Sulbactam forms only minimal amounts of irreversible acrylate-enzyme with SHV-1 β-lactamase

Biochemistry

Volumn 46, Issue 31, 2007, Pages 8980-8987

  Totir, Monica A ^a,b   Helfand, Marion S ^a,c   Carey, Marianne P ^a   Sheri, Anjaneyulu ^d   Buynak, John D ^d   Bonomo, Robert A ^a,c   Carey, Paul R ^a,b  

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

^b CASE WESTERN RESERVE UNIVERSITY   (United States)

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

^d SOUTHERN METHODIST UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

DEGRADATION; ISOMERIZATION; SINGLE CRYSTALS; X RAY CRYSTALLOGRAPHY;

RAMAN MICROSCOPY; SUBSEQUENT ISOMERIZATION;

ENZYME INHIBITION;

ACRYLIC ACID; AMINO ACID; BETA LACTAM DERIVATIVE; BETA LACTAMASE; DEUTERIUM; ENAMINE; IMINE; SERINE; SULBACTAM;

ARTICLE; CHEMICAL REACTION; CIS TRANS ISOMERISM; CROSS LINKING; DEGRADATION; ENZYME ACTIVE SITE; ENZYME INHIBITION; HYDROGEN BOND; ISOMERIZATION; MICROSCOPY; PRIORITY JOURNAL; QUANTUM MECHANICS; RAMAN MICROSCOPY; RAMAN SPECTROMETRY; X RAY CRYSTALLOGRAPHY;

ACRYLATES; AMINO ACID SUBSTITUTION; BETA-LACTAMASES; CATALYTIC DOMAIN; CLAVULANIC ACID; CRYSTALLIZATION; ENZYME INHIBITORS; IMINES; KINETICS; MOLECULAR STRUCTURE; PENICILLANIC ACID; RECOMBINANT PROTEINS; SERINE; SPECTRUM ANALYSIS, RAMAN; SULBACTAM;

EID: 34547820173     PISSN: 00062960     EISSN: None     Source Type: Journal    
DOI: 10.1021/bi7006146     Document Type: Article

References (20)

1. Helfand, M., and Bonomo, R. (2003) β-Lactamases: A Survey of Protein Diversity, Curr. Drug Targets 3, 9-23.
2. Brenner, D. G., and Knowles, J. R. (1981) Penicillanic Acid Sulfone: An Unexpected Isotope Effect in the Interaction of 6a-and 6b-Monodeuterio and of 6,6-Dideuterio Derivatives with RTEM β-Lactamase from Escherichia coli, Biochemistry 20, 3680-3687.
3. Bonomo, R. A., Dawes, C. G., Knox, J. R., and Shlaes, D. M. (1995) β-Lactamase mutations far from the active site influence inhibitor binding, Biochim. Biophys. Acta 1247, 121-125.
4. Bush, K., Clarissa, M., Rasmussen, B. A., Lee, V. J., and Yang, Y. (1993) Kinetic Interactions of Tazobactam with β-Lactamases from All Major Structural Classes, Antimicrob. Agents Chemother. 37, 851-858.
5. Brown, R. P. A., Aplin, R. T., and Schofield, C. J. (1996) Inhibition of TEM-2 β-Lactamase from Escherichia coli by Clavulanic Acid: Observation of Intermediates by Electrospray Ionization Mass Spectrometry, Biochemistry 35, 12421-12432.
6. Yang, Y., Janota, K., Tabei, K., Huang, N., Siegel, M. M., Lin, Y.-I., Rasmussen, B. A., and Shlaes, D. M. (2000) Mechanism of Inhibition of the Class A b-Lactamases PCI and TEM-1 by Tazobactam: Observation of Reaction Products by Electrospray Ionization Mass Spectrometry, J. Biol. Chem. 275, 26674-26682.
7. Chen, C. C. H., and Herzberg, O. (1992) Inhibition of β-lactamase by clavulanate: Trapped intermediates in cryocrystallographic studies, J. Mol. Biol. 224, 1103-1113.
8. Kuzin, A. P., Nukaga, M., Nukaga, Y., Hujer, A., Bonomo, R. A., and Knox, J. R. (2001) Inhibition of the SHV-1 beta-Lactamase by Sulfones: Crystallographic Observation of Two Reaction Intermediates with Tazobactam, Biochemistry 40, 1861-1866.
9. Helfand, M. S., Totir, M. A., Carey, M. P., Hujer, A. M., Bonomo, R. A., and Carey, P. R. (2003) Following the Reactions of Mechanism-Based Inhibitors with β-Lactamase by Raman Crystallography, Biochemistry 42, 13386-13392.
10. Padayatti, P. S., Helfand, M. S., Totir, M. A., Carey, M. P., Carey, P. R., Bonomo, R. A., and van den Akker, F. (2005) High Resolution Crystal Structures of the trans-Enamine Intermediates Formed by Sulbactam and Clavulanic Acid and E166A SHV-1 {beta}-Lactamase, J. Biol. Chem. 280, 34900-34907.
11. Padayatti, P. S., Helfand, M. S., Totir, M. A., Carey, M. P., Hujer, A. M., Carey, P. R., Bonomo, R. A., and Akker, F. v. d. (2004) Tazobactam Forms a Stoichiometric trans-Enamine Intermediate in the E166A Variant of SHV-1 β-Lactamase: 1.63 Å Crystal Structure, Biochemistry 43, 843-848.
12. Totir, M. A., Padayatti, P. S., Helfand, M. S., Carey, M. P., Bonomo, R. A., Carey, P. R., and Akker, F. v. d. (2006) Effect of the Inhibitor-Resistant M69V Substitution on the Structures and Populations of trans-Enamine beta-Lactamase Intermediates, Biochemistry 45, 11895-11904.
13. Helfand, M. S., Hujer, A. M., Sonnichsen, F. D., and Bonomo, R. A. (2002) Unexpected Advanced Generation Cephalosporinase Activity of the Met69Phe Variant of SHV β-Lactamase, J. Biol. Chem. 277, 47719-47723.
14. Hujer, A. M., Hujer, K. M., and Bonomo, R. A. (2001) Mutagenesis of amino acid residues in the SHV-1 β-lactamase: the premier role of Gly238Ser in penicillin and cephalosporin resistance, Biochim. Biophys. Acta 1547, 37-50.
15. Kuzin, A. P., Nukaga, M., Nukaga, Y., Hujer, A. M., Bonomo, R. A., and Knox, J. R. (1999) Structure of the SHV-1 beta-lactamase, Biochemistry 38, 5720-5727.
16. Altose, M. D., Zheng, Y., Dong, J., Palfey, B. A., and Carey, P. R. (2001) Comparing protein-ligand interactions in solution and single crystals by Raman spectroscopy, Proc. Natl. Acad. Sci. U.S.A. 98, 3006-3011.
17. Dong, J., Swift, K., Matayoshi, E., Nienaber, V. L., Weitzberg, M., Rockway, T., and Carey, P. R. (2001) Probing Inhibitors Binding to Human Urokinase Crystals by Raman Microscopy: Implications for Compound Screening, Biochemistry 40, 9751-9757.
18. Frisch, M. J., Trucks, G. W., Schlegel, H. B., Scuseria, G. E., Robb, M. A., Cheeseman, J. R., Montgomery, J. A., Jr., Vreven, T., Kudin, K. N., Burant, J. C., Millam, J. M., Iyengar, S. S., Tomasi, J., Barone, V., Mennucci, B., Cossi, M., Scalmani, G., Rega, N., Petersson, G. A., Nakatsuji, H., Hada, M., Ehara, M., Toyota, K., Fukuda, R., Hasegawa, J., Ishida, M., Nakajima, T., Honda, Y., Kitao, O., Nakai, H., Klene, M., Li, X., Knox, J. E., Hratchian, H. P., Cross, J. B., Bakken, V., Adamo, C., Jaramillo, J., Gomperts, R., Stratmann, R. E., Yazyev, O., Austin, A. J., Cammi, R., Pomelli, C., Ochterski, J. W., Ayala, P. Y., Morokuma, K., Voth, G. A., Salvador, P., Dannenberg, J. J., Zakrzewski, V. G., Dapprich, S., Daniels, A. D., Strain, M. C., Farkas, O., Malick, D. K., Rabuck, A. D., Raghavachari, K., Foresman, J. B., Ortiz, J. V., Cui, Q., Baboul, A. G., Clifford, S., Cioslowski, J., Stefanov, B. B., Liu, G., Liashenko, A., Piskorz, P., Komaromi, I., Martin, R. L., Fox, D. J., Keith, T., Al-Laham, M. A., Peng, C. Y., Nanayakkara, A., Challacombe, M., Gill, P. M. W., Johnson, B., Chen, W., Wong, M. W., Gonzalez, C., and Pople, J. A. (2004) Gaussian 03, revision C.02, Gaussian, Inc., Wallingford, CT.
19. Nagel, Z. D., and Klinman, J. P. (2006) Tunneling and Dynamics in Enzymatic Hydride Transfer, Chem. Rev. 106, 3095-3118.
20. Carey, P. R. (2006) Spectroscopic Characterization of Distortion in Enzyme Complexes, Chem. Rev. 106, 3043-3054.