Reaction mechanism of the acyl-enzyme formation in β-lactam hydrolysis by means of quantum chemical modeling

Journal of Molecular Structure: THEOCHEM

Volumn 504, Issue 1-3, 2000, Pages 13-28

  Alvarez Idaboy, J R ^a,b   Gonzalez Jonte R ^a,b   Hernandez Laguna A ^c   Smeyers, Y G ^a  

^a INSTITUTO DE ESTRUCTURA DE LA MATERIA   (Spain)

^b UNIVERSITY OF HAVANA   (Cuba)

^c CSIC   (Spain)

Author keywords

PBP's interaction with the lactam antibiotics; Quantum chemical calculations; Lactam antibiotics

Indexed keywords

BETA LACTAM ANTIBIOTIC; BETA LACTAMASE;

ACYLATION; ARTICLE; CHEMICAL ANALYSIS; DRUG HYDROLYSIS; MOLECULAR MODEL; QUANTUM MECHANICS; REACTION ANALYSIS;

EID: 0343526799     PISSN: 01661280     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0166-1280(00)00351-1     Document Type: Article

References (55)

1. Frère J.-M., Joris B. Crit. Rev. Microbiol. 11:1985;299-396.
2. Herzberg O., Moult J. Curr. Opin. Struct. Biol. 1:1991;946-953.
3. Ghuysen J.-M.A. Rev. Microbiol. 45:1991;37-67.
4. Strynadka N.C.J., Adachi H., Jensen S.E., Johns K., Sielecki A., Betzel C., Sutoh K., James M.N.G. Nature. 359:1992;700-705.
5. Saves I., Burlet-Schiltz O., Maveyraud L., Samama J.P., Promé J.C., Masson J.M. Biochemistry. 34:1995;11 660-11 667.
6. Escobar W.A., Tan A.K., Lewis E.R., Fink A.L. Biochemistry. 33:1994;7619-7626.
7. Fink A.L. Chemtracts - Biochem. Mol. Biol. 3:1992;395-399.
8. Lenfant F., Labia R., Masson J.M. J. Biol. Chem. 266:1991;17 187-17 194.
9. Herzberg O., Moult J. Science. 236:1987;694-701.
10. Chen C.C., Smith T.J., Kapadia G., Wäsh S., Zawadzke L.E., Coulson A., Herzberg O. Biochemistry. 35:1996;12 251-12 258.
11. Viadiu H., Osuna J., Fink A.L., Soberón X.T. J. Biol. Chem. 270:1995;781-787.
12. Lenfant F., Petit A., Labia R., Maveyraud L., Samama J.P., Masson J.M. Eur. J. Biochem. 217:1993;939-946.
13. Delaire M., Labia R., Samama J.P., Masson J.M. J. Biol. Chem. 267:1992;20 600-20 606.
14. Imtiaz U., Billings E., Knox J.R., Manavathu E.K., Lerner S.A., Mobashery S. J. Am. Chem. Soc. 115:1993;4435-4442.
15. Laws A.P., Layland N.J., Proctor D.G., Page M.I. J. Chem. Soc. Perkins Trans. 2. 1993;17-21.
16. Dubus A., Normark S., Kania M., Page G.P. Biochemistry. 34:1995;7757-7764.
17. Ellerby L.M., Escobar W.A., Fink A.L., Mitchinson C., Wells J.A. Biochemistry. 29:1990;5797-5806.
18. Osuna J., Viadiu H., Fink A.L., Soberón X. J. Biol. Chem. 270:1995;775-780.
19. Bonomo R.A., Dawes C.G., Knox J.R., Shales D.M. Biochim. Biophys. Acta. 1247:1995;113-120.
20. Tamaki M., Nukaga M., Sawai T. Biochemistry. 33:1994;10 200-10 206.
21. Kelly J.A., Dideberg O., Charlier P., Wery J.P., Libert M., Moews P.C., Knox J.R., Duez C., Fraipont Cl., Joris B., Dusart J., Frère J.M., Ghuysen J.-M. Science. 231:1986;1429-1431.
22. Knox J.R., Moews P.C. J. Mol. Biol. 220:1991;435-440.
23. Tsukamoto K., Tachibana K., Yamazaki N., Ishii Y., Ujiie K., Nishida N., Sawai T. Eur. J. Biochem. 188:1990;15-22.
24. Ghuysen J.M. Trends Microbiol. 2:1994;372-380.
25. Dive G., Dehareng D., Ghuysen J.M. J. Am. Chem. Soc. 116:1994;2548-2556.
26. Culot P., et al. Theor. Chim. Acta. 82:1992;189-205.
27. Lamothe-Brasseur J., Dive G., Dideberg O., Charlier P., Freere J.-M., Ghuysen J.-M. Biochem. J. 279:1991;213-221.
28. Matagne A., Lamothe-Brasseur J., Dive G., Knox J.R., Freere J.-M. Biochem. J. 293:1993;607-611.
29. Warshell A. Curr. Opin. Struct. Biol. 2:1992;230-236. (Computer simulations of enzymatic reactions).
30. Escobar W.A., Tan A.K., Fink A.L. Biochemistry. 30:1991;10 783-10 787.
31. Swaren P., Maveyraud L., Guillet V., Masson J.M., Monrey L., Samama J.P. Structure. 3:1995;603-613.
32. Gloss L.M., Kirsch J.F. Biochemistry. 34:1995;3999-4007.
33. Toney M.D., Kirsch J.F. Biochemistry. 32:1993;1471-1479.
34. Sekimoto T., Matsuyama T., Fukui T., Tanizawa K. J. Biol. Chem. 268:1993;27 039-27 045.
35. Hartman F.C., Lee E.H. J. Biol. Chem. 264:1989;11 784-11 789.
36. Schirch D., Delle Frate S., Iurescia S., Angelaccio S., Contestabile R., Bossa F., Schirch V. J. Biol. Chem. 268:1993;23 132-23 138.
37. Hartman F.C., Milanez S., Lee E.H. J. Biol. Chem. 260:1986;13 968-13 975.
38. Gelsema W.J., de Ligny C.L., Viserman G.F. Rec. Trav. Chim. 84:1965;1129-1134.
39. Wladkowski B.D., Chenoweth S.A., Sanders J.N., Krauss M., Stevens W.J. J. Am. Chem. Soc. 119:1997;6423-6431.
40. Madgwick P.J., Waley S.G. Biochem. J. 248:1987;657-662.
41. Lewis E.R., Winterberg K.M., Fink A.L. Proc. Natl Acad. Sci. USA. 94:1997;443-447.
42. Kraut J.A. Rev. Biochem. 46:1977;331-358.
43. Adachi H., Ohta T., Matsuzawa H. J. Biol. Chem. 266:1991;3186-3189.
44. Frau J., Donoso J., Muñoz F., García-Blanco F. J. Mol. Struct.(Theochem). 390:1997;225-254. (see also pp. 255-263).
45. González-Jonte R., Smeyers Y.G., Hernández-Laguna A., Alvarez-Idaboy J.R., Montero L.A. Fol. Chim. Theor. Lat. 20:1992;113-124.
46. Smeyers Y.G., González-Jonte R., Hernández-Laguna A. J. Mol. Struct. (Theochem). 287:1993;261.
47. R. González-Jonte, Doctoral Thesis, Universidad Autónoma de Madrid, 1995.
48. Stewart J.J. J. Comput. Chem. 10:1989;209-220. (see also pp. 221-264).
49. Stewart J.J. J. Comp.-Aided Mol. Design. 4:1990;1-105.
50. Jelsch C., Lenfant F., Masson J.M., Samama J.P. FEBS Lett. 299:1992;135-142. (and references therein).
51. Pitarch J., Ruiz-López M.F., Pascual-Ahuir J.-L., Silla E., Tuñon I. J. Phys. Chem. B. 101:1997;3581-3588.
52. Antonczak S., Ruiz-López M.F., Rivail J.L. J.Am. Chem. Soc. 116:1994;3912-3921.
53. J.J. Stewart, MOPAC, a general molecular orbital package, QCPE program # 455. MOPAC 6.0 Frank J. Seiller Res. Lab., US Force Academy, Colo. SPGS, Co-80840, 1998.
54. Damblon C., Raquet X., Lian L.-Y., Lamotte-Brasseur J., Fonze E., Charlier P., Roberts G.C.K., Frère J.M. Proc. Natl Sci. USA. 93:1996;1147-1152.
55. AMPAC v. 5.0 Graphical User Interfaces (GUI), Semichem Inc.