A chemoenzymatic approach to glycopeptide antibiotics

Journal of the American Chemical Society

Volumn 126, Issue 43, 2004, Pages 13998-14003

  Lin, Hening ^a   Walsh, Christopher T ^a  

^a HARVARD MEDICAL SCHOOL   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ADDITION REACTIONS; CARBOHYDRATES; CATALYSIS; DERIVATIVES; ENZYMES; POLYPEPTIDES;

BIOLOGICAL ACTIVITIES; GLYCOPEPTIDES; MACROCYCLIZATION;

ANTIBIOTICS;

ANTIBIOTIC AGENT; CARBOHYDRATE; COPPER; GLYCOPEPTIDE; PROPARGYLGLYCINE; SYNTHETASE; THIOL ESTER HYDROLASE; TYROCIDINE;

ANTIBACTERIAL ACTIVITY; ARTICLE; CATALYSIS; CYCLOADDITION; HEMOLYSIS; PROTEIN DOMAIN;

ALKYNES; AMINO ACID SEQUENCE; ANTI-BACTERIAL AGENTS; AZIDES; CARBOHYDRATES; CYCLIZATION; GLYCINE; GLYCOPEPTIDES; MICROBIAL SENSITIVITY TESTS; MONOSACCHARIDES;

EID: 7444226365     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja045147v     Document Type: Article

References (33)

1. Ge, M.; Chen, Z.; Onishi, H. R.; Kohler, J.; Silver, L. L.; Kerns, R.; Fukuzawa, S.; Thompson, C.; Kahne, D. Science 1999, 284, 507-511.
2. Trauger, J. W.; Kohli, R. M.; Mootz, H. D.; Marahiel, M. A.; Walsh, C. T. Nature 2000, 407, 215-218.
3. Kohli, R. M.; Walsh, C. T.; Burkart, M. D. Nature 2002, 418, 658-661.
4. Rostovtsev, V. V.; Green, L. G.; Fokin, V. V.; Sharpless, K. B. Angew. Chem., Int. Ed. 2002, 41, 2596-2599.
5. Wang, Q.; Chan, T. R.; Hilgraf, R.; Fokin, V. V.; Sharpless, K. B.; Finn, M. G. J. Am. Chem. Soc. 2003, 125, 3192-3193.
6. Speers, A. E.; Adam, G. C.; Cravatt, B. F. J. Am. Chem. Soc. 4686, 125, 4686-4687.
7. Lee, L. V.; Mitchell, M. L.; Huang, S.-J.; Fokin, V. V.; Sharpless, K. B.; Wong, C.-H. J. Am. Chem. Soc 2003, 125, 9588-9589.
8. Link, A. J.; Tirrell, D. A. J. Am. Chem. Soc. 2003, 125, 11164-11165.
9. Deiters, A.; Cropp, T. A.; Mukherji, M.; Chin, J. W.; Anderson, J. T.; Schultz, P. G. J. Am. Chem. Soc. 2003, 125, 11782-11783.
10. Davis, B. G. Chem. Rev. 2002, 102, 579-601.
11. Grogan, M. J.; Pratt, M. R.; Marcaurelle, L. A.; Bertozzi, C. R. Annu. Rev. Biochem. 2002, 71, 593-634.
12. Solenberg, P. J.; Matsushima, P.; Stack, D. R.; Wilkie, S. C.; Thompson, R. C.; Baltz, R. H. Chem. Biol. 1997, 4, 195-202.
13. Thompson, C.; Ge, M.; Kahne, D. J. Am. Chem. Soc. 1999, 121, 1237-1244.
14. Nicolaou, K. C.; Cho, S. Y.; Hughes, R.; Winssinger, N.; Smethurst, C.; Labischinski, H.; Endermann, R. Chem. Eur. J. 2001, 7, 3798-3823.
15. Losey, H.; Peczuh, M.; Chen, Z.; Eggert, U.; Dong, S.; Pelczer, I.; Kahne, D.; Walsh, C. Biochemistry 2001, 40, 4745-4755.
16. Sun, B.; Chen, Z.; Eggert. U. S.; Shaw, S. J.; LaTour, J. V.; Kahne, D. J. Am. Chem. Soc. 2001, 123, 12722-12723.
17. 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.
18. Ritter, T. K.; Mong, K.-K. T.; Liu, H.; Nakatni, T.; Wong, C.-H. Angew. Chem., Int. Ed. 2003, 42, 4657-4660.
19. Fu, X.; Albermann, C.; Jiang, J.; Liao, J.; Zhang, C.; Thorson, J. S. Nat. Biotechnol. 2003, 21, 1467-1469.
20. Izumiya, N.; Kato, T.; Aoyagi, H.; Waki, M.; Kondo, M. Kondansha International Ltd.: Tokyo, 1979.
21. Lambert, H. P.; O'Grady, F. W. Antibiotic and Chemotherapy, 6th ed.; Churchill Livingstone: Edinburgh, U.K., 1992; pp 232-233.
22. Fazio, F.; Bryan, M. C.; Blixt, O.; Paulson, J. C.; Wong, C. H. J. Am. Chem. Soc. 2002, 124, 14397-14402.
23. Wang, P.; Shen, G. J.; Wang, Y. F.; Ichikawa, Y.; Wong, C. H. J. Org. Chem. 1993, 58, 3985-3990.
24. May, J. A.; Sartorelli, A. C. J. Med. Chem. 1979, 22, 971-976.
25. Maier, M. A.; Yannopoulos, C. G.; Mohamed, N.; Roland, A.; Fritz, H.; Mohan, V.; Just, G.; Manoharan. M. Bioconjugate Chem. 2003, 14, 18-29.
26. Chernyak, A. Y.; Sharma, G. V. M.; Kononov, L. O.; Krishna, P. R.; Levinsky, A. B.; Kochetkov, N. K. Carbohydr. Res. 1992, 223, 303-309.
27. Ni, J.; Singh, S.; Wang, L.-X. Bioconjugate Chem. 2003, 14, 232-238.
28. Roy, R.; Kim, J. M. Tetrahedron 2003, 59, 3881-3893.
29. Kerns, R.; Dong, S. D.; Fukuzawa, S.; Carbeck, J.; Kohler, J.; Silver, L.; Kahne, D. J. Am. Chem. Soc. 2000, 122, 12608-12609.
30. Mammen, M.; Choi, S.-K.; Whitesides, G. M. Angew. Chem., Int. Ed. 1998, 37, 2754-2794.
31. Tseng, C. C.; Bruner, S. D.; Kohli, R. M.; Marahiel, M. A.; Walsh, C. T.; Sieber, S. A. Biochemistry 2002, 41, 13350-13359.
32. Sieber, S. A.; Tao, J.; Walsh, C. T.; Marahiel, M. A. Angew. Chem., Int. Ed. 2004, 43, 493-498.
33. Grunewald, J.; Sieber, S. A.; Marahiel, M. Biochemistry 2004, 43, 2915-2925.