Solution-phase synthesis with solid-state workup of an O-glycopeptide with a cluster of cancer-related T antigens

Organic Letters

Volumn 7, Issue 16, 2005, Pages 3589-3592

  Shao, Ning ^a   Guo, Zhongwu ^a,b  

^a CASE WESTERN RESERVE UNIVERSITY   (United States)

^b WAYNE STATE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

AMINO ACID; ASIALOGLYCOPHORIN AM; ASIALOGLYCOPROTEIN; GLYCOPEPTIDE; TUMOR ANTIGEN;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; SYNTHESIS;

AMINO ACIDS; ANTIGENS, TUMOR-ASSOCIATED, CARBOHYDRATE; ASIALOGLYCOPROTEINS; GLYCOPEPTIDES; MOLECULAR STRUCTURE;

EID: 23944432865     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol0514193     Document Type: Article

References (38)

1. Kunz, H. Pure Appl. Chem. 1993, 65, 1223-1232.
2. Wen, S.; Guo, Z. Org. Lett. 2001, 3, 3773-3776.
3. Xue, J.; Guo, Z. J. Org. Chem. 2003, 68, 2713-2720.
4. Guo, Z.; Nakahara, Y.; Nakahara, Y.; Ogawa, T. Carbohydr. Res. 1997, 303, 373-378.
5. Kunz, H.; Unverzagt, C. Angew. Chem., Int. Ed. Engl. 1988, 27, 1697-1699.
6. Shao, N.; Xue, J.; Guo, Z. J. Org. Chem. 2003, 68, 9003-9011.
7. Tomita, M.; Marchesi, V. T. Proc. Natl. Acad. Sci. U.S.A. 1975, 72, 2964-2968.
8. Springer, G. F.; Desai, P. R.; Banatwala, I. J. Natl. Cancer Inst. 1975, 54, 335-339.
9. Dausset, J.; Moullec, J.; Bernard, J. Blood 1959, 14, 1079-1093.
10. Springer, S. Science 1984, 224, 1198.
11. Kunz, H.; Birnbach, S. Angew. Chem., Int. Ed. Engl. 1986, 25, 360-363.
12. Kunz, H.; Birnbach, S. Carbohydr. Res. 1990, 202, 207-223.
13. Kuduk, S. D.; Schwarz, J. B.; Chen, X.; Glunz, P. W.; Sames, D.; Ragupathi, G.; Livingston, P. O.; Danishefsky, S. J. J. Am. Chem. Soc. 1998, 120, 12474-12485.
14. Klich, G.; Paulsen, H.; Meyer, B.; Meldal, M.; Bock, K. Carbohydr. Res. 1997, 299, 33-48.
15. See review: Nakahara, Y. Trends Glycosci. Glycotechnol. 2003, 15, 257-273.
16. (a) Bencomo, V. V.; Sinay, P. Glycoconjugate J. 1984, 1, 5-8.
17. (b) Ferrari, B.; Pavia, A. A. Tetrahedron 1985, 41, 1939-1944.
18. (c) Paulsen, H.; Merz, G.; Peters, S.; Weichert, U. Liebigs Ann. Chem. 1990, 1165-1173.
19. (d) Nakahara, Y.; Iijima, H.; Sibayama, S.; Ogawa, T. Tetrahedron Lett. 1990, 31, 6897-6900.
20. (e) Ciommer, M.; Kunz, H. Synlett 1991, 593-595.
21. (f) Nakahara, Y.; Iijima, H.; Shibayama, S.; Ogawa, T. Carbohydr. Res. 1991, 216, 211-225.
22. (g) Iijima, H.; Nakahara, Y.; Ogawa, T. Tetrahedron Lett. 1992, 33, 7907-7910.
23. (h) Nakahara, Y.; Iijima, H.; Ogawa, T. Tetrahedron Lett. 1994, 35, 3321-3324.
24. (i) Klich, G.; Paulsen, H.; Meyer, B.; Meldal, M.; Bock, K. Carbohydr. Res. 1997, 299, 33-48.
25. (j) Schwarz, J. B.; Kuduk, S. D.; Chen, X.; Sames, D.; Glunz, P. W.; Danishefsky, S. J. J. Am. Chem. Soc. 1999, 121, 2662-2673.
26. (k) Ando, S.; Nakahara, Y.; Ito, Y.; Ogawa, T. Carbohydr. Res. 2000, 329, 773-780.
27. See review: Arsequell, G.; Valencia, G. Tetrahedron: Asymmetry 1997, 8, 2839-2876.
28. Herzner, H.; Reipen, T.; Schultz, M.; Kunz, H. Chem. Rev. 2000, 100, 4495-4537.
29. Seitz, O. ChemBioChem 2000, 1, 214-246 and references therein.
30. Davis, B. G. Chem. Rev. 2002, 102, 579-601.
31. Lemieux, R.; Ratcliffe, R. M. Can. J. Chem. 1979, 57, 1244-1251.
32. Schmidt, R. R.; Kinzy, W. Adv. Carbohydr. Chem. Biochem. 1994, 50, 21-56.
33. Suzuki, K.; Maeta, H.; Matsumoto, T. Tetrahedron Lett. 1989, 30, 4853-4856.
34. Suzuki, K.; Maeta, H.; Matsumoto, T.; Tsuchihashi, G. Tetrahedron Lett. 1988, 29, 3571-3574.
35. Nakahara, Y.; Nakahara, Y.; Ogawa, T. Carbohydr. Res. 1996, 292, 71-81.
36. Rosen, T.; Lico, I. M.; Chu, D. T. W. J. Org. Chem. 1988, 53, 1580-1582.
37. Shangguan, N.; Katukojvala, S.; Greenberg, R.; Williams, L. J. J. Am. Chem. Soc. 2003, 125, 7754-7755.
38. Fazio, F.; Wong, C.-H. Tetrahedron Lett. 2003, 44, 9083-9085.