Convergent total synthesis of a tumour-associated mucin motif

Nature

Volumn 389, Issue 6651, 1997, Pages 587-591

  Sames, Dalibor ^a   Chen, Xiao Tao ^b   Danishefsky, Samuel J ^b  

^a MEMORIAL SLOAN KETTERING CANCER CENTER   (United States)

^b Och Spine at New York Presbyterian Hospitals   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

(2,6) SIALYL T ANTIGEN; MUCIN; TRISACCHARIDE; TUMOR ANTIGEN; UNCLASSIFIED DRUG;

ARTICLE; PRIORITY JOURNAL; PROTEIN ASSEMBLY; PROTEIN DOMAIN; PROTEIN SYNTHESIS;

CARBOHYDRATE SEQUENCE; MOLECULAR SEQUENCE DATA; MUCINS;

MURINAE;

EID: 0030773830     PISSN: 00280836     EISSN: None     Source Type: Journal    
DOI: 10.1038/39292     Document Type: Article

References (31)

1. Ragupathi, G. et al. Immunization of mice with a fully synthetic globo-H antigen results in antibodies against human cancer cells: A combined chemical-immunological approach to the fashioning of an anticancer vaccine Angew. Chem. Int. Edn Engl. 36, 125-128 (1997).
2. Toyokuni, T. & Singhal, A. K. Synthetic carbohydrate vaccines based on tumor-associated antigens. Chem. Soc. Rev. 24, 231-242 (1995).
3. Bilodeau, M. T. & Danishefsky, S. J. Glycals in organic synthesis: the evolution of compreshensive strategies for the assembly of oligosaccharides and glycoconjugates of biological consequence. Angew. Chem. Int. Edn Engl. 35, 1381-1419 (1996).
4. Deck, B., Elofsson, K., Kihlberg, J. & Unanue, E. E. Specificity of glycopeptide-specific T cells. J. Immunol. 155, 1074-1078 (1995).
5. Haurum, J. S. et al. Recognition of carbohydrate by major histocompatibility complex class I-restricted, glycopeptide-specific cytotoxic T lymphocytes. J. Exp. Med. 180, 739-744 (1994).
6. Mouritsen, S. et al. Attachment of oligosaccharides to peptide antigen profoundly affects binding to major histocompatibility complex class II molecules and peptide immunogenicity. Eur. J. Immunol. 24, 1066-1072 (1994).
7. Sieling, P. A. et al. CD1-restricted T cell recognition of microbial lipoglycan antigens. Science 269, 227-230 (1995).
8. Jenson, T. et al. Carbohydrate and peptide specificity of MHC Class II-restricted T cell hybridomas raised against an O-glycosylated self peptide. J. Immunol. 3769-3778 (1997).
9. Bill, R. M. & Flitsch, S. L. Chemical and biological approaches to glycoprotein synthesis. Chem. Biol. 3, 145-149 (1996).
10. Witte, K., Sears, P., Martin, K. & Wong, C.-H. Enzymatic glycoprotein synthesis: preparation of ribonuclease glycoforms via enzymatic glycopeptide condensation and glycosylation. J. Am. Chem. Soc. 119, 2114-2118 (1997).
11. Tsuda, T. & Nithimura, S.-I. Synthesis of an antifreeze glycoprotein analogue: efficient preparation of sequential glycopeptide polymers. J. Chem. Soc. Chem. Commun. 2779-2780 (1996).
12. Nakahara, Y., Iijima, H. & Ogawa, T. in Synthetic Oligosaccharides, Indispensable Probes for the Life Sciences (ed. P. Kovác) 249-266 (ACS Symp. Ser. 560, ACS, Washington DC, 1994).
13. Jenkins, N., Parekh, R.B. & James, D. C. Getting the glycosylation right: Implications for the biotechnology industry. Nature Biotechnol. 14, 975-981 (1996).
14. Carlstedt, I. & Davies, J. R. Glycoconjugates facing the outside world. Biochem Soc. Trans. 25, 214-219 (1997).
15. Finn, O. J. et al. MUC-1 epithelial tumor mucin-based immunity and cancer vaccines. Immunol. Rev. 145, 61-89 (1995).
16. Fukuda, M., Carlsson, S.R., Klock, J. C. & Dell, A. Structures of O-linked oligosaccharides isolated from normal granulocytes, chronic myelogenous leukemia cells, and acute myelogenous leukemia cells. J. Biol. Chem. 261, 12796-12806 (1986).
17. Saitoh, O., Gallagher, R.E. & Fukuda, M. Expression of aberrant O-glycans attached to leukosialin in differentiation-deficient HL-60 cells. Cancer Res. 51, 2854-2862 (1991).
18. Pallant, A. et al. Characterization of cDNAs encoding human leukosialin and localization of the leukosialin gene to chromosome 16. Proc. Natl Acad. Sci. USA 86, 1328-1332 (1989).
19. Kunz, H. & Schultz, M. in Glycopeptides and Related Compounds (eds Large, D. G. & Warren, Ch. D.) 23 (Dekker, New York, 1997).
20. Paulsen, H. et al. New solid phase oligosaccharide synthesis on glycopeptides bound to a solid phase. J. Chem. Soc. Perkin Trans. 1 281-293 (1997).
21. Liebe, B. & Kunz, H. Solid phase synthesis of a tumor-associated sialyl-Tn antigen glycopeptide with a partial sequence of the "tandem repeat" of the Muc-1 mucin. Angew. Chem. Int. Edn Engl. 36, 618-621 (1997).
22. Qui, D. & Koganty, R. R. Mucin type glycopeptides: synthesis of core 2, core 6 and F1-α building blocks and some unexpected reactions. Tetrahedr. Lett. 38, 45-48 (1997).
23. Elofsson, M., Salvador, L.A. & Kihlberg, J. Preparation of Tn and sialyl Tn building blocks used in Fmoc solid-phase synthesis of glycopeptide fragments from HIV gp120. Tetrahedron 53, 369-390 (1997).
24. Szabo, L., Ramza, J., Langdon, C. & Polt, R. Stereoselective synthesis of O-serinyl/threonyl-2-acetamido-2-deoxy-α or β-glycosides. Carbohydr. Res. 274, 11-28 (1995).
25. 3. Glycoconjugate J. 10, 16-25 (1993).
26. Sim, M. M., Kondo, H. & Wong, C.-H. Synthesis and use of glycosyl phosphites: an effective route to glycosyl phosphates, sugar nucleotides and glycosides. J. Am. Chem. Soc. 115, 2260-2267 (1993).
27. Schmidt, R. R. & Kinzy, W. Anomeric oxygen activation for glycoside synthesis. Adv. Carbohydr. Chem. Biochem. 50, 84-123 (1994).
28. Kondo, H. et al. Glycosyl phosphites as glycosylation reagents: Scope and mechanism. J. Org. Chem. 59, 864-867 (1994).
29. Paulsen, H., Rauwald, W. & Weichert, U. Glycosidierung mit thioglycosiden von oligosacchariden zu segmenten von O-glycoproteinen. Liebigs Ann. Chem. 75-86 (1988).
30. Iijima, H. & Ogawa, T. Synthesis of a mucin type O-glycosylated amino acid, β-Gal(1 → 3)-[α-Neu5Ac-(2 → 6)]-α-GalNac-(1 → 3)-Ser. Carbohydr. Res. 186, 95-106 (1989).
31. Jiang, J., Li, W.-R. & Joullié, M. Selective removal of fluorenylmethoxycarbonyl (Fmoc) groups under mild conditions. Synth. Commun. 24, 187-195 (1994).