Synthesis of branched oxime-linked peptide mimetics of the MUC1 containing a universal T-helper epitope

Chemistry - A European Journal

Volumn 10, Issue 24, 2004, Pages 6353-6360

  Cremer, Gaëlle Anne ^a   Bureaud, Nicole ^a   Lelièvre, Dominique ^a   Piller, Véronique ^a   Piller, Friedrich ^a   Delmas, Agnès ^a  

^a CENTRE DE BIOPHYSIQUE MOLÉCULAIRE   (France)

Author keywords

Antibodies; Chemoselective ligation; Oxime; Peptides

Indexed keywords

ANTIBODIES; ANTIGENS; DRUG THERAPY; IMMUNOLOGY; SYNTHESIS (CHEMICAL); TUMORS;

IMMUNOGENIC; MASKED ALDEHYDES; PEPTIDE MIMETICS; TOLERANCE BARRIER;

POLYPEPTIDES;

ALDEHYDE; ANTIBODY; ANTIGEN; EPITOPE; MUCIN 1; OXIME; PEPTIDE;

ACCURACY; ANIMAL EXPERIMENT; ARTICLE; CHEMICAL BOND; CHEMISTRY; CONTROLLED STUDY; DEPROTECTION REACTION; DRUG SCREENING; DRUG SYNTHESIS; IMMUNE RESPONSE; IMMUNOGENICITY; IMMUNOLOGICAL TOLERANCE; IMMUNOTHERAPY; MOLECULAR RECOGNITION; MOUSE; NONHUMAN; PEPTIDE SYNTHESIS; TUMOR;

AMINO ACID SEQUENCE; CA-15-3 ANTIGEN; EPITOPES; HUMANS; MOLECULAR SEQUENCE DATA; OXIMES; PEPTIDES; T-LYMPHOCYTES, HELPER-INDUCER;

EID: 10944228789     PISSN: 09476539     EISSN: None     Source Type: Journal    
DOI: 10.1002/chem.200400780     Document Type: Article

References (45)

1. F. G. Hanisch, S. Muller, Glycobiology 2000, 10, 439-449.
2. M. J. Ligtenberg, H. L. Vos, A. M. Gennissen, J. Hilkens, J. Biol. Chem. 1990, 265, 5573-5578.
3. A. Girling, J. Bartkova, J. Burchell, S. Gendler, C. Gillett, J. Taylor-Papdimitriou, Int. J. Cancer 1989, 43, 1972-1976.
4. K. N. Syrigos, A. J. Karayiannakis, A. Zbar, Anticancer Res. 1999, 19, 5239-5244.
5. A. N. Houghton, K. O. Lloyd, Nat. Med. 1998, 4, 270-271.
6. E. Krambovitis, G. Hatzidakis, K. Barlos, J. Biol. Chem. 1998, 273, 10874-10879.
7. S. Zhang, L. A. Graeber, F. Helling, G. Ragupathi, S. Adluri, K. O. Lloyd, P. O. Livingston, Cancer Res. 1996, 56, 3315-3319.
8. H. M. Etlinger, Immunol. Today 1992, 92, 52-55.
9. a) S. Keil, C. Claus, W. Dippold, H. Kunz, Angew. Chem. 2001, 113, 379-382; S. Keil, C. Claus, W. Dippold, H. Kunz, Angew. Chem. 2001, 113, 379-382; Angew. Chem. Int. Ed. 2001, 40, 366-369;
10. a) S. Keil, C. Claus, W. Dippold, H. Kunz, Angew. Chem. 2001, 113, 379-382; S. Keil, C. Claus, W. Dippold, H. Kunz, Angew. Chem. 2001, 113, 379-382; Angew. Chem. Int. Ed. 2001, 40, 366-369;
11. a) S. Keil, C. Claus, W. Dippold, H. Kunz, Angew. Chem. 2001, 113, 379-382; S. Keil, C. Claus, W. Dippold, H. Kunz, Angew. Chem. 2001, 113, 379-382; Angew. Chem. Int. Ed. 2001, 40, 366-369;
12. b) M. D. Lairmore, A. M. DiGeorge, S. F. Conrad, A. V. Trevino, R. B. Lal, P. T. Kaumaya, J. Virol. 1995, 69, 6077-6089.
13. P. Panina-Bordignon, A. Tan, A. Termijtelen, S. Demotz, G. Corradin, A. Lanzavecchia, Eur. J. Immunol. 1989, 20, 2237-2242.
14. J. Alexander, J. Sidney, S. South-wood, J. Ruppert, C. Oseroff, A. Maewal, K. Snoke, H. M. Serra, R. T. Kubo, A. Sette, H. M. Grey, Immunity, 1994, 1, 751-761.
15. K. Rose, J. Am. Chem. Soc. 1994, 116, 30-33.
16. a) L. E. Canne, A. R. Ferré d'Amaré, S. K. Burley, S. B. H. Kent, J. Am. Chem. Soc. 1995, 117, 2998-3007;
17. b) G. G. Kochendoerfer, J. M. Tack, S. Cressman, Bioconjugate Chem. 2002, 13, 474-480;
18. c) G. Thumshirn, U. Hersel, S. L. Goodman, H. Kessler, Chem. Eur. J. 2003, 9, 2717-2725.
19. a) J. Shao, J. P. Tam, J. Am. Chem. Soc. 1995, 117, 3893-3899;
20. b) K. Rose, W. Zeng, P. O. Regamey, I. V. Chernushevich, K. G. Standing, H. F. Gaertner, Bioconjugate Chem. 1996, 7, 552-556.
21. E. H. Nardin, J. M. Calvo-Calle, G. A. Oliveira, R. S. Nussenzweig, M. Schneider, J. M. Tiercy, L. Loutan, D. Hochstrasser, K. Rose, J. Immunol. 2001, 166, 481-489.
22. a) S. E. Cervigni, P. Dumy, M. Mutter, Angew. Chem. 1996, 108, 1325-1328; Angew. Chem. Int. Ed. Engl. 1996, 35, 1230-1232;
23. a) S. E. Cervigni, P. Dumy, M. Mutter, Angew. Chem. 1996, 108, 1325-1328; Angew. Chem. Int. Ed. Engl. 1996, 35, 1230-1232;
24. b) D. Boturyn, J. L. Coll, E. Garanger, M. C. Favrot, P. Dumy, J. Am. Chem. Soc. 2004, 126, 5730-5739.
25. D. Lelièvre, C. Buré, F. Laot, A. Delmas, Tetrahedron Lett. 2001, 42, 235-238.
26. H. Rink, Tetrahedron Lett. 1987, 28, 3787-3790.
27. S. S. Wang, J. Am. Chem. Soc. 1973, 95, 1328-1333.
28. C. Buré, D. Lelièvre, A. Delmas, Rapid Commun. Mass Spectrom. 2000, 14, 2158-2164.
29. K. F. Geoghegan, J. G. Stroh, Bioconjugate Chem. 1992, 3, 138-146.
30. a) D. Lelièvre, H. Chabane, A. Delmas, Tetrahedron Lett. 1998, 39, 9675-9678;
31. b) D. Lelièvre, O. Turpin, S. El Kazzouli, A. Delmas, Tetrahedron 2002, 58, 5525-5533.
32. E. Kaiser, R. L. Colescott, C. D. Bossinger, P. I. Cook, Anal. Biochem. 1970, 34, 595-598.
33. P. Alewood, D. Alewood, L. Miranda, S. Love, W. Meutermans, D. Wilson, Methods Enzymol. 1997, 289, 14-29.
34. A. R. Mitchell, B. W. Erickson, M. N. Ryabstev, R. S. Hodges, R. B. Merrifield, J. Am. Chem. Soc. 1976, 98, 7357-7362.
35. M. Schnolzer, P. Alewood, A. Jones, D. Alewood, S. B. Kent, Int. J. Pept. Protein Res. 1992, 40, 180-193.
36. J. Farrera-Sinfreu, M. Royo, F. Albericio, Tetrahedron Lett. 2002, 43, 7813-7815.
37. D. Kadereit, P. Deck, I. Heinemann, H. Waldmann, Chem. Eur. J. 2001, 7, 1184-1193.
38. E. Atherton, V. Woolley, R. C. Sheppard, J. Chem. Soc. Chem. Commun. 1980, 970-971.
39. J. C. Spetzler, T. Hoeg-Jensen, Tetrahedron Lett. 2002, 43, 2303-2306, and references therein.
40. a) C. H. Depuy, B. W. Ponder, J. Am. Chem. Soc. 1959, 81, 4629-4631;
41. b) E. B. Hershbeg, J. Org. Chem. 1948, 13, 542-548.
42. R. E. Offord, H. F. Gaertner, T. N. Wells, A. E. Proudfoot, Methods Enzymol. 1997, 287, 348-369.
43. C. Buré, W. Gobert, D. Lelièvre, A. Delmas, J. Mass Spectrom. 2001, 36, 1149-1155.
44. L. A. Carpino, J. Am. Chem. Soc. 1993, 115, 4397-4398.
45. E. Harlow, D. Lane, Antibodies: A laboratory manual, Cold Spring Laboratory Press, Cold Spring Harbor, NY, 1988.