Model for antibiotic optimization via neoglycosylation: Synthesis of liponeoglycopeptides active against VRE

Journal of the American Chemical Society

Volumn 129, Issue 26, 2007, Pages 8150-8155

  Griffith, Byron R ^a   Krepel, Candace ^b   Fu, Xun ^a   Blanchard, Sophie ^a   Ahmed, Aqeel ^a   Edmiston, Charles E ^b   Thorson, Jon S ^a  

^a UNIVERSITY OF WISCONSIN MADISON   (United States)

^b MEDICAL COLLEGE OF WISCONSIN   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ANTIBACTERIAL ASSAYS; GLYCOLIPID; NEOGLYCOSYLATION; VANCOMYCIN;

AMINES; GLUCOSE; GLYCOSYLATION; PEPTIDES; STEREOSELECTIVITY; SYNTHESIS (CHEMICAL);

ANTIBIOTICS;

ANTIBIOTIC AGENT; GLUCOPYRANOSIDE; GLYCOPEPTIDE; METHOXYAMINE; ORITAVANCIN; TEICOPLANIN; VANCOMYCIN; VANCOMYCIN DERIVATIVE;

ANTIBACTERIAL ACTIVITY; ARTICLE; BACTERIUM ISOLATE; CHEMICAL REACTION; DRUG POTENCY; DRUG SYNTHESIS; ENTEROCOCCUS FAECALIS; ENTEROCOCCUS FAECIUM; GLYCOSYLATION; HIGH THROUGHPUT SCREENING; LIPIDATION; MINIMUM INHIBITORY CONCENTRATION; NONHUMAN; QUANTUM YIELD; STEREOCHEMISTRY; STEREOISOMERISM; STRUCTURE ACTIVITY RELATION; VANCOMYCIN RESISTANT ENTEROCOCCUS;

ANTI-BACTERIAL AGENTS; ENTEROCOCCUS; GLYCOPEPTIDES; GLYCOSYLATION; MOLECULAR STRUCTURE; VANCOMYCIN RESISTANCE;

EID: 34447255199     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja068602r     Document Type: Article

References (29)

1. Murray, B. E. N. Engl. J. Med. 2000, 342, 710-721.
2. Weigel, L. M.; Clewell, D. B.; Gill, S. R.; Clark, N. C.; McDougal, L. K.; Flannagan, S. E.; Kolonay, J. F.; Shetty, J.; Killgore, G. E.; Tenover, F. C. Science 2003, 302, 1569-1571.
3. Chang, S.; Sievert, D. M.; Hageman, J. C.; Boulton, M. L.; Tenover, F. C.; Downes, F. P.; Shah, S.; Rudrik, J. T.; Pupp, G. R.; Brown, W. J.; Cardo, D.; Fridkin, S. K. N. Engl. J. Med. 2003, 348, 1342-1347.
4. (a) Losey, H. C.; Peczuh, M. W.; Chen, Z.; Eggert, U. S.; Dong, S. D.; Pelczer, I.; Kahne, D.; Walsh, C. T. Biochemistry 2001, 40, 4745-4755.
5. (b) Losey, H. C.; Jiang, J. Q.; Biggins, J. B.; Oberthur, M.; Ye, X. Y.; Dong, S. D.; Kahne, D.; Thorson, J. S.; Walsh, C. T. Chem. Biol. 2002, 9, 1305-1314.
6. (c) Fu, X.; Albermann, C.; Jiang, J. Q.; Liao, J. C.; Zhang, C. S.; Thorson, J. S. Nat. Biotechnol. 2003, 21, 1467-1469.
7. (d) Lin, H. N.; Walsh, C. T. 2004, 126, 13998-14003.
8. (e) Fu, X.; Albermann, C.; Zhang, C. S.; Thorson, J. S. Org. Lett. 2005, 7, 1513-1515.
9. (f) Kruger, R. G.; Lu, W.; Oberthur, M.; Tao, J. H.; Kahne, D.; Walsh, C. T. Chem. Biol. 2005, 12, 131-140.
10. (g) Zhang, C. S.; Griffith, B. R.; Fu, Q.; Albermann, C.; Fu, X.; Lee, I. K.; Li, L. J.; Thorson, J. S. Science 2006, 313, 1291-1294.
11. (a) Allen, N. E.; Nicas, T. I. FEMS Microbiol. Rev. 2003, 26, 511-532.
12. (b) Kahne, D.; Leimkuhler, C.; Wei, L.; Walsh, C. Chem. Rev. 2005, 105, 425-448.
13. Dong, S. D.; Oberthur, M.; Losey, H. C.; Anderson, J. W.; Eggert, U. S.; Peczuh, M. W.; Walsh, C. T.; Kahne, D. J. Am. Chem. Soc. 2002, 124, 9064-9065.
14. Nagarajan, R.; Schabel, A. A.; Occolowitz, J. L.; Counter, F. T.; Ott, J. L.; Feltyduckworth, A. M. J. Antimicrob. Chemother. 1989, 42, 63-72.
15. (a) Peri, F.; Dumy, P.; Mutter, M. Tetrahedron 1998, 54, 12269-12278.
16. (b) Peri, F.; Deutman, A.; La Ferla, B.; Nicotra, F. Chem. Commun. (Cambridge) 2002, 1504-1505.
17. (c) Peri, F.; Jimenez-Barbero, J.; Garcia-Aparicio, V.; Tvaroska, I.; Nicotra, F. Chem.-Eur. J. 2004, 10, 1433-1444.
18. (a) Griffith, B. R.; Langenhan, J. M.; Thorson, J. S. Curr. Opin. Biotechnol. 2005, 16, 622-630.
19. (b) Langenhan, J. M.; Peters, N. R.; Guzei, I. A.; Hoffman, F. M.; Thorson, J. S. Proc. Natl. Acad. Sci. U.S.A. 2005, 102, 12305-12310.
20. (c) Ahmed, A.; Peters, N. R.; Fitzgerald, M. K.; Watson, J. A., Jr.; Hoffman, F. M.; Thorson, J. S. J. Am. Chem. Soc. 2006, 128, 14224-14225.
21. Sun, B.; Chen, Z.; Eggert, U. S.; Shaw, S. J.; LaTour, J. V.; Kahne, D. J. Am. Chem. Soc. 2001, 123, 12722-12723.
22. Thompson, C.; Ge, M.; Kahne, D. J. Am. Chem. Soc. 1999, 121, 1237-1244.
23. See the Supporting Information.
24. Kerns, R.; Dong, S. D.; Fukuzawa, S.; Carbeck, J.; Kohler, J.; Silver, L.; Kahne, D. J. Am. Chem. Soc. 2000, 122, 12608-12609.
25. Thayer, D. A.; Wong, C.-H. Chem. Asian J. 2006, 1, 445-452.
26. Kruger, R. G.; Lu, W.; Oberthur, M.; Tao, J.; Kahne, D.; Walsh, C. T. Chem. Biol. 2005, 12, 131-140.
27. Leimkuhler, C.; Chen, L.; Barrett, D.; Panzone, G.; Sun, B. Y.; Falcone, B.; Oberthur, M.; Donadio, S.; Walker, S.; Kahne, D. J. Am. Chem. Soc. 2005, 127, 3250-3251.
28. (a) Daniel, R. A.; Errington, J. Cell, 2003, 113, 767-776.
29. (b) Tiyanont, K.; Doan, T.; Lazarus, M. B.; Fang, X.; Rudner, D. Z.; Walker, S. Proc. Natl. Acad. Sci. U.S.A. 2006, 103, 11033-11038.