The mechanism of catalysis and the inhibition of the Bacillus cereus zinc-dependent β-lactamase

Biochemical Journal

Volumn 331, Issue 3, 1998, Pages 703-711

  Bounaga, Sakina ^a   Laws, Andrew P ^a   Galleni, Moreno ^b   Page, Michael I ^a  

^a UNIVERSITY OF HUDDERSFIELD   (United Kingdom)

^b CHU SART TILMAN   (Belgium)

Author keywords

[No Author keywords available]

Indexed keywords

ACETANILIDE; ASPARTIC ACID; BETA LACTAMASE; CARBOXYLIC ACID DERIVATIVE; CEPHALOSPORIN; PENICILLIN G; PROTON; THIOL;

ARTICLE; BACILLUS CEREUS; COVALENT BOND; DRUG HYDROLYSIS; ENZYME INHIBITION; ENZYME MECHANISM; MICHAELIS CONSTANT; NONHUMAN; PH; PKA; PRIORITY JOURNAL;

BACILLUS CEREUS; BACTERIA (MICROORGANISMS); FELIS CATUS; POSIBACTERIA;

EID: 0032080039     PISSN: 02646021     EISSN: None     Source Type: Journal    
DOI: 10.1042/bj3310703     Document Type: Article

References (73)

1. Sykes, R. B. and Matthe, M. (1976) J. Antimicrob. Chemother. 2, 115-157
2. Medeiros, A. A. (1984) Br. Med. Bull. 40, 18-27
3. Waley, S. G. (1992) in The Chemistry of β-Lactams (Page, M. I., ed.), pp. 198-228, Chapman and Hall, London
4. Jaurin, B. and Gundström, T. (1981) Proc. Natl. Acad. Sci. U.S.A. 78, 4897-4901
5. Dale, J. W., Godwin, D., Mossakowska, D., Stephenson, P. and Wall, S. (1985) FEBS Lett. 191, 39-44
6. Ambler, R. P., Coulson, A. F. W., Frère, J.-M., Ghuysen, J.-M., Joris, B., Forsman, M., Levesque, R. C., Tiraby, G. and Waley, S. G. (1991) Biochem. J. 276, 269-272
7. Joris, B., Ledent, P., Dideberg, O., Fonzè, E., Lamotte-Brassuer, J., Kelly, A., Ghuysen, J. and Frère, J.-M. (1991) Antimicrob. Agents Chemother. 35, 2294-2301
8. Kubawara, S. and Abraham, E. P. (1967) Biochem. J. 103, 23C-30C
9. Saino, Y., Kobayashi, F., Inoue, M. and Mitsuhashi, S. (1982) Antimicrob. Agents Chemother. 34, 1590-1592
10. Bicknell, R., Emanuel, E. L., Gagnon, J. and Waley, S. G. (1985) Biochem. J. 229, 791-797
11. Iaconis, J. P. and Sanders, C. C. (1990) Antimicrob. Agents Chemother. 34, 44-51
12. Cuchural, Jr., G. J., Malamy, M. H. and Tally, F. P. (1986) Antimicrob. Agents Chemother. 30, 645-648
13. Bandoh, K., Myto, Y., Watanabe, K., Katoh, N. and Ueno, K. (1991) Antimicrob. Agents Chemother. 35, 371-372
14. Payne, D. J. (1993) J. Med. Microbiol. 39, 93-99
15. Felici, A., Amicosante, G., Oratore, A., Strom, R., Ledent, P., Joris, B., Fanuel, L. and Frère, J.-M. (1993) Biochem. J. 291, 151-155
16. Lim, H. M., Pène, J. J. and Shaw, R. (1988) J. Bacteriol. 170, 2873-2878
17. Frère, J.-M. (1995) Mol. Microbiol. 16, 385-395
18. Massidda, O., Rossolini, G. M. and Salta, G. (1991) J. Bacteriol. 173, 4611-1617
19. Rasmussen, B. A., Gluzman, Y. and Tally, F. P. (1990) Antimicrob. Agents Chemother. 34, 1590-1592
20. Thompson, J. S. and Malamy, M. H. (1990) J. Bacteriol. 172, 2584-2593
21. Hussain, M., Carlino, A., Madonnam, M. J. and Lampen, J. O. (1985) J. Bacteriol. 164, 223-229
22. Ambler, R. P., Daniel, M., Fleming, J., Hermoso, J.-M., Pang, C. and Waley, S. G. (1986) FEBS Lett. 189, 207-211
23. Sutton, B. J., Artymiuk, P. J., Cordero-Borboa, A. E., Little, C., Phillips, D. C. and Waley, S. G. (1987) Biochem. J. 248, 181-188
24. Carfi, A., Pares, S., Duée, E., Galleni, M., Duez, C., Frère, J.-M. and Dideberg, O. (1995) EMBO J. 14, 4914-4921
25. Davies, R. B. and Abraham, E. P. (1974) Biochem. J. 143, 129-135
26. Baldwin, G. S., Galdes, A., Hill, H. A. O., Smith, B. E., Waley, S. G. and Abraham, E. P. (1978) Biochem. J. 175, 441-447
27. Concha, N. O., Rasmussen, B. A., Nush, K. and Herzberg, O. (1966) Structure 4, 823-637
28. Carfi, A., Paul-Soto, R., Martin, L., Petillot, Y., Frère, J.-M. and Dideberg, O. (1997) Acta Crystallogr. Sect. D: Biol. Crystallogr. D53, 485-487
29. Crowder, M. W., Wang, Z., Franklin, S. C., Zovinka, E. P. and Benkovic, S. J. (1996) Biochemistry 35, 12126-12132
30. Little, C., Emanuel, E. L., Gagnon, J. and Waley, S. G. (1986) Biochem. J. 233, 465-469
31. Lim, H. M. and Pène, J. J. (1989) J. Biol. Chem. 264, 11682-11687
32. Lim, H. M., Iyer, R. K. and Pène, J. J. (1991) Biochem. J. 276, 401-404
33. Laws, A. P., Layland, N. J., Proctor, D. G. and Page, M. I. (1993) J. Chem. Soc. Perkin Trans. 2, 17-21
34. Bicknell, R., Knott-Junziker, V. and Waley, S. G. (1983) Biochem. J. 213, 61-66
35. Cleland, W. W. (1977) Adv. Enzymol. Rel. Areas Mol. Biol. 45, 273-387
36. Fersht, A. R. (1985) Enzyme Structure and Mechanism, W. H. Freeman, New York
37. Perrin, D. D. (1982) Ionisation Constants of Inorganic Acids and Bases in Aqueous Solution, 2nd edn., Pergamon, Oxford
38. Pocker, Y. and Bjorkquist, D. W. (1977) Biochemistry 16, 5698-5707
39. Kimura, E., Shiota, T., Koike, T., Shiro, M. and Kodama, M. (1990) J. Am. Chem. Soc. 112, 5805-5811
40. Mock, W. L. and Tsay, J.-T. (1986) Biochemistry 25, 2920-2927
41. Mock, W. L. and Tsay, J.-T. (1988) J. Biol. Chem. 263, 8635-8641
42. Kaiser, E. T. and Kaiser, B. L. (1972) Acc. Chem. Res. 5, 219-224
43. Suh, J. and Kaiser, E. T. (1976) J. Am. Chem. Soc. 98, 1940-1947
44. Christianson, D. W., David, P. R. and Lipscomb, W. N. (1987) Proc. Natl. Acad. Sci. U.S.A. 84, 1512-1515
45. Osumi, A., Rahmo, A., King, S. W., Przystas, T. L. and Fife, T. H. (1994) Biochemistry 33, 14750-14757
46. Rees, D. C., Lewis, M. and Lipscomb, W. N. (1983) J. Mol. Biol. 168, 367-387
47. Bertini, I., Luchinat, C., Rosi, M., Sgamelloti, A. and Tarantelli, F. (1990) Inorg. Chem. 29, 1460-1463
48. Christiansen, D. W. and Fierke, C. A. (1996) Acc. Chem. Res. 29, 331-339
49. Xiang, S. B., Short, S. A., Wolfenden, R. and Carter, C. W. (1996) Biochemistry 35, 1335-1341
50. Kiefer, L. L. and Fierke, C. A. (1994) Biochemistry 33, 15233-15240
51. Davis, A. M., Proctor, P. and Page, M. I. (1991) J. Chem. Soc. Perkin Trans. 2, 1213-1217
52. Christianson, D. W. and Lipscomb, W. N. (1989) Acc. Chem. Res. 22, 62-69
53. Breslow, R., Chin, J., Hilvert, D. and Trainor, G. (1983) Proc. Natl. Acad. Sci. U.S.A. 80, 4585-4589
54. Breslow, R. and Schepartz, A. (1987) Chem. Lett. 1-4
55. Lee, S., Hwang, B. K., Myoung, Y. C. and Suh, J. (1995) Bioorganic Chem. 23, 183-192
56. Banci, L., Bertini, I. and La Penna, H. (1994) Proteins: Struct. Funct. Genet. 18, 186-197
57. Mustafi, D. and Markinen, M. W. (1994) J. Biol. Chem. 269, 4587-4595
58. Britt, B. M. and Peticolas, W. L. (1992) J. Am. Chem. Soc. 114, 5295-5303
59. Suh, J., Cho, W. and Chung, S. (1985) J. Am. Chem. Soc. 107, 4530-4535
60. Page, M. I. (1992) in The Chemistry of β-Lactam Antibiotics (Page, M. I., ed.), pp. 79-100, and 128-147, Blackie, Glasgow
61. Page, M. I. (1987) Adv. Phys. Org. Chem. 23, 165-270
62. Page, M. I. (1984) Acc. Chem. Res. 17, 144-151
63. Proctor, P., Gensmantel, N. P. and Page, M. I. (1982) J. Chem. Soc. Perkin Trans. 2, 1185-1192
64. Gensmantel, N. P., Proctor, P. and Page, M. I. (1980) J. Chem. Soc. Perkin Trans. 2, 1725-1732
65. DeWolfe, R. H. and Newcomb, R. C. (1971) J. Org. Chem. 36, 3870-3878
66. Eriksson, S. O. (1968) Acta Chem. Scand. 22, 892-906
67. Young, J. K., Pazhanisamay, S. and Schowen, R. L. (1984) J. Org. Chem. 49, 4148-4152
68. Menger, F. M. and Donohue, J. A. (1973) J. Am. Chem. Soc. 95, 432-437
69. Brown, R. S., Bennet, A. J. and Slebocka-Tilk, H. (1992) Acc. Chem. Res. 25, 481-488
70. Page, M. I. and Williams, A. (1997) Organic and Bioorganic Mechanisms, pp. 80-96, Longman, Harlow
71. Gensmantel, N. P., Gowling, E. W. and Page, M. I. (1978) J. Chem. Soc. Perkin Trans. 2, 335-342
72. Kresge, A. J. and Lin, A. C. (1975) J. Am. Chem. Soc. 97, 6257-6258
73. Pocker, Y. (1959) Chem. Inc. (London) 1383-1384