Ramoplanin inhibits bacterial transglycosylases by binding as a dimer to lipid II

Journal of the American Chemical Society

Volumn 125, Issue 29, 2003, Pages 8736-8737

  Hu, Yanan ^a   Helm, Jeremiah S ^a   Chen, Lan ^a   Ye, Xiang Yang ^a   Walker, Suzanne ^a  

^a PRINCETON UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

DIMER; GLYCOSYLTRANSFERASE; LIPID; LIPID II; RAMOPLANIN; UNCLASSIFIED DRUG;

ARTICLE; DRUG ACTIVITY; DRUG STRUCTURE; ENZYME INHIBITION; PROTEIN LIPID INTERACTION; STRUCTURE ANALYSIS;

ANTI-BACTERIAL AGENTS; BACTERIAL OUTER MEMBRANE PROTEINS; BACTERIAL PROTEINS; CARRIER PROTEINS; DEPSIPEPTIDES; DIMERIZATION; DOSE-RESPONSE RELATIONSHIP, DRUG; HEXOSYLTRANSFERASES; KINETICS; MULTIENZYME COMPLEXES; MURAMOYLPENTAPEPTIDE CARBOXYPEPTIDASE; N-ACETYLGLUCOSAMINYLTRANSFERASES; PENICILLIN-BINDING PROTEINS; PEPTIDES, CYCLIC; PEPTIDYL TRANSFERASES; PROTEIN CONFORMATION; URIDINE DIPHOSPHATE N-ACETYLMURAMIC ACID;

EID: 0038298097     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja035217i     Document Type: Article

References (24)

1. (a) Johnson, C. C.; Taylor, S.; Pitsakis, P.; May, P.; Levison, M. E. Antimicrob. Agents Chemother. 1992, 36, 2342-2345.
2. (b) Brumfitt, W.; Salton, M. R. J.; Hamilton-Miller, J. M. T. Antimicrob. Agents Chemother. 2002, 50, 731-734.
3. Genome Therapeutics Corp. is developing ramoplanin.
4. Somner, E. A.; Reynolds, P. E. Antimicrob. Agents Chemother. 1990, 34, 413-419.
5. Helm, J. S.; Chen, L.; Walker, S. J. Am. Chem. Soc. 2002, 124, 13970-13971.
6. Lo, M.-C.; Men, H.; Branstrom, A.; Helm, J.; Yao, N.; Goldman, R.; Walker, S. J. Am. Chem. Soc. 2000, 122, 3540-3541.
7. Strategies to synthesize Lipid II and analogues have enabled assays of transglycosylase activity. See: (a) Ye, X.-Y.; Lo, M.-C.; Brunner, L.; Walker, D.; Kahne, D.; Walker, S. J. Am. Chem. Soc. 2001, 123, 3155-3156. (b) Schwartz, B.; Markwalder, J. A.; Wang, Y. J. Am. Chem. Soc. 2001, 123, 11638-11643. (c) Schwartz, B.; Markwalder, J. A.; Seitz, S. P.; Wang, Y.; Stein, R. L. Biochemistry 2002, 41, 12552-12561. (d) Chen, L.; Walker, D.; Sun, B.; Hu, Y.; Walker, S.; Kahne, D. Proc. Natl. Acad. Sci. U.S.A. 2003, 100, 5658-5663. (e) VanNieuwenhze, M. S.; Mauldin, S. C.; Zia-Ebrahimi, M.; Winger, B. E.; Hornback, W. J.; Saha, S. L.; Aikins, J. A.; Blaszczak, L. C. J. Am. Chem. Soc. 2002, 124, 3656-3660.
8. Strategies to synthesize Lipid II and analogues have enabled assays of transglycosylase activity. See: (a) Ye, X.-Y.; Lo, M.-C.; Brunner, L.; Walker, D.; Kahne, D.; Walker, S. J. Am. Chem. Soc. 2001, 123, 3155-3156. (b) Schwartz, B.; Markwalder, J. A.; Wang, Y. J. Am. Chem. Soc. 2001, 123, 11638-11643. (c) Schwartz, B.; Markwalder, J. A.; Seitz, S. P.; Wang, Y.; Stein, R. L. Biochemistry 2002, 41, 12552-12561. (d) Chen, L.; Walker, D.; Sun, B.; Hu, Y.; Walker, S.; Kahne, D. Proc. Natl. Acad. Sci. U.S.A. 2003, 100, 5658-5663. (e) VanNieuwenhze, M. S.; Mauldin, S. C.; Zia-Ebrahimi, M.; Winger, B. E.; Hornback, W. J.; Saha, S. L.; Aikins, J. A.; Blaszczak, L. C. J. Am. Chem. Soc. 2002, 124, 3656-3660.
9. Strategies to synthesize Lipid II and analogues have enabled assays of transglycosylase activity. See: (a) Ye, X.-Y.; Lo, M.-C.; Brunner, L.; Walker, D.; Kahne, D.; Walker, S. J. Am. Chem. Soc. 2001, 123, 3155-3156. (b) Schwartz, B.; Markwalder, J. A.; Wang, Y. J. Am. Chem. Soc. 2001, 123, 11638-11643. (c) Schwartz, B.; Markwalder, J. A.; Seitz, S. P.; Wang, Y.; Stein, R. L. Biochemistry 2002, 41, 12552-12561. (d) Chen, L.; Walker, D.; Sun, B.; Hu, Y.; Walker, S.; Kahne, D. Proc. Natl. Acad. Sci. U.S.A. 2003, 100, 5658-5663. (e) VanNieuwenhze, M. S.; Mauldin, S. C.; Zia-Ebrahimi, M.; Winger, B. E.; Hornback, W. J.; Saha, S. L.; Aikins, J. A.; Blaszczak, L. C. J. Am. Chem. Soc. 2002, 124, 3656-3660.
10. Strategies to synthesize Lipid II and analogues have enabled assays of transglycosylase activity. See: (a) Ye, X.-Y.; Lo, M.-C.; Brunner, L.; Walker, D.; Kahne, D.; Walker, S. J. Am. Chem. Soc. 2001, 123, 3155-3156. (b) Schwartz, B.; Markwalder, J. A.; Wang, Y. J. Am. Chem. Soc. 2001, 123, 11638-11643. (c) Schwartz, B.; Markwalder, J. A.; Seitz, S. P.; Wang, Y.; Stein, R. L. Biochemistry 2002, 41, 12552-12561. (d) Chen, L.; Walker, D.; Sun, B.; Hu, Y.; Walker, S.; Kahne, D. Proc. Natl. Acad. Sci. U.S.A. 2003, 100, 5658-5663. (e) VanNieuwenhze, M. S.; Mauldin, S. C.; Zia-Ebrahimi, M.; Winger, B. E.; Hornback, W. J.; Saha, S. L.; Aikins, J. A.; Blaszczak, L. C. J. Am. Chem. Soc. 2002, 124, 3656-3660.
11. Strategies to synthesize Lipid II and analogues have enabled assays of transglycosylase activity. See: (a) Ye, X.-Y.; Lo, M.-C.; Brunner, L.; Walker, D.; Kahne, D.; Walker, S. J. Am. Chem. Soc. 2001, 123, 3155-3156. (b) Schwartz, B.; Markwalder, J. A.; Wang, Y. J. Am. Chem. Soc. 2001, 123, 11638-11643. (c) Schwartz, B.; Markwalder, J. A.; Seitz, S. P.; Wang, Y.; Stein, R. L. Biochemistry 2002, 41, 12552-12561. (d) Chen, L.; Walker, D.; Sun, B.; Hu, Y.; Walker, S.; Kahne, D. Proc. Natl. Acad. Sci. U.S.A. 2003, 100, 5658-5663. (e) VanNieuwenhze, M. S.; Mauldin, S. C.; Zia-Ebrahimi, M.; Winger, B. E.; Hornback, W. J.; Saha, S. L.; Aikins, J. A.; Blaszczak, L. C. J. Am. Chem. Soc. 2002, 124, 3656-3660.
12. Segel, I. H. Enzyme Kinetics; John Wiley & Sons: New York, 1975.
13. d of 16 nM for the ramoplanin-Lipid II complex was calculated (Kaleidograph) on the basis of a curve fit to the kinetic data assuming a 2:1 binding stoichiometry and using an equation for substrate depeletion. See ref 7. The data cannot be fit to a 1:1 binding model.
14. Likussar, W.; Boltz, D. F. Anal. Chem. 1971, 43, 1265-1272.
15. Vollmerhaus, P. J.; Breukink, E.; Heck, A. J. R. Chem.-Eur. J. 2003, 9, 1556-1565.
16. (a) Lo, M.-C. Ph. D. Thesis; Princeton University, 2000.
17. (b) Cudic, P.; Kranz, J. K.; Behenna, D. C.; Kruger, R. G.; Tadesse, H.; Wand, A. J.; Veklich, Y. I.; Weisel, J. W.; McCafferty, D. G. Proc. Natl. Acad. Sci. U.S.A. 2002, 99, 7384-7389.
18. McCafferty and co-workers have carried out NMR studies of ramoplanin and Lipid I analogues in a DMSO/water mixture and have reported a 1:1 model for binding. See ref 1 lb.
19. Lo, M.-C.; Helm, J. S.; Sarngadharan, G.; Pelczer, I.; Walker, S. J. Am. Chem. Soc. 2001, 123, 8640-4641.
20. Maplestone, R. A.; Cox, J. P.; Williams, D. H. FEBS Lett. 1993, 326, 95-100.
21. Kurz, M.; Guba, W. Biochemistry 1996, 35, 12570-12575.
22. (a) Jiang, W.; Wanner, J.; Lee, R. J.; Boundaud, P. Y.; Boger, D. L. J. Am. Chem. Soc. 2002, 124, 5288-5290.
23. (b) Jiang, W.; Wanner, J.; Lee, R. J.; Boundaud, P. Y.; Boger, D. L. J. Am. Chem. Soc. 2003, 125, 1877-1887.
24. Clark, T. D.; Buriak, J. M.; Kobayashi, K.; Isler, M. P.; McRee, D. E.; Ghadiri, M. R. J. Am. Chem. Soc. 1998, 120, 8949-8962.