novel heterofunctional chelate-epoxy supports. Biotechnol. Bioeng. 76: 269-276.
79. Matsuda, A., and Komatsu, K. 1985. Molecular cloning and structure of the gene for 7β-(4-carboxybutanamido) cephalosporanic acid acylase from a Pseudomonas strain. J. Bacteriol. 163: 1222-1228.
80. Matsuda, A., Matsumaya, K., Yamamoto, K., Ichikawa, S., and Komatsu, K. 1987a. Cloning and characterization of the genes for two distinct cephalosporin acylases from a Pseudomonas strain. J. Bacteriol. 169: 5815-5820.
81. Matsuda, A., Toma, K., and Komatsu, K. 1987b. Nucleotide sequence of the genes for two distinct cephalosporin C acylases from a Pseudomonas strain. J. Bacteriol. 169: 5821-5826.
82. Matsumoto, K. 1993. Production of 6-APA, 7-ACA and 7-ADCA by immobilized penicillin and cephalosporin amidase, In: Industrial Application of Immobilized Biocatalysis. pp. 67-88. Tanaka, A., Tosa, T., and Koyabayshi, T. eds., Marcel Dekker, New York.
83. Mayr, U., Buckel, P., Brunner, H., Seidel, H., and Stahl, P. (Boehringer Mannheim G.M.B.H.) 1988. Microbial detection system for cephalosporin C acylase. Ger. Offen. DE 3,621,563 (CI. C12Q1/00).
84. Meister, A., Tate, S. S., and Griffith, O. W. 1981. γ-Glutamyl Transpeptidase. Methods in Enzymol. 77: 237-253.
85. Monti, D., Carrea, G., Riva, S., Baldaro, E., and Frare, G. 2000. Characterization of an industrial biocatalyst: Immobilized glutaryl-7-ACA acylase. Biotechnol. Bioeng. 70: 239-244.
86. Morin, R. B., Jackson, B. G., Flynn, E. H., and Roeske, R. W. 1962. Chemistry of cephalosporins antibiotics: 7-Aminocephalosporanic acid from cephalosporin C. J. Am. Chem. Soc. 84: 3400-3401.
87. Morin, R. B., Jackson, B. G., Muller, R. A., Lanvagnino, E. R., Scanlon, W. B., and Andrews, S. L. 1963. Chemistry of cephalosporins: Chemical correlation of penicillin and cephalosporin antibiotics. J. Am. Chem. Soc. 85: 1896-1897.
88. Moss, M. O. 1977. Enzymatic alterations of penicillins and cephalosporins, In: Topics in Enzyme and Fermentation Biotechnology 1, A, pp. 111-131. Wiseman, A., ed., Ellis Norwood, Chichester.
89. Nakayama, R., Kumagai, H., and Tochikura, T. 1984. Purification and properties of γ-glutamyl-transpeptidase from Proteus mirabilis. J. Bacteriol. 160: 341-346.
90. Newton, G. G. F., and Abraham, E. P. 1953. Isolation of penicillanic acid and D-α-aminoadipic acid from cephalosporin N, Nature, 172: 395.
91. Nikolov, A., and Danielsson, B. 1994. Enzymatic transformation of cephalosporin C to 7-aminocephalosporanic acid, I. Cultivation of Pseudomonas syringae and partial purification and immobilization of 7β-(4- carboxybutanamido) cephalosporanic acid acylase. Enzyme and Microb. Technol. 16: 1031-1036.
92. Nobbs, T. J., Ishii, Y., Fujimora, T., Saito Y., and Niwa, M. 1994. Chemical modification and site directed mutagenesis of tyrosine residue in cephalosporin C acylase from Pseudomonas strain N 176. J. Ferment. Bioeng. 77: 604-609.
93. 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. Biochem. Biophys. Res. Commun. 310: 19-27.
94. Onions, A. H. S., and Brady, B. L. 1987 Taxonomy of Penicillium and Acremonium, In: Penicillium and Acremonium, Peberdy, J. F., ed., Biotechnology Handbook, 1. Plenum Press, NY, 1-35.
95. O'Sullivan, J., and Abraham, E. P. 1980 The conversion of cephalosporins to 7α-methoxycephalosporins by cell free extracts of Streptomyces clavuligerus. Biochem. J. 186: 613-616.
96. Otten, L. G., Sio, C. F., Vrielink, J., Cool, R. H., and Quax, W. J. 2002. Altering the substrate specificity of cephalosporin acylase by directed evolution of the β-subunit. J. Biol. Chem. 277: 42121-42127.
97. Palzkill, T., and Botstein, D. 1992. Identification of amino acid substitutes that alter the substrate specificity of TEM-1 beta-lactamase. J. Bacteriol. 172: 5237-5243.
98. Park, S. W., Kim Y. I., Chung, K. H., Hong, S. K., and Kim, S. W. 2002a. Covalent immobilization of GL-7-ACA acylase on silica gel through silanization. Reactive and Functional Polymers 51: 79-92.
99. Park, S. W., Choi, S. Y., Chung, K. H., Hong, S. I., and Kim, S. W. 2002b. Characteristics of GL-7-ACA acylase immobilized on silica gel through silanization. Biochem. Eng. J. 11: 87-93.
100. Park, S. W., Lee, J. W., Hong, S. I., and Kim, S. W. 2003. Immobilization of glutaryl-7-aminocephalosporanic acid acylase on silica gel and enhancement of its stability. Appl. Biochem. Biotechnol. 104: 185-198.
101. Parmar, A., Humar, H., Marwaha, S. S., and Kennedy, J. F. 1998. Recent trends in enzymatic conversion of cephalosporin C to 7-aminocephalosporanic acid (7-ACA). Crit. Rev. Biotechnol. 18: 1-12.
102. Politino, M., Tonzi, S. M., Burnett, W. V., Romancik, G., and Usher, J. J. 1997. Purification and characterization of a cephalosporin esterase from Rhodosporidium toruloides. Appl. Microbiol. Biotechnol. 63: 4807-4811.
103. Richmond, M. H., and Sykes, R. B. 1973. The β-lactamases of gram-negative bacteria and their possible physiological role. Adv. Microbial. Physiol.9: 31-88.
104. Ross, G. W. 1975. β-Lactamases (Enterobacter species). In: Methods Enzymol., 43, pp. 678-687, Hash J.H., ed., Academic Press, New York.
105. Saito, Y., Ishii, Y., Fujimura, T., Sasaki, H. T., Noguchi, Y., Yamada, H., Niwa, M., and Shimomura, K.1996. Protein engineering of a cephalosporin C acylase from strain N176. in Recombinant DNA Biotechnology III: Asenjo, J. A., and Andrews, B. A. ed., Ann. N. Y. Acad. Sci. 782: 226-239.
106. Sakai, Y., Abe, T., Aoki, M., Ohbayashi, Y., Koji, I., Yamamoto, K., Tani, Y., and Kato, N. 1996. Bioconversion of 7-aminocephalosporanic acid by intact Rhodotorula glutinis cells. Appl. Environ. Microbiol. 62: 2669-2672.
107. Sakai, Y., Abe, T., Aoki, M., Ohbayashi, Y., Yamamoto, K., Tani, Y., and Kato, N. 1998a. Purification and properties of cephalosporin esterase from the yeast Rhodotorula glutinis 38B1, useful for bioconversion of 7-aminocephalosporanic acid derivatives. J. Ferment. Bioeng. 85: 53-57.
108. Sakai, Y., Ayukawa, K., Mitsui, R., Yrimoto, H., Yamamoto, K., and Kato, N. 1998b. A novel arylesterase active toward 7-aminocephalosporanic acid from Agrobacterium radiobacter IFO1207: Nucleotide sequence gene expression in Escherichia coli and site directed mutagenesis. J. Ferment. Bioeng. 85: 138-143.
109. Sassiver, M. L., and Lewis, A. 1970. Structure and activity relationship among semisynthetic cephalosporins. Adv. Appl. Microbiol. 13: 163-236.
110. Savidge, T. A. 1984. Enzymatic conversions used in the production of penicillin and cephalosporin. In: Biotechnology of Industrial Antibiotics, pp. 171-224. Vandamme, E. J., ed., Marcel Dekker Co., New York.
111. Schmitt, E. K., Birgit, H., and Ulrich, K. 2004. Regulation of cephalosporin biosynthesis, In: Molecular Biotechnology of Fungal β-Lactam Antibiotics and Related Peptide Synthetases, Series Advances in Biochemical Engineering/Biotechnology, 88, Brakhage, A. A., ed. Springer, Berlin, pp. 1-44.
112. Schrader, T., and Andreesen, J. R. 1996. Properties and chemical modification of D-amino oxidase from Trigonopsis variabilis. Arch. Microbiol. 165: 41-47.
113. Shibuya, Y., Mastsumoto, K., and Fuji, T. 1981. Isolation and properties of 7β-(4-carboxybutanamido) cephalosporanic acid acylase producing bacteria. Agric. Biol. Chem. 45: 1561-1567.
114. Sio, C. F., and Quax, W. J. 2004. Improved β-lactamase and their use as industrial biocatalysts. Curr. Opin. Biotechnol. 15: 349-355.
115. Sjoeberg, B., Nathrost-Westfelt, L., and Ortengren, B. 1967. Enzymatic hydrolysis of some penicillins and cephalosporins by Escherichia coli acylase. Acta Chem. Scand. 21: 547-551.
116. Smith, A. 1985. Cephalosporins In: Comprehensive Biotechnology, 3, M. Moo. Young, ed., Pergamon Press, Oxford, pp. 163-185.
117. Sonawane, V. C., Jolly, R. S., and Vohra, R. M. 1996. Cephalosporin modification: An extracellular glutaryl 7-ACA acylase from Bacillus sp. Biotech. Lett. 18: 965-968.
118. Sudhakaran, V. K., Deshpande, B. S., Ambedkar, S. S., and Shewale, J. G. 1992. Molecular aspects of penicillins and cephalosporin acylases. Process. Biochem. 27: 131-143.
119. Suzuki, H., Miwa, C., Ishihara, S., and Kumagai, H. 2004. A single amino acid substitution Converts γ-glutamyltranspeptidase to a Class IV cephalosporin acylase (glutaryl-7-aminocephalosporanic acid acylase). Appl. Environ. Microbiol. 70: 6324-6328.
120. Sykes, R. B., and Matthew, M. 1976. The β-lactamases of gram negative bacteria and their role in resistance to β-lactam antibiotics. J. Antimicrob. Chemother. 2: 115-157.
121. Szwajcer, E., and Mosbach, K. 1985 Isolation and partial characterization of a D-amino acid oxidase active against cephalosporin C from yeast Trigonopsis variabilis. Biotechnol. Letts. 7: 1-7.
122. Takimoto, A., Matsushima, K., Yagi, S., and Sonoyama, T. 1994. Purification and characterization and partial amino acid sequence of a novel cephalosporin C deacetylase from Bacillus subtilis. J. Ferment. Bioeng. 77: 17-22.
123. Tischer, W., Giesecke, U., Lang, G., and Roder, A., and Wedekind, F. 1992. Biocatalytic 7-ACA production, Ann. N. Y. Acad. Sci. 672: 502-509.
124. Velasco, J., Luis, A.J., Angel, M. M., Diez, B., Soler, G., and Barredo, J. L. 2000. Environmentally safe production of 7-aminodeacetoxycephalosporanic acid (7-ADCA) using recombinant strains of Acremonium chrysogenum. Nat. Biotechnol. 18: 857-861.
125. Vicenzi, J. T., and Hansen, G. J. 1993. Enzymatic oxidation of cephalosporin C using whole cells of the yeast Trigonopsis variabilis within a "cross-flow filter reactor." Enzyme. Microbial. Technol. 15: 281-285.
126. Wildfeuer, M. E. 1994. Aqueous acetylation of deacetyl glutaryl-7-aminocephalosporanic acid and speculation on the origin of deacetyl cephalosporin C in fermentation broth. J. Antibio. 47: 64-71.
127. Yau, M. H., Wang, J., Tsang, P. W., and Fong, W. P. 2006. J1 acylase, a glutaryl-7-aminocephalosporanic acid acylase from Bacillus laterosporus J1, is a member of the alpha/beta-hydrolase fold superfamily. FEBS Lett. 580: 1465-1471.
128. Zhang, Q. J., and Xu, W. X. 1993. Morphological physiological and enzymatic characteristics of cephalosporin acylase producing Arthrobacter strain 45-A. Arch. Microbiol. 159: 392-395.
129. Zhang, Q., Xu, W., and Shi, L. 1991. 2-Nitro-5-(6-bromohexanoylamino) benzoic acid test paper method for detecting microorganisms capable of producing cephalosporin acylases. Anal. Biochem. 196: 201-206.
130. Zhang, W., Liu Y., Zheng, H., Yang, S., and Jiang, W. 2005. Improving the activity and stability of GL-7-ACA acylase CA130 by site-directed mutagenesis. Appl. Environ. Microbiol. 71: 5290-5296.
131. Zhu, S., Yang, S., Zhao, G., and Jiang, W. 2003. A rapid and specific method to screen environmental microorganisms for cephalosporin acylase activity. J. Microbiol. Methods 54: 131-135.