La3+-Catalyzed Methanolysis of N-Aryl-β-lactams and Nitrocefin

Inorganic Chemistry

Volumn 42, Issue 26, 2003, Pages 8624-8632

  Montoya Pelaez, Pedro J ^a   Gibson, Graham T T ^a   Neverov, Alexei A ^a   Brown, R S ^a  

^a QUEEN S UNIVERSITY   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

3,5 DINITROBENZOIC ACID; BENZOIC ACID DERIVATIVE; BETA LACTAM DERIVATIVE; BUFFER; DIMER; LANTHANUM; METAL ION; METHANOL; METHOXIDE; N 4 NITROPHENYL BETA LACTAM; N PHENYL BETA LACTAM; NITROCEFIN; OXIDE; UNCLASSIFIED DRUG; BETA LACTAM; CATION; CEPHALOSPORIN DERIVATIVE;

ARTICLE; CATALYSIS; DECOMPOSITION; ENZYME KINETICS; KINETICS; METHANOLYSIS; POTENTIOMETRY; TITRIMETRY; CHEMISTRY; PH;

BETA-LACTAMS; CATALYSIS; CATIONS; CEPHALOSPORINS; HYDROGEN-ION CONCENTRATION; KINETICS; LANTHANUM; METHANOL; POTENTIOMETRY;

EID: 0345772341     PISSN: 00201669     EISSN: None     Source Type: Journal    
DOI: 10.1021/ic0302736     Document Type: Article

References (56)

1. (a) Neu, H. C. In The Chemistry of β-Lactams; Page, M. I., Ed.; Blackie: Glasgow, U.K., 1992; pp 192-128.
2. (b) Page, M. I. Adv. Phys. Org. Chem. 1987, 23, 165.
3. (a) Page, M. I. Acc. Chem. Res. 1984, 17, 144.
4. (b) Davies, J. Science 1994, 264, 375.
5. (c) Massova, I.; Mobashery, S. Acc. Chem. Res. 1997, 30, 162.
6. Payne, D. J. J. Med. Microbiol. 1993, 39, 93.
7. (a) Lipscomb, W. N.; Sträter, N. Chem. Rev. 1996, 96, 2375 and references therein.
8. (b) Cricco, J. A.; Orellano, E. G.; Rasia, R. M.; Ceccarelli, E. A.; Vila, A. J. Coord. Chem. Rev. 1999, 190-192, 519.
9. (c) Concha, N. O.; Janson, C. A.; Rowling, P.; Pearson, S.; Cheever, C. A.; Clarke, B. P.; Lewis, C.; Galleni, M.; Frère, J.-M.; Payne, D. J.; Bateson, J. H.; Abdel-Meguid, S. S. Biochemistry 2000, 39, 4288.
10. (d) Ullah, J. H.; Walsh, T. R.; Taylor, I. A.; Emery, D. C.; Verma, C. S.; Gamblin, S. J.; Spencer, J. J. Mol. Biol. 1998, 284, 125.
11. (e) Fabiane, S. M.; Sohi, M. K.; Wan, T.; Payne, D. J.; Bateson, J. H.; Mitchell, T.; Sutton, B. J. Biochemistry 1998, 37, 12404.
12. (f) Concha, N. O.; Rasmussen, B. A.; Bush, K.; Herzberg, O. Structure 1996, 4, 823.
13. (a) Bicknell, R.; Schäffer, A.; Walley, S. G.; Auld, D. S. Biochemistry 1986, 25, 7208.
14. (b) Bounaga, S.; Laws, A. P.; Gallei, M.; Page, M. I. Biochem. J. 1998, 331, 703.
15. (c) Page, M. I.; Laws, A. P. J. Chem. Soc., Chem. Commun. 1998, 1609.
16. (a) Wang, Z.; Fast, W.; Benkovic, S. J. Biochemistry 1999, 38, 10013.
17. (b) Fast, W.; Wang, Z.; Benkovic, S. J. Biochemistry 2001, 40, 1640.
18. (c) McManus-Munoz, S.; Crowder, M. W. Biochemistry 1999, 38, 1547.
19. Sabath, L. B.; Abraham, E. P. Biochem. J. 1966, 98, 11c.
20. Wilcox, D. E. Chem. Rev. 1996, 96, 2435.
21. (a) Cressman, W. A.; Sugita, E. T.; Doluiso, J. T.; Niebergall, P. J. J. Pharm. Sci. 1969, 58, 1471.
22. (b) Gensmantel, N. P.; Gowling, E. W.; Page, M. I. J. Chem. Soc., Perkin Trans. 2 1978, 335.
23. (c) Gensmantel, N. P.; Proctor, P.; Page, M. I. J. Chem. Soc., Perkin Trans. 2 1980, 1725.
24. Martinez, J. H.; Navarro, P. G.; Garcia, A. A. M.; de las Parras, P. J. M. Int. J. Biol. Macromol. 1999, 25, 337.
25. (a) Kaminskaia, N. V.; He, C.; Lippard, S. J. Inorg. Chem. 2000, 39, 3365.
26. (b) Kaminskaia, N. V.; Spingler, B.; Lippard, S. J. J. Am. Chem. Soc. 2000, 122, 6411.
27. (c) Kaminskiaia, N.; Spingler, B.; Lippard, S. J. J. Am. Chem. Soc. 2001, 123, 6555.
28. Montoya-Pelaez, P. J.; Brown, R. S. Inorg. Chem. 2002, 41 309-316.
29. Brown, R. S.; Neverov, A. A. J. Chem. Soc., Perkin Trans. 2 2002, 1039.
30. (a) Neverov, A. A.; Brown, R. S. Can. J. Chem. 2000, 78, 1247.
31. (b) Neverov, A. A.; McDonald, T.; Gibson, G.; Brown, R. S. Can. J. Chem. 2001, 79, 1704.
32. (c) Neverov, A. A.; Brown, R. S. Inorg. Chem. 2001, 40, 3588.
33. (d) Tsang, J.; Neverov, A. A.; Brown, R. S. J. Am. Chem. Soc. 2003, 125, 1559.
34. (e) Tsang, J.; Neverov, A. A.; Brown, R. S. J. Am. Chem. Soc. 2003, 125, 7602.
35. (a) Manhas, M.; Jeng, S. J. Org. Chem. 1967, 32, 1246.
36. (b) Blackburn, G.; Plackett, J. J. Chem. Soc., Perkin Trans. 2 1972, 1366.
37. spH is used.
38. (a) Bosch, E.; Rived, F.; Roses, M.; Sales, J. J. Chem. Soc., Perkin Trans. 2 1999, 1953.
39. (b) Rived, F.; Rosés, M.; Bosch, E. Anal. Chim. Acta 1998, 374, 309.
40. (c) Bosch, E.; Bou, P.; Allemann, H.; Roses, M. Anal. Chem. 1996, 3651.
41. Gans, P.; Sabatini, A.; Vacca, A. Talanta 1996, 43, 1739.
42. Gibson, G.; Neverov, A. A.; Brown, R. S. Can. J. Chem. 2003, 81, 495.
43. Harned, H. S.; Owen, B. B. The Physical Chemistry of Electrolytic Solutions, 3rd ed.; ACS Monograph Series 137; Reinhold Publishing: New York, 1957; p 161.
44. Morrow, J. R.; Buttrey, L. A.; Berback, K. A. Inorg. Chem. 1992, 31, 16.
45. Broxton, T. J.; Deady, L. W. J. Org. Chem. 1974, 39, 2767.
46. -1, respectively.
47. (a) Williams, N. H.; Cheung, W.; Chin, J. J. Am. Chem. Soc. 1998, 120, 8079.
48. (b) Wahnon, D. Lebuis, A.-M.; Chin, J. Angew. Chem., Int. Ed. Engl. 1995, 34, 2412.
49. 2+ enzymes and theoretical analyses of such have also considered an opening of the μ-hydroxo bridge prior to nucleophilic attack on bound substrate. Bennett, B.; Holz, R. C. J. Am. Chem. Soc. 1997, 119, 9, 1923. Zhan, C. G.; deSouza, O. N.; Rittenhouse, R.; Ornstein, R. L. J. Am. Chem. Soc. 1999, 121, 7279. Suárez, D.; Brothers, E. N.; Merz, K. M., Jr. Biochemistry 2002, 41, 6615. Diáz, N.; Suárez, D.; Merz, K. M., Jr. J. Am. Chem. Soc. 2000, 120, 4197. Krauss, M.; Gilson, H. R. S.; Gresh, N. J. Phys. Chem. B 2001, 105, 8040.
50. 2+ enzymes and theoretical analyses of such have also considered an opening of the μ-hydroxo bridge prior to nucleophilic attack on bound substrate. Bennett, B.; Holz, R. C. J. Am. Chem. Soc. 1997, 119, 9, 1923. Zhan, C. G.; deSouza, O. N.; Rittenhouse, R.; Ornstein, R. L. J. Am. Chem. Soc. 1999, 121, 7279. Suárez, D.; Brothers, E. N.; Merz, K. M., Jr. Biochemistry 2002, 41, 6615. Diáz, N.; Suárez, D.; Merz, K. M., Jr. J. Am. Chem. Soc. 2000, 120, 4197. Krauss, M.; Gilson, H. R. S.; Gresh, N. J. Phys. Chem. B 2001, 105, 8040.
51. 2+ enzymes and theoretical analyses of such have also considered an opening of the μ-hydroxo bridge prior to nucleophilic attack on bound substrate. Bennett, B.; Holz, R. C. J. Am. Chem. Soc. 1997, 119, 9, 1923. Zhan, C. G.; deSouza, O. N.; Rittenhouse, R.; Ornstein, R. L. J. Am. Chem. Soc. 1999, 121, 7279. Suárez, D.; Brothers, E. N.; Merz, K. M., Jr. Biochemistry 2002, 41, 6615. Diáz, N.; Suárez, D.; Merz, K. M., Jr. J. Am. Chem. Soc. 2000, 120, 4197. Krauss, M.; Gilson, H. R. S.; Gresh, N. J. Phys. Chem. B 2001, 105, 8040.
52. 2+ enzymes and theoretical analyses of such have also considered an opening of the μ-hydroxo bridge prior to nucleophilic attack on bound substrate. Bennett, B.; Holz, R. C. J. Am. Chem. Soc. 1997, 119, 9, 1923. Zhan, C. G.; deSouza, O. N.; Rittenhouse, R.; Ornstein, R. L. J. Am. Chem. Soc. 1999, 121, 7279. Suárez, D.; Brothers, E. N.; Merz, K. M., Jr. Biochemistry 2002, 41, 6615. Diáz, N.; Suárez, D.; Merz, K. M., Jr. J. Am. Chem. Soc. 2000, 120, 4197. Krauss, M.; Gilson, H. R. S.; Gresh, N. J. Phys. Chem. B 2001, 105, 8040.
53. 2+ enzymes and theoretical analyses of such have also considered an opening of the μ-hydroxo bridge prior to nucleophilic attack on bound substrate. Bennett, B.; Holz, R. C. J. Am. Chem. Soc. 1997, 119, 9, 1923. Zhan, C. G.; deSouza, O. N.; Rittenhouse, R.; Ornstein, R. L. J. Am. Chem. Soc. 1999, 121, 7279. Suárez, D.; Brothers, E. N.; Merz, K. M., Jr. Biochemistry 2002, 41, 6615. Diáz, N.; Suárez, D.; Merz, K. M., Jr. J. Am. Chem. Soc. 2000, 120, 4197. Krauss, M.; Gilson, H. R. S.; Gresh, N. J. Phys. Chem. B 2001, 105, 8040.
54. (a) Fersht, A. Enzyme Structure and Mechanism; W. H. Freeman and Co.: New York, 1985; pp 147-8.
55. (b) Eigen, M.; De Maeyer, L. Z. Electrochem. 1955, 59, 986.
56. Neverov, A. A.; Montoya-Pelaez, P.; Brown, R. S. J. Am. Chem. Soc. 2001, 123, 210.