Unprotected oligosaccharides as phase tags: Solution-phase synthesis of glycopeptides with solid-phase workups

Organic Letters

Volumn 3, Issue 23, 2001, Pages 3773-3776

  Wen, Showming ^a   Guo, Zhongwu ^a  

^a CASE WESTERN RESERVE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

DYES, REAGENTS, INDICATORS, MARKERS AND BUFFERS; GLYCOPEPTIDE; OLIGOSACCHARIDE;

ARTICLE; CHEMISTRY; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; SYNTHESIS;

GLYCOPEPTIDES; INDICATORS AND REAGENTS; MAGNETIC RESONANCE SPECTROSCOPY; OLIGOSACCHARIDES;

EID: 0035891719     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol0101988     Document Type: Article

References (34)

1. Varki, A. Glycobiology 1993, 3, 97-130.
2. Dwek, R. A. Chem. Rev. 1996, 96, 683-720.
3. Large, D. G.; Warren, C. D. Glycopeptides and Related Compounds; Marcel Dekker: New York, 1997.
4. Arsequell, G.; Valencia, G. Tetrahedron: Asymmetry 1997, 8, 2839-2876.
5. Osborn, H. M. I.; Khan, T. H. Tetrahedron 1999, 55, 1807-1850.
6. Paulsen, H. Angew. Chem., Int. Ed. Engl. 1990, 29, 823-838.
7. Meldal, M.; Bock, K. Glycoconjugate J. 1994, 11, 59-63.
8. Kunz, H. Pure Appl. Chem. 1993, 65, 1223-1232.
9. Wong, C.-H.; Schuster, M.; Wang, P.; Sears, P. J. Am. Chem. Soc. 1993, 115, 5893-5901.
10. Witte, K.; Seitz, O.; Wong, C.-H. J. Am. Chem. Soc. 1998, 120, 1979-1989.
11. Ogawa, T. Chem. Soc. Rev. 1994, 397-407.
12. Roberge, J. Y.; Beebe, X.; Danishefsky, S. J. J. Am. Chem. Soc. 1998, 120, 3915-3927.
13. Cohen-Anifeld, S.-T.; Lansbury, P. T. J. J. Am. Chem. Soc. 1993, 115, 10531-10537.
14. Mizuno, M.; Haneda, K.; Iguchi, R.; Muramoto, I.: Kawakami, T.; Aimoto, S.; Yamamoto, K.; Inazu, T. J. Am. Chem. Soc. 1999, 121, 284-290.
15. Deras, I. L.; Takegawa, K.; Kondo, A.; Kato, I.; Lee, Y. C. Bioorg. Med. Chem. Lett. 1998, 8, 1763-1766.
16. Witte, K.; Sears, P.; Martin, R.; Wong, C.-H. J. Am. Chem. Soc. 1997, 119, 2114-2118.
17. Schuster, M.; Wang, P.; Paulson, J. C.; Wong, C.-H. J. Am. Chem. Soc. 1994, 116, 1135-1136.
18. Nakahara, Y.; Nakahara, Y.; Ogawa, T. Carbohydr. Res. 1996, 292, 71-81.
19. Bielfeldt, T.; Peters, S.; Meldal, M.; Bock, K.; Paulsen, H. Angew. Chem., Int. Ed. Engl. 1992, 31, 857-859.
20. Guo, Z.; Nakahara, Y.; Nakahara, Y.; Ogawa, T. Angew. Chem., Int. Ed. Engl. 1997, 36, 1464-1467 and references therein.
21. Klich, G.; Paulsen, H.; Meyer, B.; Meldal, M.; Bock, K. Carbohydr. Res. 1997, 299, 33-48.
22. Guo, Z.; Nakahara, Y.; Nakahara, Y.; Ogawa, T. Bioorg. Med. Chem. 1997, 5, 1917-1924 and references therein.
23. Guo, Z.; Nakahara, Y.; Nakahara, Y.; Ogawa, T. Carbohydr. Res. 1997, 303, 373-378.
24. Douglas, S. P.; Whitfield, D. M.; Krepinsky, D. M. J. Am. Chem. Soc. 1991, 113, 5095-5097.
25. Gravert, D.; Janda, K. D. Chem. Rev. 1997, 97, 489-510.
26. Bosanac, T.; Yang, J.; Wilcox, C. S. Angew. Chem., Int. Ed. 2001, 40, 1875-1879.
27. Ley, S. V.; Massi, A.; Rodriguez, F.; Horwell, D. C.; Lewthwaite, R. A.; Pritchard, M. C.; Reid, A. M. Angew. Chem., Int. Ed. 2001, 40, 1053-1055.
28. Perrier, H.; Labelle, M. J. Org. Chem. 1999, 64, 2110-2113.
29. Hay, A. M.; Hobbs-Dewitt, S.; MacDonald, A. A.; Ramage, R. Tetrahedron Lett. 1998, 39, 8721-8724.
30. (a) Studer, A.; Hadida, S.; Ferritto, R.; Kim, S.; Jeger, P.; Wipf, P.; Curran, D. P. Science 1997, 275, 823-826.
31. (b) Curran, D. P. Angew. Chem., Int. Ed. 1998, 37, 1174-1196.
32. Xia, M.-Q.; Hale. G.; Lifely, M. R.; Ferguson, M. A. J.; Capmbell, D.; Packman, L.; Waldmann, H. Biochem. J. 1993, 293, 633-640.
33. Treumann, A.; Lifely, M. R.; Schneider, P.; Ferguson, M. A. J. J. Biol. Chem. 1995, 270, 6088-6099.
34. Otvos, L. J.; Urge, L.; Hollosi, M.; Wroblewski, K.; Graczyk, G.; Fasman, G. D.; Thurin, J. Tetrahedron Lett. 1990, 31, 5889-5892.