Reexamination of neomycin B degradation: Efficient preparation of its CD and D rings as protected glycosyl donors

Organic Letters

Volumn 4, Issue 20, 2002, Pages 3455-3458

  Wu, Baogen ^a,b   Yang, Jun ^a   He, Yun ^a,b   Swayze, Eric E ^a  

^a ISIS PHARMACEUTICALS   (United States)

^b GNF   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ANTIINFECTIVE AGENT; BACTERIAL RNA; FRAMYCETIN; GLYCOL;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; DRUG STABILITY; ENZYME SPECIFICITY; GLYCOSYLATION; METABOLISM; SYNTHESIS;

ANTI-BACTERIAL AGENTS; DRUG STABILITY; FRAMYCETIN; GLYCOLS; GLYCOSYLATION; MOLECULAR STRUCTURE; RNA, BACTERIAL; SUBSTRATE SPECIFICITY;

EID: 0037015423     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol026548n     Document Type: Article

References (37)

1. (a) Tor, Y. Angew. Chem., Int. Ed. 1999, 38, 1579.
2. (b) Hermann, T. Angew. Chem., Int. Ed. 2000, 39, 1890.
3. (c) Sucheck, S. J.; Wong, C.-H. Curr. Opin. Chem. Biol. 2000, 4, 678.
4. (a) Moore, P. B. Annu. Rev. Biochem. 1999, 67, 287.
5. (b) Batey, R. T.; Rambo, R. P.; Doudna, I. A. Angew. Chem., Int. Ed. 1999, 38, 2326.
6. (b) Hermann, T.; Patel, D. J. J. Mol. Biol. 1999, 294, 829.
7. (a) Von Ahsen, U.; Davies, J.; Schreder, R. Nature 1991, 353, 368.
8. (b) Von Ahsen, U.; Davies, J.; Schroeder, R. J. Mol. Biol. 1992, 226, 935.
9. Stage, T. K.; Hertel, K. J.; Uhlenbeck, O. C. RNA 1995, 1, 95.
10. (a) Rogers, J.; Chang, A. H.; Von Ahsen, U.; Schroeder, R.; Davies, J. J. Mol. Biol. 1996, 259, 916.
11. (b) Chia, J.-S.; Wu, H.-L.; Wang, H.-W.; Chen, D.-S.; Chen, P.-J. J. Biomed. Sci. 1997, 4, 208.
12. (a) Moazed, D.; Noller, H. F. Nature 1987, 327, 389.
13. (b) Purohit, P.; Stem, S. Nature 1994, 370, 650.
14. (c) Formy, D.; Recht, M. I.; Blanchard, S. C.; Puglisi, J. D. Science 1996, 1367.
15. (a) Griffey, R. H.; Greig, M. J. H.; An, H.; Sasmor, S.; Manalili, S. J. Am. Chem. Soc. 1999, 121, 474.
16. (b) Griffey, R. H.; Hofstadler, S. A.; Sannes-Lowery, K. A.; Ecker, S. T.; Crooke, S. T. Proc. Natl. Acad. Sci. U.S.A. 1999, 96, 10129.
17. Hendrix, M.; Priestley, E. S.; Joyce, G. F.; Wong, C.-H. J. Am. Chem. Soc. 1997, 119, 3641.
18. (a) Sucheck, S. J.; Wong; A. L.; Koeller, K. M.; Boehr, D. D.; Draker, K.; Sears, P.; Wright, G. D.; Wong, C.-H. J. Am. Chem. Soc. 2000, 122, 5230.
19. (b) Sucheck, S. J.; Greenberg, W. A.; Tolbert, T. J.; Wong, C.-H. Angew. Chem., Int. Ed. 2000, 39, 1080.
20. (c) Greenberg, W. A.; Priestley, E. S.; Sears, P. S.; Alper, P. B.; Rosenbohm, C.; Hendrix, M.; Hung, S. C.; Wong, C.-H. J. Am. Chem. Soc. 1999, 121, 6527.
21. (d) Wong, C.-H.; Hendrix, M.; Manning, D. D.; Rosenbohm, C.; Greenberg, W. A. J. Am. Chem. Soc. 1998, 120, 8319.
22. (e) Alper, P. B.; Hendrix, M.; Sears, P.; Wong, C.-H. J. Am. Chem. Soc. 1998, 120, 1965.
23. (a) Luedtke, N. W.; Baker, T. J.; Goodman, M.; Tor, Y. J. Am. Chem. Soc. 2000, 122, 12035.
24. (b) Kirk, S. R.; Luedtke, N. W.; Tor, Y. J. Am. Chem. Soc. 2000, 122, 980.
25. (c) Michael, K.; Wang, H.; Tor, Y. Bioorg. Med. Chem. 1999, 7, 1361.
26. (d) Wang, H.; Tor, Y. Angew. Chem., Int. Ed. Engl. 1998, 37, 109.
27. (e) Wang, H.; Tor, Y. Bioorg. Med. Chem. Lett. 1997, 7, 1951.
28. (f) Tok, J. B.-H.; Fenker, J. Bioog. Med. Chem. Lett. 2001, 11, 2987.
29. (g) Hamasaki, K.; Ueno, A. Bioog. Med. Chem. Lett. 2001, 11, 591.
30. (h) Hanessian, S.; Tremblay, M.; Kornienko, A.; Moitessier, N. Tetrahedron 2001, 57, 3255.
31. (i) Hamasaki, K.; Woo, M.-W.; Ueno, A. Tetrahedron Lett. 2000, 41, 8327.
32. Ding, D.; Hofstadler, S. A.; Swayze, E. E.; Griffey, R. H. Org. Lett. 2001, 3, 1621.
33. (a) Umezawa, S., Tsuchiya, T. In Aminoglycoside Antibiotics; Humezawa, H., Hooper, I. R., Eds.; Springer-Verlag: Berlin, Heidelberg, New York, 1982; pp 37-110.
34. (b) See refs 9-11 and references therein.
35. (a) Ding. Y.; Swayze, E. E.; Hofstadler, S. A.; Griffey, R. H. Tetrahedron Lett. 2000, 41, 4049.
36. (b) Rinehart, K. L., Jr. The Neomycins and Related Antibiotics; John Wiley and Sons: New York, 1964; pp 93-97.
37. Lahmann, M., Oscarson, S. Org. Lett. 2000, 2, 3881.