Chemoselective ligation applied to the synthesis of a biantennary N-linked glycoform of CD52

Journal of the American Chemical Society

Volumn 125, Issue 20, 2003, Pages 6149-6159

  Pratt, Matthew R ^a   Bertozzi, Carolyn R ^a,b  

^a UNIVERSITY OF CALIFORNIA   (United States)

^b LAWRENCE BERKELEY NATIONAL LABORATORY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALKYLATION; ETHERS; NITROGEN; SACCHARIFICATION; SYNTHESIS (CHEMICAL);

CHEMOSELECTIVE LIGATION;

POLYPEPTIDES;

CD52 ANTIGEN;

ALKYLATION; ARTICLE; PEPTIDE SYNTHESIS; REACTION ANALYSIS;

ANTIGENS, CD; ANTIGENS, NEOPLASM; CARBOHYDRATE SEQUENCE; GLYCOPEPTIDES; GLYCOPROTEINS; MOLECULAR SEQUENCE DATA; OLIGOSACCHARIDES;

EID: 0038627500     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja029346v     Document Type: Article

References (44)

1. (a) Varki, A. Glycobiology 1993, 3, 97-130.
2. (b) Dwek, R. A. Chem. Rev. 1996, 96, 683-720.
3. (a) Bill, R. M.; Revers, L.; Wilson, I. B. H. Protein Glycosylation; Kluwer Academic Publishers: Massachusetts, 1998.
4. (b) Helenius, A.; Aebi, M. Science 2001, 291, 2364-2369.
5. Herzner, H.; Reipen, T.; Schultz, M.; Kunz, H. Chem. Rev. 2000, 100, 4495-4537.
6. (a) Prahl, I.; Unverzagt, C. Tetrahedron Lett. 2000, 41, 10189-10193.
7. (b) Seifert, J.; Unverzagt, C. Tetrahedron Lett. 1996, 37, 6527-6530.
8. (c) Seifert, J.; Unverzagt, C. Tetrahedron Lett. 1997, 38, 7857-7860.
9. (d) Unverzagt, C. Angew. Chem., Int. Ed. Engl. 1994, 33, 1102-1104.
10. (e) Unverzagt, C. Angew. Chem., Int. Ed. Engl. 1996, 35, 2350-2353.
11. (f) Unverzagt, C. Angew. Chem., Int. Ed. Engl. 1997, 36, 1989-1992.
12. (g) Unverzagt, C. Carbohydr. Res. 1997, 305, 423-431.
13. (h) Unverzagt, C. Tetrahedron Lett. 1997, 38, 5627-5630.
14. (i) Danishefsky, S. J.; Hu, S.; Cirillo, P. F.; Eckhardt, M.; Seeberger, P. H. Chem.-Eur. J. 1997, 3, 1617-1628.
15. (j) Wang, Z. G.; Zhang, X. F.; Live, D.; Danishefsky, S. J. Angew. Chem., Int. Ed. 2000, 39, 3652-3656.
16. (k) Wang, Z.-G.; Zhang, X.; Visser, M.; Live, D.; Zatorski, A.; Iserloh, U.; Lloyd, K. O.; Danishefsky, S. J. Angew. Chem., Int. Ed. 2001, 40, 1728-1732.
17. (l) Seifert, J.; Lergenmuller, M.; Ito, Y. Angew. Chem., Int. Ed. 2000, 39, 531-534.
18. Hang, H. C.; Bertozzi, C. R. Acc. Chem. Res. 2001, 34, 727-736.
19. (a) Rodriguez, E. C.; Winans, K. A.; King, D. S.; Bertozzi, C. R. J. Am. Chem. Soc. 1997, 119, 9905-9906.
20. (b) Marcaurelle, L. A.; Rodriguez, E. C.; Bertozzi, C. R. Tetrahedron Lett. 1998, 39, 8417-8420.
21. Marcaurelle, L. A.; Bertozzi, C. R. J. Am. Chem. Soc. 2001, 123, 1587-1595.
22. (a) Treumann, A.; Lifely, M. R.; Schneider, P.; Ferguson, M. A. J. J. Biol. Chem. 1995, 270, 6088-6099.
23. (b) Focarelli, R.; Francavilla, S.; Francavilla, F.; Della Giovampaola, C.; Santucci, A.; Rosati, F. Hum. Reprod. 1999, 5, 46-51.
24. (c) Schröter, S.; Derr, P.; Conradt, H. S.; Nimtz, M.; Hale, G.; Kirchhoff, C. J. Biol. Chem. 1999, 274, 29862-29873.
25. (d) Focarelli, R.; Della Giovampaola, C.; Seraglia, R.; Brettoni, C.; Sabatini, L.; Pescaglini, M.; Rosati, F. Biochem. Biophys. Res. Commun. 1999, 258, 639-643.
26. (a) Guo, Z. W.; Nakahara, Y.; Ogawa, T. Bioorg. Med. Chem. 1997, 5, 1917-1924.
27. (b) Guo, Z. W.; Nakahara, Y.; Ogawa, T. Angew. Chem., Int. Ed. Engl. 1997, 36, 1464-1466.
28. Wyss, D. F.; Choi, J. S.; Li, J.; Knoppers, M. H.; Willis, K. J.; Arulanandam, A. R.; Smolyar, A.; Reinherz, E. L.; Wagner, G. Science 1995, 269, 1273-1278.
29. Imperiali, B.; O'Connor, S. E. Curr. Opin. Chem. Biol. 1999, 3, 643-649.
30. Gunther, W.; Kunz, H. Carbohydr. Res. 1992, 228, 217-241.
31. Deninno, M. P.; Etienne, J. B.; Duplantier, K. C. Tetrahedron Lett. 1995, 36, 669-672.
32. Matsuo, I.; Isomura, M.; Walton, R.; Ajisaka, K. Tetrahedron Lett. 1996, 37, 8795-8798.
33. (a) Gridley, J. J.; Hacking, A. J.; Osborn, H. M. I.; Spackman, D. G. Synlett 1997, 1397-1399.
34. (b) Gridley, J. J.; Hacking, A. J.; Osborn, H. M. I.; Spackman, D. G. Tetrahedron 1998, 54, 14925-14946.
35. van Boeckel, C. A. A.; Beetz, T. Tetrahedron Lett. 1983, 24, 3775-3778.
36. Furstner, A.; Konetzki, I. Tetrahedron Lett. 1998, 39, 5721-5724.
37. Nicolaou, K. C.; Ladduwahetty, J. L. R.; Chucholowski, A. J. Am. Chem. Soc. 1986, 108, 2466-2467.
38. Frick, W.; Bauer, A.; Bauer, J.; Wied, S.; Müller, G. Biochemistry 1998, 37, 13421-13436.
39. King, D. S.; Fields, C. G.; Fields, G. B. Int. J. Pept. Protein Res. 1990, 36, 255-266.
40. Jain, R. K.; Huang, B. G.; Chandrasekaran, E. V.; Matta, K. L. Chem. Commun. 1997, 23-24.
41. Szilagyi, L.; Gyorgydeak, Z. Carbohydr. Res. 1985, 143, 21-41.
42. Bowman, K. G.; Cook, B. N.; de Graffenried, C. L.; Bertozzi, C. R. Biochemistry 2001, 40, 5382-5391.
43. Dankwardt, S. M.; Newman, S. R.; Krstenansky, J. L. Tetrahedron Lett. 1995, 36, 4923-4926.
44. Yuan, C.; Williams, R. M. J. Am. Chem. Soc. 1997, 119, 11777-11784.