Crystal structure of 6α-(hydroxymethyl)penicillanate complexed to the TEM-1 β-lactamase from Escherichia coli: Evidence on the mechanism of action of a novel inhibitor designed by a computer-aided process

Journal of the American Chemical Society

Volumn 118, Issue 32, 1996, Pages 7435-7440

  Maveyraud, Laurent ^a   Massova, Irina ^b   Birck, Catherine ^a   Miyashita, Kazuyuki ^b   Samama, Jean Pierre ^a   Mobashery, Shahriar ^b  

^a INSTITUT DE PHARMACOLOGIE ET DE BIOLOGIE STRUCTURALE   (France)

^b WAYNE STATE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

6ALPHA (HYDROXYMETHYL)PENICILLANIC ACID; BETA LACTAMASE; PENICILLANIC ACID DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; COMPLEX FORMATION; COMPUTER SIMULATION; CRYSTALLOGRAPHY; DRUG DESIGN; ENZYME BINDING; ESCHERICHIA COLI;

EID: 0029738864     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja9609718     Document Type: Article

References (20)

1. Miyashita, K.; Massova, I.: Taibi, P.; Mobashery, S. J. Am. Chem. Soc. 1995, 117, 11055.
2. Bulychev, A.; Massova, I.; Lerner, S. A.; Mobashery, S. J. Am. Chem. Soc. 1995, 1/7, 4797.
3. Bulychev, A.; O'Brien, M. E.; Massova, I.; Teng, M.; Gibson, T. A.; Miller, M. J.; Mobashery, S. J. Am. Chem. Soc. 1995, 117, 5938.
4. Jelsch, C.; Lenfant, F.; Masson, J. M.; Samama, S. P. J. Mol. Biol. 1992, 223, 377.
5. Leslie, A. G. W. In Computational aspects of protein crystal data anahsis, Proceedings of the CCP4 Study Weekend''compiled by Helliwell. J. R., Machin, P. A., Papiz, M. Z.; Daresbury Laboratory, pp 39-50.
6. Collaborative Computational Project Number 4. Acta Crystallogr. 1994, D50, 760.
7. Brünger, A. T. X-PLOR manual, version 3.1; Yale University Press: New Haven and London, 1992.
8. Brünger, A. T. Acta Crystallogr. 1993, D49, 24. Brünger, A. T. Nature 1992, 355, 472.
9. Brünger, A. T. Acta Crystallogr. 1993, D49, 24. Brünger, A. T. Nature 1992, 355, 472.
10. Jones, T. A.; Zou, J. Y.; Cowan, S. W.; Kjeldgaard, M. Acta Crystallogr. 1991, A47, 110.
11. Jelsch, C.; Mourey, L.; Masson, J. M.; Samama, J. P. Proteins: Struct., Funct., Genet. 1993, 16, 364.
12. Imtiaz, U; Billings, E.; Knox, J. R.; Manavathu, E. K.; Lerner, S. A.; Mobashery, S. J. Am. Chem. Soc. 1993, 115, 4435. Miyashita, K.; Mobashery, S. Bioorg. Med. Chem. Lett. 1995, 5, 1043.
13. Imtiaz, U; Billings, E.; Knox, J. R.; Manavathu, E. K.; Lerner, S. A.; Mobashery, S. J. Am. Chem. Soc. 1993, 115, 4435. Miyashita, K.; Mobashery, S. Bioorg. Med. Chem. Lett. 1995, 5, 1043.
14. Zafaralla, G.; Manavathu, E. K.; Lerner, S. A.; Mobashery, S. Biochemistry 1992, 31, 3847. Imtiaz, U.; Manavathu, E. K.; Lerner, S. A.; Mobashery, S. Antimicrob. Agents Chemother. 1993, 37, 2438. Dubus, A.; Wilkin, J. M.; Raquet, X.; Normark, S.; Frère, J. M. Biochem. J. 1994, 301, 485.
15. Zafaralla, G.; Manavathu, E. K.; Lerner, S. A.; Mobashery, S. Biochemistry 1992, 31, 3847. Imtiaz, U.; Manavathu, E. K.; Lerner, S. A.; Mobashery, S. Antimicrob. Agents Chemother. 1993, 37, 2438. Dubus, A.; Wilkin, J. M.; Raquet, X.; Normark, S.; Frère, J. M. Biochem. J. 1994, 301, 485.
16. Zafaralla, G.; Manavathu, E. K.; Lerner, S. A.; Mobashery, S. Biochemistry 1992, 31, 3847. Imtiaz, U.; Manavathu, E. K.; Lerner, S. A.; Mobashery, S. Antimicrob. Agents Chemother. 1993, 37, 2438. Dubus, A.; Wilkin, J. M.; Raquet, X.; Normark, S.; Frère, J. M. Biochem. J. 1994, 301, 485.
17. Strynadka, N. C. J.; Adachi, H.; Jensen, E. E.; Johns, K.; Sielecki, A.; Betzel, C; Sutoh, K.; James, M. N. G. Nature 1992, 359, 700.
18. Swarén, P.; Maveyraud, L.; Guillet, V.; Masson, J. M.; Mourey, L.; Samama, J. P. Structure 1995, 3, 603.
19. Olovsson, I.; Jönsson, P. G. In The Hydrogen Bond; Schuster, P., Zundel, G., Sandorfy, C., Eds.; North-Holland: Amsterdam, 1976; Vol. 2, pp 393-456.
20. Chen, C. C. H.; Herzberg, O. J. Mol. Biol. 1992, 224, 1103.