Crystal structure of a preacylation complex of the β-lactamase inhibitor sulbactam bound to a sulfenamide bond-containing thiol-β- lactamase

Journal of the American Chemical Society

Volumn 134, Issue 40, 2012, Pages 16798-16804

  Rodkey, Elizabeth A ^a   Drawz, Sarah M ^b   Sampson, Jared M ^a,c   Bethel, Christopher R ^b   Bonomo, Robert A ^a,b   Van Den Akker, Focco ^a  

^a CASE WESTERN RESERVE UNIVERSITY SCHOOL OF MEDICINE   (United States)

^b LOUIS STOKES CLEVELAND VA MEDICAL CENTER   (United States)

^c NEW YORK UNIVERSITY SCHOOL OF MEDICINE   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ACTIVE SITE; CARBONYL MOIETY; CATALYTIC RESIDUE; CLASS A; GAIN INSIGHT; INHIBITOR COMPLEX; INHIBITOR DESIGN; KLEBSIELLA PNEUMONIAE; LACTAMASES; OXYANION HOLE; PENICILLIN-BINDING PROTEINS; STRUCTURE-BASED; SULFENAMIDES; WILD TYPES;

BACTERIA;

AMINO ACIDS;

BETA LACTAMASE INHIBITOR; CEFALOTIN; CEFAMANDOLE; CLAVULANIC ACID; SULBACTAM; SULFENAMIDE DERIVATIVE; TAZOBACTAM;

ACYLATION; ARTICLE; CATALYSIS; CRYSTAL STRUCTURE; ENZYME ACTIVITY; GENE MUTATION; KLEBSIELLA PNEUMONIAE; NONHUMAN;

ANTI-BACTERIAL AGENTS; BETA-LACTAMASES; CATALYTIC DOMAIN; CRYSTALLOGRAPHY, X-RAY; KLEBSIELLA PNEUMONIAE; MODELS, MOLECULAR; POINT MUTATION; SULBACTAM;

EID: 84867339853     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja3073676     Document Type: Article

References (46)

1. Essack, S. Y. Pharm. Res. 2001, 18, 1391-1399
2. Miller, L. A.; Ratnam, K.; Payne, D. J. Curr. Opin. Pharmacol. 2001, 1, 451-458
3. Bush, K.; Macielag, M. J. Expert Opin. Ther. Pat. 2010, 20, 1277-1293
4. Totir, M. A.; Padayatti, P. S.; Helfand, M. S.; Carey, M. P.; Bonomo, R. A.; Carey, P. R.; van den Akker, F. Biochemistry 2006, 45, 11895-11904
5. Drawz, S. M.; Bonomo, R. A. Clin. Microbiol. Rev. 2010, 23, 160-201
6. Helfand, M. S.; Bethel, C. R.; Hujer, A. M.; Hujer, K. M.; Anderson, V. E.; Bonomo, R. A. J. Biol. Chem. 2003, 278, 52724-52729
7. Padayatti, P. S.; Helfand, M. S.; Totir, M. A.; Carey, M. P.; Carey, P. R.; Bonomo, R. A.; van den Akker, F. J. Biol. Chem. 2005, 280, 34900-34907
8. Padayatti, P. S.; Helfand, M. S.; Totir, M. A.; Carey, M. P.; Hujer, A. M.; Carey, P. R.; Bonomo, R. A.; van den Akker, F. Biochemistry 2004, 43, 843-848
9. Padayatti, P. S.; Sheri, A.; Totir, M. A.; Helfand, M. S.; Carey, M. P.; Anderson, V. E.; Carey, P. R.; Bethel, C. R.; Bonomo, R. A.; Buynak, J. D.; van den Akker, F. J. Am. Chem. Soc. 2006, 128, 13235-13242
10. Chen, C. C.; Herzberg, O. J. Mol. Biol. 1992, 224, 1103-1113
11. Kuzin, A. P.; Nukaga, M.; Nukaga, Y.; Hujer, A.; Bonomo, R. A.; Knox, J. R. Biochemistry 2001, 40, 1861-1866
12. Chen, Y.; Shoichet, B.; Bonnet, R. J. Am. Chem. Soc. 2005, 127, 5423-5434
13. Wang, X.; Minasov, G.; Blazquez, J.; Caselli, E.; Prati, F.; Shoichet, B. K. Biochemistry 2003, 42, 8434-8444
14. Ke, W.; Sampson, J. M.; Ori, C.; Prati, F.; Drawz, S. M.; Bethel, C. R.; Bonomo, R. A.; van den Akker, F. Antimicrob. Agents Chemother. 2011, 55, 174-183
15. Caselli, E.; Powers, R. A.; Blasczcak, L. C.; Wu, C. Y.; Prati, F.; Shoichet, B. K. Chem. Biol. 2001, 8, 17-31
16. Beadle, B. M.; Trehan, I.; Focia, P. J.; Shoichet, B. K. Structure 2002, 10, 413-424
17. Tremblay, L. W.; Xu, H.; Blanchard, J. S. Biochemistry 2010, 49, 9685-9687
18. Sigal, I. S.; Harwood, B. G.; Arentzen, R. Proc. Natl. Acad. Sci. U.S.A. 1982, 79, 7157-7160
19. Sigal, I. S.; DeGrado, W. F.; Thomas, B. J.; Petteway, S. R. J. Biol. Chem. 1984, 259, 5327-5332
20. Rice, L. B.; Carias, L. L.; Hujer, A. M.; Bonafede, M.; Hutton, R.; Hoyen, C.; Bonomo, R. A. Antimicrob. Agents Chemother. 2000, 44, 362-367
21. Otwinowski, Z.; Minor, W. (1997, 276, 307-326.
22. Winn, M. D. Acta Crystallogr., Sect. D: Biol. Crystallogr. 2011, 67, 235-242
23. Emsley, P.; Cowtan, K. Acta Crystallogr., Sect. D: Biol. Crystallogr. 2004, 60, 2126-2132
24. Schuttelkopf, A. W.; van Aalten, D. M. Acta Crystallogr., Sect. D: Biol. Crystallogr. 2004, 60, 1355-1363
25. Imtiaz, U.; Billings, E. M.; Knox, J. R.; Mobashery, S. Biochemistry 1994, 33, 5728-5738
26. Vanhove, M.; Guillaume, G.; Ledent, P.; Richards, J. H.; Pain, R. H.; Frere, J. M. Biochem. J. 1997, 321 (Pt 2) 413-417
27. Hermann, J. C.; Pradon, J.; Harvey, J. N.; Mulholland, A. J. J. Phys. Chem. A 2009, 113, 11984-11994
28. Zafaralla, G.; Manavathu, E. K.; Lerner, S. A.; Mobashery, S. Biochemistry 1992, 31, 3847-3852
29. Majiduddin, F. K.; Materon, I. C.; Palzkill, T. G. Int. J. Med. Microbiol. 2002, 292, 127-137
30. Thomas, V. L.; Golemi-Kotra, D.; Kim, C.; Vakulenko, S. B.; Mobashery, S.; Shoichet, B. K. Biochemistry 2005, 44, 9330-9338
31. Prinarakis, E. E.; Miriagou, V.; Tzelepi, E.; Gazouli, M.; Tzouvelekis, L. S. Antimicrob. Agents Chemother. 1997, 41, 838-840
32. Dubois, V.; Poirel, L.; Demarthe, F.; Arpin, C.; Coulange, L.; Minarini, L. A.; Bezian, M. C.; Nordmann, P.; Quentin, C. Antimicrob. Agents Chemother. 2008, 52, 3792-3794
33. Bret, L.; Chaibi, E. B.; Chanal-Claris, C.; Sirot, D.; Labia, R.; Sirot, J. Antimicrob. Agents Chemother. 1997, 41, 2547-2549
34. Lobkovsky, E.; Moews, P. C.; Liu, H.; Zhao, H.; Frere, J. M.; Knox, J. R. Proc. Natl. Acad. Sci. U.S.A. 1993, 90, 11257-11261
35. Thomson, J. M.; Distler, A. M.; Prati, F.; Bonomo, R. A. J. Biol. Chem. 2006, 281, 26734-26744
36. Salmeen, A.; Andersen, J. N.; Myers, M. P.; Meng, T. C.; Hinks, J. A.; Tonks, N. K.; Barford, D. Nature 2003, 423, 769-773
37. van Montfort, R. L.; Congreve, M.; Tisi, D.; Carr, R.; Jhoti, H. Nature 2003, 423, 773-777
38. Massova, I.; Kollman, P. A. J. Comput. Chem. 2002, 23, 1559-1576
39. Lamotte-Brasseur, J.; Lounnas, V.; Raquet, X.; Wade, R. C. Protein Sci. 2008, 8, 404-409
40. Knap, A. K.; Pratt, R. F. Biochem. J. 1991, 273 (Pt 1) 85-91
41. Minasov, G.; Wang, X.; Shoichet, B. K. J. Am. Chem. Soc. 2002, 124, 5333-5340
42. Strynadka, N. C.; Adachi, H.; Jensen, S. E.; Johns, K.; Sielecki, A.; Betzel, C.; Sutoh, K.; James, M. N. Nature 1992, 359, 700-705
43. Golemi-Kotra, D.; Meroueh, S. O.; Kim, C.; Vakulenko, S. B.; Bulychev, A.; Stemmler, A. J.; Stemmler, T. L.; Mobashery, S. J. Biol. Chem. 2004, 279, 34665-34673
44. Meroueh, S. O.; Fisher, J. F.; Schlegel, H. B.; Mobashery, S. J. Am. Chem. Soc. 2005, 127, 15397-15407
45. Krissinel, E.; Henrick, K. Acta Crystallogr., Sect. D: Biol. Crystallogr. 2004, 60, 2256-2268
46. Kabsch, W. Acta Crystallogr., Sect. A 1976, 32, 922-923