A One-Pot approach to neoglycopeptides using orthogonal native chemical ligation and click chemistry

Organic Letters

Volumn 11, Issue 22, 2009, Pages 5270-5273

  Lee, Dong Jun ^a   Mandai, Kalyaneswar ^b   Harris, Paul W R ^a   Brimble, Margaret A ^a   Kent, Stephen B H ^b  

^a UNIVERSITY OF AUCKLAND   (New Zealand)

^b UNIVERSITY OF CHICAGO   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

GLYCOPEPTIDE; LIGAND;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; COMBINATORIAL CHEMISTRY; KINETICS; STEREOISOMERISM; SYNTHESIS;

COMBINATORIAL CHEMISTRY TECHNIQUES; GLYCOPEPTIDES; KINETICS; LIGANDS; MOLECULAR STRUCTURE; STEREOISOMERISM;

EID: 70749102598     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol902131n     Document Type: Article

References (35)

1. Dwek, R. A. Chem. Rev. 1996, 96, 683-720.
2. Seitz, O. ChemBioChem 2000, 1, 214-246.
3. Brocke, C.; Kunz, H. Biorg. Med. Chem. 2002, 10, 3085-3112.
4. Grogan, M. J.; Pratt, M. R.; Marcaurelle, L. A.; Bertozzi, C. R. Annu. Rev. Biochem. 2002, 71, 593-634.
5. Gamblin, D. P.; Scanlan, E. M.; Davis, B. G. Chem. Rev. 2009, 109, 131-163.
6. Kent, S. B. H. Chem. Soc. Rev. 2009, 38, 338-351.
7. Pratt, M. R.; Bertozzi, C. R. Chem. Soc. Rev. 2005, 34, 58-68.
8. Davis, B. G. Angew. Chem., Int. Ed. 2009, 48, 4674-4678.
9. Specker, D.; Wittmann, V. Top. Curr. Chem. 2007, 267, 65-107.
10. Nicotra, F.; Cipolla, L.; Peri, F.; La Ferla, B.; Redaelli, C. Adv. Carbohydr. Chem. Biochem. 2007, 61, 353-398.
11. Toenpe, C. W.; Christensen, C.; Meldal, M. J. Org. Chem. 2002, 67, 3057-3064.
12. Rostovtsev, V. V.; Green, L. G.; Fokin, V. V.; Sharpless, K. B. Angew. Chem., Int. Ed. 2002, 41, 2596-2599.
13. Huisgen, R. Chem. Ber. 1967, 100, 2494-2507.
14. Huisgen, R. Pure Appl. Chem. 1989, 61, 613-628.
15. Meldal, M.; Tornoe, C. W. Chem. Rev. 2008, 108, 2952-3015.
16. Kolb, H. C.; Sharpless, K. B. Drug Discovery Today 2003, 8, 11281137.
17. Bock, V. D.; Hiemstra, H.; van Maarseveen, J. H. Eur. J. Org. Chem. 2006, 2006, 51-68.
18. Lutz, J. Angew. Chem., Int. Ed. 2007, 46, 1018-1025.
19. Rutjes, F. P. J.; van Delft, F. L.; Blaauw, R. H.; Quaedflieg, P. J. L. M.; Keereweer, A. R.; Groothuys, S.; Kuijpers, B. H. M. Org. Lett. 2004, 6, 3123-3126.
20. Danishefsky, S. J.; Chen, G.; Chen, J.; Wan, Q. J. Org. Chem. 2006, 71, 8244-8249.
21. Walsh, C. T.; Lin, H. J. Am. Chem. Soc. 2004, 126, 13998-14003.
22. For reviews dedicated to click neoglycoconjugates, see; (a) Dondoni, A. Chem. Asian J. 2007, 2, 700-708.
23. (b) Field, R. A.; Nepogodiev, S. A.; Dedola, S. Org. Biomol. Chem. 2007, 5, 1006-1017.
24. Macmillan D.; Blanc, J. Org. Biomol. Chem. 2006, 4, 2847-2850.
25. Macmilla (24) Davis, B. G.; van Kasteren, S. I.; Kramer, H. B.; Gamblin, D. P. Nat. Protocols 2007, 2, 3185-3194.
26. Davis, B. G.; van Kasteren, S. I.; Kramer, H. B.; Jensen, H. H.; Campbell, S. J.; Kirkpatrick, J.; Oldham, N. J.; Anthony, D. C. Nature 2007, 446, 1105-1109.
27. Moroder, L.; Musiol, H.; Dong, S.; Kaiser, M.; Bausinger, R.; Zumbusch, A.; Bertsch, U. ChemBioChem 2005, 6, 625-628.
28. Xiao, J.; Tolbert, T. J. Org. Lett. 2009, 11, 4144-4147.
29. Schnolzer, M.; Alewood, P.; Jones, A.; Alewood, D.; Kent, S. B. H. Int. J. Pept. Res. Ther. 2007, 13, 31-44.
30. Haase, C.; Seitz, O. Top. Curr. Chem. 2007, 267, 1-36.
31. Rose, K.; Vizzavona, J.; Villain, M. Chem. Biol. 2001, 8, 673-679.
32. Bang, D.; Kent, S. B. H. Angew. Chem., Int. Ed. 2004, 43, 2534-2538.
33. Durek, T.; Torbeev, V. Y.; Kent, S. B. H. Proc. Natl. Acad. Sci. 2007, 104, 4846-4851.
34. Johnson, E. C.; Kent, S. B. H. J. Am. Chem. Soc. 2006, 128, 6640-6646.
35. Bang, D.; Pentelute, B. L.; Kent, S. B. H. Angew. Chem., Int. Ed. 2006, 45, 3985-3988.