Solid-phase synthesis and conformational studies of helper T cell immunogenic peptides that carry carbohydrate haptens linked to serine

International Journal of Peptide and Protein Research

Volumn 47, Issue 5, 1996, Pages 340-347

  Elofsson, Mikael ^a   Walse, Björn ^a   Kihlberg, Jan ^a  

^a LUND INSTITUTE OF TECHNOLOGY   (Sweden)

Author keywords

conformational studies; glycosylated amino acids; helper T cell; immunogenic glycopeptide; solid phase glycopeptide synthesis

Indexed keywords

ANTIGEN; DIMETHYL SULFOXIDE; GLYCOPEPTIDE; HAPTEN; LYSOZYME; SYNTHETIC PEPTIDE;

ARTICLE; HELPER CELL; IMMUNOGENICITY; PEPTIDE SYNTHESIS; PROTEIN CONFORMATION; PROTEIN GLYCOSYLATION; PROTON NUCLEAR MAGNETIC RESONANCE; STEREOCHEMISTRY;

EID: 0029989839     PISSN: 03678377     EISSN: None     Source Type: Journal    
DOI: 10.1111/j.1399-3011.1996.tb01082.x     Document Type: Article

References (48)

1. Engelhard, V.H. (1994) Sei. Am. August, 44-51
2. Unanue, E.R. (1992) Curr. Opin. Immunol. 4, 63-69
3. Rötzschke, O. & Falk, K. (1994) Curr. Opin. Immunol. 6,45-51
4. Harding, C.V., Roof, R.W., Alien, P.M. & Unanue, E.R. (1991) Proc. Nail. Acad. Sei. USA 88, 2740-2744
5. Ishioka, G.Y., Lamont, A.G., Thomson, D., Bulbow, N., Gaeta, F.C.A., Sette, A. & Grey, H.M. (1992) J. Immunol 148, 2446-2451
6. Chicz, R.M., Urban, R.G., Gorga, J.C., Vignali, D.A.A., Lane, W.S. & Strominger J.L. (1993) J. Exp. Mcd. 178, 27-47
7. Michaëlsson, E., Malmström, V., Reis, S., Engström, A., Burkhardt, H. & Holmdahl, R. (1994) J. Exp. Med. 180, 745-749
8. Harding, C.V., Kihlberg, J., Elofsson, M., Magnusson, G. & Unanue, E.R. (1993) J. Immunol. 151, 2419-2425
9. Mouritsen, S., Meldal, M., Christiansen-Brams, I., Elsner, H. & Werdelin, O. (1994) Eitr. J. Immunol. 24, 1066-1072
10. Haurum, J.S., Arsequell, G., Lellouch, A.C., Wong, S.Y.C., Dwek, R.A., McMichael, A.J. & Elliot, T. (1994) / Exp. A fed. 180, 739-744
11. Nudelman, E., Kannagi, R., Hakomori, S., Parsons, M., Lipinski, M., Wiels, J., Fellows, M. & Tursz, T. (1983) Science 220,509-511
12. Elofsson, M., Roy, S., Waise, B. & Kihlberg, J. (1993) Carbohydr. Res. 246, 89-103
13. Allen, P.M., Matsueda, G.R., Evans, R.J., Dunbar, Jr, J.B., Marshall, G.R. & Unanue, E.R. (1987) Nature (London) 327, 713-715
14. Kunz, H. (1987) Angew. Client., Int. Ed. Engl. 26, 294-308
15. Garg, H.G., von dem Bruch, K. & Kunz, H. (1994) in Advances in Carbohydrate Chemistry and Biochemistry (Horion, D. ed.) vol.50, pp.277-310, Academic Press, Inc., San Diego, CA
16. Meldal, M. (1994) in Neoglycoconjugates: Preparation and Applications (Lee, Y.C. & Lee, R.T., eds.), pp 145-198, Academic Press, Inc., San Diego, CA
17. Kunz, H., Waldmann, H. & März, J. (1989) Liebigs Ann. Chem. 45-49
18. Unverzagt, C. & Kunz, H. (1994) BioMed. Client. 2,1189-1201
19. Kihlberg, J. & Vuljanic, T. (1993) Tetrahedron Lett. 34, 6135-6138
20. Meldal, M., Bielfeldt, T., Peters, S., Jensen, K.J., Paulsen, H. & Bock K. (1994) Int. J. Peptide Protein Res. 43, 529-536
21. Sjölin, P., Elofsson, M. & Kihlberg, J. (1996), J. Org. Client. 61, 560-565.
22. Salvador, L.A., Elofsson, M. & Kihlberg, J. (1995) Tetrahedron 51, 5643-5656
23. Polt, R-, Szabô L., Treiberg, J., Li, Y. & Hruby, V.J. (1992) J. Am. Clicm. Soc. 114, 10249-10258
24. Jansson, K., Ahlfors, S., Frejd, T., Kihlberg, J., Magnusson, G., Dahrnen, J., Noori, G. & Stenvall, K. (1988) J Org. Chem. 53, 5629-5647
25. Kisfaludy, L. & Schön, I. (1983) Synthesis 325-327
26. Schmidt, R.R. & Michel, J. (1980) Angew. Chem., Int. Eil. Engl. 19, 731-732
27. Veeneman, G.H., van Leeuwen, S.H. & van Boom, J.H. (1990) Tetrahedron Lett. 31, 1331-1334
28. Konradsson, P., Udodong, U.E. & Fraser-Reid, B. (1990) Tetrahedron Lett. 31, 4313-4316
29. Dasgupta, F. & Garegg, P.J. (1988) Carbohydr. Res. 177, c13-c17
30. Fukase, K., Hasuoka, A., Kinoshita, I., Aoki, Y. & Kusumoto, S. (1995) Tetrahedron 51, 4923-4932
31. Elofsson, M., Broddefalk, J., Ekberg, T. & Kihlberg, J. (1994) Carbohydr. Res. 258, 123-133
32. Wolfrom, M.L. & Thompson, A. (1963) Methods Carbohydr. Chem. 2,211-215
33. Garegg, P.J. & Norberg, T. (1979) Ada Chem. Scand., Ser. B 33, 116-118
34. Rink, H. (1987) Tetrahedron Lett. 28, 3787-3790.
35. Bernatowicz, M.S., Daniels, S.B. & Köster, H. (1989) Tetrahedron Lett. 30, 4645-4648
36. Cameron, L.R., Holder, J.L., Meldal, M. & Sheppard, R.C. (1988) J. Chem. Soc., Perkin Trans, l 2895-2901
37. König, W. & Geiger, R. (1970) Chem. Ber. 103, 788-798
38. Flegel, M. & Sheppard, R.C. (1990) J. Chem. Soc.. Chem. Commun. 536-538
39. King, D.S., Fields, CG. & Fields, G.B. (1990) Int. J. Pcpliik Protein Res. 36, 255-266
40. Paulsen, H., Schultz, M., Klamann, J.-D., Waller, B. & Paal, M. (1985) Liebigs Ann. Client. 2028-2048
41. Dyson, J.H. & Wright, P.E. (1991) Anmt. Rev. Biophys. Biopliys. Chem. 20, 519-538
42. Kihlberg, J., Åhman, J., Walse, B., Drakenberg, T., Nilsson, A., Soderberg-Ahlm, C., Bengtsson, B. & Olsson, H. (1995) J. A fed. Client. 38, 161-169
43. Andreotti, A.H. & Kahne, D. (1993) J. Am. Client. Soc. 115, 3352-3353
44. Jaou, H.C., Scragg, I.G. & Dwek, R.A. (1992) FEBS 307, 343-346
45. Deck, B., Elofsson, M., Kihlberg, J. & Unanue, E.R. (1995) J. Immwtol. 155, 1074-1078
46. Aue, W.P., Bartholdi, E. & Ernst, R.R. (1976) J. Client. Phys. 64, 2229-2246
47. Braunschweiler, L. & Ernst, R.R. (1983) J. Afagn. Reson. 53, 521-528
48. Bax, A. & Davis, D.G. (1985) J. Magn. Reson. 63, 207-213