2005 Alfred Bader Award Lecture Diaminopimelate and lysine biosynthesis - An antimicrobial target in bacteria

Canadian Journal of Chemistry

Volumn 84, Issue 10, 2006, Pages 1197-1207

  Vederas, John C ^a  

^a UNIVERSITY OF ALBERTA   (Canada)

Author keywords

Amino acids; Antibiotics; Aziridines; Enzyme inhibition; Enzyme mechanism

Indexed keywords

AZIRIDINES; BACTERIAL RESISTANCE; ENZYME MECHANISMS;

AMINO ACIDS; ANTIBIOTICS; BIOSYNTHESIS; ENZYME INHIBITION; ENZYMES; PEPTIDES; X RAY CRYSTALLOGRAPHY;

MICROBIOLOGY;

2 (4 AMINO 4 CARBOXYBUTYL)AZIRIDINE 2 CARBOXYLIC ACID; ANTIINFECTIVE AGENT; AZIRIDINE DERIVATIVE; BACTERIAL ENZYME; BACTERIOCIN; BETA LACTAM DERIVATIVE; CARBOXYLIC ACID DERIVATIVE; CYSTEINE; DIAMINOPIMELIC ACID; ENZYME INHIBITOR; EPIMERASE; HYDROGEN; LACTICIN 3147; LANTIBIOTIC; LYSINE; NISIN A; PEPTIDOGLYCAN; POLYPEPTIDE ANTIBIOTIC AGENT; PYRIDOXAL 5 PHOSPHATE; THIOL DERIVATIVE; UNCLASSIFIED DRUG; VANCOMYCIN;

ANTIBIOTIC RESISTANCE; BACTERIAL CELL WALL; BIOSYNTHESIS; CONFERENCE PAPER; DEPROTECTION REACTION; DIASTEREOISOMER; DRUG BINDING; DRUG SYNTHESIS; DRUG TARGETING; ENZYME ACTIVE SITE; ENZYME INHIBITION; ENZYME SPECIFICITY; EPIMERIZATION; HAEMOPHILUS INFLUENZAE; ISOMER; PROTON TRANSPORT; STRUCTURE ACTIVITY RELATION; X RAY CRYSTALLOGRAPHY;

EID: 33847633444     PISSN: 00084042     EISSN: None     Source Type: Journal    
DOI: 10.1139/V06-072     Document Type: Conference Paper

References (43)

1. L.R. Peterson and A. Dalhoff. J. Antimicrob. Chemother. 53, 902 (2004).
2. J.E. McGowan, Jr. Emerging Infect. Dis. 7, 286 (2001).
3. C. Walsh. In Antibiotics, actions, origins, resistance. American Society for Microbiology Press, Washington, D.C. 2003.
4. M. El Ghachi, A. Bouhss, D. Blanot, and D. Mengin-Lecreulx. J. Biol. Chem. 279, 30106 (2004).
5. S.T.D. Hsu, E. Breukink, E. Tischenko, M.A.G. Lutters, B. de Kruijff, R. Kaptein, A.M.J.J. Bonvin, and N.A.J. van Nuland. Nat. Struc. Mol. Biol. 11, 963 (2004).
6. N.L. Rose, P. Sporns, H.M. Dodd, M.J. Gasson, F.A. Mellon, and L.M. McMullen. J. Agric. Food Chem. 51, 3174 (2003).
7. N.I. Martin, T. Sprules, M.R. Carpenter, P.D. Cotter, C. Hill, R.P. Ross, and J.C. Vederas. Biochemistry, 43, 3049 (2004), and refs. cited therein.
8. P.D. Cotter, C. Hill, and R.P. Ross. Curr. Protein Pept. Sci. 6, 61 (2005).
9. J. Van Heijenoort. Nat. Prod. Rep. 18, 503 (2001).
10. R.J. Cox, A. Sutherland, and J.C. Vederas. Bioorg. Med. Chem. 8, 843 (2000).
11. S.D. Abbott, P. Lane-Bell, K.P.S. Sidhu, and J.C. Vederas. J. Am. Chem. Soc. 116, 6513 (1994).
12. D. Mengin-Lecreulx, D. Blanot, and J. van Heijenoort. J. Bacteriol. 176, 4321 (1994).
13. J.S. Wiseman and J.S. Nichols. J. Biol. Chem. 259, 8907 (1984).
14. M.E. Tanner. Acc. Chem. Res. 35, 237 (2002).
15. T. Yoshimura and N. Esaki. J. Biosci. Bioeng. 96, 103 (2003).
16. L. Liu, K. Iwata, A. Kita, Y. Kawarabayasi, M. Yohda, and K. Miki. J. Mol. Biol. 319, 479 (2002).
17. S. Glavas and M.E. Tanner. Biochemistry, 40, 6199 (2001).
18. H. Mobitz and T.C. Bruice. Biochemistry, 43, 9685 (2004).
19. W.J. Albery and J.R. Knowles. Biochemistry, 25, 2572 (1986).
20. C.W. Koo and J.S. Blanchard. Biochemistry, 38, 4416 (1999).
21. Y. Gao, P. Lane-Bell, and J.C. Vederas. J. Org. Chem. 63, 2133 (1998).
22. J.P. Richard and T.L. Amyes. Bioorg. Chem. 32, 354 (2004), and refs. cited therein.
23. J.P. Richard and T.L. Amyes. Curr. Opin. Chem. Biol. 5, 626 (2001).
24. M.H. Gelb, Y. Lin, M.A. Pickard, Y. Song, and J.C. Vederas. J. Am. Chem. Soc. 112, 4932 (1990).
25. C.W. Koo, A. Sutherland, J.C. Vederas, and J.S. Blanchard. J. Am. Chem. Soc. 122, 6122 (2000).
26. M. Cirilli, R. Zheng, G. Scapin, and J.S. Blanchard. Biochemistry, 37, 16452 (1998).
27. A.J. Lloyd, T. Huyton, J. Turkenburg, and D.I. Roper. Acta Crystallogr. Sect. D, Biol. Crystallogr. 60, 397 (2004).
28. M. Anderson. PCT Int. Application (AstraZeneca AB, Sweden, AstraZeneca Pharmaceuticals LP). WO 2004/061097, 1125 pp.
29. E. Puig, M. Garcia-Viloca, A. Gonzalez-Lafont, I. Lopez, X. Daura, and J.M. Lluch. J. Chem. Theory Comput. 1, 737 (2005).
30. F. Gerhart, W. Higgins, C. Tardif, and J.B. Ducep. J. Med. Chem. 33, 2157 (1990).
31. M.E. Tanner and S. Miao. Tetrahedron Lett. 35, 4073 (1994).
32. R.J. Cox, J. Durston, and D.I. Roper. J. Chem. Soc. Perkin Trans. 1, 1029 (2002).
33. J.T. Kapron, B.D. Santarsiero, and J.C. Vederas. J. Chem. Soc. Chem. Commun. 1074 (1993).
34. T.K. Chakraborty and A. Ghosh. Indian J. Chem. Sect. B: Org. Chem. 40, 895 (2001).
35. K.-S. Yang and K. Chen. J. Org. Chem. 66, 1676 (2001).
36. R.S. Atkinson, R.D. Draycott, D.J. Hirst, M.J. Parratt, and T.M. Raynham. Tetrahedron Lett. 43, 2083 (2002).
37. C.M. Diaper, A. Sutherland, B. Pillai, M.N.G. James, P. Semchuk, J.S. Blanchard, and J.C. Vederas. Org. Biomol. Chem. 3, 4402 (2005).
38. D.H.R. Barton, S.D. Gero, B. Quiclet-Sire, and M. Samadi. J. Chem. Soc. Perkin Trans. 1, 981 (1991).
39. P. Gogoi. Synlett, 2263 (2005).
40. S.V. Ley, I.R. Baxendale, R.N. Bream, P.S. Jackson, A.G. Leach, D.A. Longbottom, M. Nesi, J.S. Scott, R.I. Storer, and S.J. Taylor. J. Chem. Soc. Perkin Trans. 1, 3815 (2000).
41. K.L. Kaestle, M.K. Anwer, T.K. Audhya, and G. Goldstein. Tetrahedron Lett. 32, 327 (1991).
42. S.N. Ruzheinikov, M.A. Taal, S.E. Sedelnikova, P.J. Baker, and D.W. Rice. Structure, 13, 1707 (2005).
43. B. Pillai, M.M. Cherney, C.M. Diaper, A. Sutherland, J.S. Blanchard, J.C. Vederas, M.N.G. James, Proc. Natl. Acad. Sci. U.S.A. 103, 8668 (2006).