Vinyl Sulfones: Inhibitors of SrtA, a Transpeptidase Required for Cell Wall Protein Anchoring and Virulence in Staphylococcus aureus

Journal of the American Chemical Society

Volumn 126, Issue 11, 2004, Pages 3404-3405

  Frankel, Brenda A ^a   Bentley, Matthew ^a   Kruger, Ryan G ^a   McCafferty, Dewey G ^a  

^a UNIVERSITY OF PENNSYLVANIA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

1,2 BIS(PHENYLSULFONYL)ETHYLENE; 3,3,3 TRIFLUORO 1 (PHENYLSULFONYL) 1 PROPENE; ANTIINFECTIVE AGENT; CELL MEMBRANE PROTEIN; DIVINYL SULFONE; ENZYME INHIBITOR; ETHYLVINYLSULFONE; GAMMA GLUTAMYLTRANSFERASE; METHYL VINYL SULFONE; PHENYLSTYRYLSULFONE; PHENYLVINYLSULFONE; SULFONE DERIVATIVE; TRANSPEPTIDASE SRTA; TRANSPEPTIDASE SRTA INHIBITOR; UNCLASSIFIED DRUG; VINYL DERIVATIVE; VIRULENCE FACTOR;

ARTICLE; BACTERIAL VIRULENCE; CELL WALL; DRUG ACTIVITY; ENZYME INHIBITION; INHIBITION KINETICS; NONHUMAN; PATHOGENICITY; SEQUENCE ANALYSIS; STAPHYLOCOCCUS AUREUS;

AMINOACYLTRANSFERASES; BACTERIAL PROTEINS; CELL WALL; CYSTEINE ENDOPEPTIDASES; ENZYME INHIBITORS; STAPHYLOCOCCUS AUREUS; SULFONES; VIRULENCE;

EID: 1642304933     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja0390294     Document Type: Article

References (28)

1. Navarre, W. W.; Schneewind, O. Microbiol. Mol. Biol. Rev. 1999, 63 (1), 174-229.
2. Mazmanian, S. K.; Ton-That, H.; Schneewind, O. Mol. Microbiol. 2001, 40 (5), 1049-1057.
3. Mazmanian, S. K.; Liu, G.; Ton-That, H.; Schneewind, O. Science 1999, 285(5428), 760-763.
4. Mazmanian, S. K.; Liu, G.; Jensen, E. R.; Lenoy, E.; Schneewind, O. Proc. Natl. Acad. Sci. U.S.A. 2000, 97 (10), 5510-5515.
5. (a) Bolken, T. C.; Franke, C. A.; Jones, K. F.; Zeller, G. O.; Jones, C. H.; Dutton, E. K.; Hruby, D. E. Infect. Immun. 2001, 69 (1), 75-80.
6. (b) Garandeau, C.; Reglier-Poupet, H.; Dubail, I.; Beretti, J. L.; Berche, P.; Charbit, A. Infect. Immun. 2002, 70 (3), 1382-1390.
7. (c) Bierne, H.; Mazmanian, S. K.; Trost, M.; Pucciarelli, M. G.; Liu, G. ; Dehoux, P.; Jansch, L.; Garcia-del Portillo, F.; Schneewind, O.; Cossart, P. Mol. Microbiol. 2002, 43 (4), 869-881.
8. (d) Lee, S. F.; Boran, T. L. Infect. Immun. 2003, 71 (2), 676-681.
9. (e) Kharat, A. S.; Tomasz, A. Infect. Immun. 2003, 71 (5), 2758-2765.
10. Alksne, L. E.; Projan, S. J. Curr. Opin. Biotechnol. 2000, 11 (6), 625-636.
11. (a) Mazmanian, S. K.; Ton-That, H.; Su, K.; Schneewind, O. Proc. Natl. Acad. Sci. U.S.A. 2002, 99 (4), 2293-2298.
12. (b) Kruger, R. G.; Otvos, B.; Frankel, B. A.; Bentley, M.; Dostal, P.; McCafferty, D. G. Biochemistry 2004, 43, 1541-1551.
13. (a) Fischetti, V. A.; Pancholi, V.; Schneewind, O. Mol. Microbiol. 1990, 4 (9), 1603-1605.
14. (b) Schneewind, O.; Model, P.; Fischetti, V. A. Cell 1992, 70 (2), 267-281.
15. (a) Ruzin, A.; Severin, A.; Ritacco, F.; Tabei, K.; Singh, G.; Bradford, P. A.; Siegel, M. M.; Projan, S. J.; Shlaes, D. M. J. Bacteriol. 2002, 184 (8), 2141-2147.
16. (b) Perry, A. M.; Ton-That, H.; Mazmanian, S. K.; Schneewind, O. J. Biol. Chem. 2002, 277 (18), 16241-16248.
17. Pallen, M. J.; Lam, A. C.; Antonio, M.; Dunbar, K. Trends Microbiol. 2001, 9 (3), 97-102.
18. Ton-That, H.; Liu, G.; Mazmanian, S. K.; Faull, K. F.; Schneewind, O. Proc. Natl. Acad. Sci. U.S.A. 1999, 96 (22), 12424-12429.
19. (a) Ton-That, H.; Schneewind, O. J. Biol. Chem. 1999, 274 (34), 24316-24320.
20. (b) Ton-That, H.; Mazmanian, S. K.; Alksne, L.; Schneewind, O. J. Biol. Chem. 2002, 277 (9), 7447-7452.
21. (c) Connolly, K. M.; Smith, B. T.; Pilpa, R.; Ilangovan, U.; Jung, M. E. ; Clubb, R. T. J. Biol. Chem. 2003, 24, 24. This reference includes the synthesis of LPAT-vinyl sulfone, which was used as a tool to characterize the ionization of C184 and H120 as a function of pH.
22. (d) Scott, C. J.; McDowell, A.; Martin, S. L.; Lynas, J. F.; Vandenbroeck, K.; Walker, B. Biochem. J. 2002, 366 (Pt 3), 953-958.
23. Huang, X.; Aulabaugh, A.; Ding, W.; Kapoor, B.; Alksne, L.; Tabei, K.; Ellestad, G. Biochemistry 2003, 42 (38), 11307-11315.
24. (a) Hanzlik, R. P.; Thompson, S. A. J. Med. Chem. 1984, 27 (6), 711-712.
25. (b) Palmer, J. T.; Rasnick, D.; Klaus, J. L.; Bromme, D. J. Med. Chem. 1995, 38 (17), 3193-3196.
26. Kruger, R. G.; Dostal, P.; McCafferty, D. G. Anal. Biochem. 2004, 326, 42-48.
27. Kitz, R.: Wilson, I. B. J. Biol. Chem. 1962, 237, 3245-3249.
28. Elgalai, I.; Foster, H. A. J. Appl. Microbiol. 2003, 94 (3), 413-420.