Probing cell surface 'glyco-architecture' through total synthesis. Immunological consequences of a human blood group determinant in a clustered mucin-like context [6]

Journal of the American Chemical Society

Volumn 121, Issue 45, 1999, Pages 10636-10637

  Glunz, Peter W ^a   Hintermann, Samuel ^a   Schwarz, Jacob B ^a   Kuduk, Scott D ^a   Chen, Xiao Tao ^b   Williams, Lawrence J ^a   Sames, Dalibor ^a   Danishefsky, Samuel J ^a,b   Kudryashov, Valery ^a   Lloyd, Kenneth O ^a  

^a MEMORIAL SLOAN KETTERING CANCER CENTER   (United States)

^b Columbia University ^*  (United States)

Author keywords

[No Author keywords available]

Indexed keywords

GLYCOPEPTIDE; MUCIN;

ACETYLATION; BLOOD GROUP; CYTOARCHITECTURE; HUMAN; IMMUNOGENICITY; LETTER; PEPTIDE ANALYSIS; PEPTIDE SYNTHESIS; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 13044265836     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja992309s     Document Type: Letter

References (28)

1. Greenwell, P. Glycoconjugate J. 1997, 14, 159-173.
2. Müller, S.; Goletz, S.; Packer, N.; Gooley, A.; Lawson, A. M.; Hanisch, F. G. J. Biol. Chem. 1997, 272, 24780-24793.
3. Lloyd, K. O. Am. J. Clin. Pathol. 1987, 87, 129-139.
4. Yin, B. W. T.; Finstad, C. L.; Kitamura, K.; Federici, M. J.; Welshinger, M.; Kudryashov, V.; Hoskins, W. J.; Welt, S.; Lloyd, K. O. Int. J. Cancer 1996, 65, 406-412.
5. (a) Bessler, W. G.; Cox, M.; Lex, A.; Suhr, B.; Wiesmuller, K. H.; Jung, G. J. Immunol. 1985, 135, 1900-1905.
6. (b) Toyokuni, T.; Hakomori, S.-I.; Singhal, A. K. Bioorg. Med. Chem. 1994, 2, 1119-1132
7. (a) Dmitriev, B. A.; Ovchinnikov, M. V.; Lapina, E. B.; Pluzhnikova, G. N.; Lopyrev, I. V.; Chernyak, A. Y. Glycoconjugate J. 1992, 9, 168-173.
8. (b) Reichel, F.; Ashton, P. R.; Boons, G.-J. Chem. Commun. 1997, 2087-2088.
9. (c) Reichel, F.; Roelofsen, A. M.; Geurts, H. P. M.; Hämäläinen, T. I.; Feiters, M. C.; Boons, G.-J. J. Am. Chem. Soc., 1999, 121, 7989-7997.
10. Danishefsky, S. J.; Bilodeau, M. T. Angew. Chem., Int. Ed. Engl. 1996, 35, 1380-1419.
11. (a) Kuduk, S. D.; Schwarz, J. B.; Chen, X.-T.; Glunz, P. W.; Sames, D.; Ragupathi, G.; Livingston, P. O.; Danishefsky, S. J. J. Am. Chem. Soc. 1998, 120, 12474-12485.
12. (b) Schwarz, J. B.; Kuduk, S. D.; Chen, X.-T.; Sames, D.; Glunz, P. W.; Danishefsky, S. J. J. Am. Chem. Soc. 1999, 121, 2662-2673.
13. For earlier demonstrations of the cassette concept, albeit in simpler settings, see: (a) Paulsen, H.; Hoick, J.-P. Carbohydr. Res. 1982, 109, 89-107. (b) Liebe, B. and Kunz, H. Tetrahedron Lett. 1994, 35, 8777-8778. (c) Liebe, B.; Kunz, H. Helv. Chim. Acta 1997 80, 1473-1482. (d) Meinjohanns, E.; Meldal, M.; Schleyer, A.; Paulsen, H.; Bock, K. J. Chem. Soc., Perkin Trans. 1 1996, 985-993. (e) Qiu, D. and Koganty, R. R. Tetrahedron Lett. 1997, 38, 45-48. (f) Qiu, D.; Koganty, R. R. Tetrahedron Lett. 1997, 38, 961-964. (g) Nakahara, Y.; Nakahara, Y.; Ito, Y.; Ogawa, T. Tetrahedron Lett. 1997, 38, 7211-7214.
14. For earlier demonstrations of the cassette concept, albeit in simpler settings, see: (a) Paulsen, H.; Hoick, J.-P. Carbohydr. Res. 1982, 109, 89-107. (b) Liebe, B. and Kunz, H. Tetrahedron Lett. 1994, 35, 8777-8778. (c) Liebe, B.; Kunz, H. Helv. Chim. Acta 1997 80, 1473-1482. (d) Meinjohanns, E.; Meldal, M.; Schleyer, A.; Paulsen, H.; Bock, K. J. Chem. Soc., Perkin Trans. 1 1996, 985-993. (e) Qiu, D. and Koganty, R. R. Tetrahedron Lett. 1997, 38, 45-48. (f) Qiu, D.; Koganty, R. R. Tetrahedron Lett. 1997, 38, 961-964. (g) Nakahara, Y.; Nakahara, Y.; Ito, Y.; Ogawa, T. Tetrahedron Lett. 1997, 38, 7211-7214.
15. For earlier demonstrations of the cassette concept, albeit in simpler settings, see: (a) Paulsen, H.; Hoick, J.-P. Carbohydr. Res. 1982, 109, 89-107. (b) Liebe, B. and Kunz, H. Tetrahedron Lett. 1994, 35, 8777-8778. (c) Liebe, B.; Kunz, H. Helv. Chim. Acta 1997 80, 1473-1482. (d) Meinjohanns, E.; Meldal, M.; Schleyer, A.; Paulsen, H.; Bock, K. J. Chem. Soc., Perkin Trans. 1 1996, 985-993. (e) Qiu, D. and Koganty, R. R. Tetrahedron Lett. 1997, 38, 45-48. (f) Qiu, D.; Koganty, R. R. Tetrahedron Lett. 1997, 38, 961-964. (g) Nakahara, Y.; Nakahara, Y.; Ito, Y.; Ogawa, T. Tetrahedron Lett. 1997, 38, 7211-7214.
16. For earlier demonstrations of the cassette concept, albeit in simpler settings, see: (a) Paulsen, H.; Hoick, J.-P. Carbohydr. Res. 1982, 109, 89-107. (b) Liebe, B. and Kunz, H. Tetrahedron Lett. 1994, 35, 8777-8778. (c) Liebe, B.; Kunz, H. Helv. Chim. Acta 1997 80, 1473-1482. (d) Meinjohanns, E.; Meldal, M.; Schleyer, A.; Paulsen, H.; Bock, K. J. Chem. Soc., Perkin Trans. 1 1996, 985-993. (e) Qiu, D. and Koganty, R. R. Tetrahedron Lett. 1997, 38, 45-48. (f) Qiu, D.; Koganty, R. R. Tetrahedron Lett. 1997, 38, 961-964. (g) Nakahara, Y.; Nakahara, Y.; Ito, Y.; Ogawa, T. Tetrahedron Lett. 1997, 38, 7211-7214.
17. For earlier demonstrations of the cassette concept, albeit in simpler settings, see: (a) Paulsen, H.; Hoick, J.-P. Carbohydr. Res. 1982, 109, 89-107. (b) Liebe, B. and Kunz, H. Tetrahedron Lett. 1994, 35, 8777-8778. (c) Liebe, B.; Kunz, H. Helv. Chim. Acta 1997 80, 1473-1482. (d) Meinjohanns, E.; Meldal, M.; Schleyer, A.; Paulsen, H.; Bock, K. J. Chem. Soc., Perkin Trans. 1 1996, 985-993. (e) Qiu, D. and Koganty, R. R. Tetrahedron Lett. 1997, 38, 45-48. (f) Qiu, D.; Koganty, R. R. Tetrahedron Lett. 1997, 38, 961-964. (g) Nakahara, Y.; Nakahara, Y.; Ito, Y.; Ogawa, T. Tetrahedron Lett. 1997, 38, 7211-7214.
18. For earlier demonstrations of the cassette concept, albeit in simpler settings, see: (a) Paulsen, H.; Hoick, J.-P. Carbohydr. Res. 1982, 109, 89-107. (b) Liebe, B. and Kunz, H. Tetrahedron Lett. 1994, 35, 8777-8778. (c) Liebe, B.; Kunz, H. Helv. Chim. Acta 1997 80, 1473-1482. (d) Meinjohanns, E.; Meldal, M.; Schleyer, A.; Paulsen, H.; Bock, K. J. Chem. Soc., Perkin Trans. 1 1996, 985-993. (e) Qiu, D. and Koganty, R. R. Tetrahedron Lett. 1997, 38, 45-48. (f) Qiu, D.; Koganty, R. R. Tetrahedron Lett. 1997, 38, 961-964. (g) Nakahara, Y.; Nakahara, Y.; Ito, Y.; Ogawa, T. Tetrahedron Lett. 1997, 38, 7211-7214.
19. For earlier demonstrations of the cassette concept, albeit in simpler settings, see: (a) Paulsen, H.; Hoick, J.-P. Carbohydr. Res. 1982, 109, 89-107. (b) Liebe, B. and Kunz, H. Tetrahedron Lett. 1994, 35, 8777-8778. (c) Liebe, B.; Kunz, H. Helv. Chim. Acta 1997 80, 1473-1482. (d) Meinjohanns, E.; Meldal, M.; Schleyer, A.; Paulsen, H.; Bock, K. J. Chem. Soc., Perkin Trans. 1 1996, 985-993. (e) Qiu, D. and Koganty, R. R. Tetrahedron Lett. 1997, 38, 45-48. (f) Qiu, D.; Koganty, R. R. Tetrahedron Lett. 1997, 38, 961-964. (g) Nakahara, Y.; Nakahara, Y.; Ito, Y.; Ogawa, T. Tetrahedron Lett. 1997, 38, 7211-7214.
20. Danishefsy, S. J.; Behar, V.; Randolph, J. T.; Lloyd, K. O. J. Am. Chem. Soc. 1995, 117, 5701-5711.
21. (a) Gordon, D. and Danishefsky, S. J. Carbohydr. Res. 1990, 206, 361.
22. (b) Seeberger, P. H.; Eckhardt, M.; Gutteridge, C. E.; Danishefsky, S. J. J. Am. Chem. Soc. 1997, 119, 10064-10072.
23. (a) Veeneman, G. H.; van Leeuwen, S. H.; van Boom, J. H. Tetrahedron Lett. 1990, 31, 1331-1334.
24. (b) Konradsson, P.; Udodong, U. E.; Fraser-Reid, B. Tetrahedron Lett. 1990, 31, 4313-4316.
25. Mootoo, D. R.; Date, V.; Fraser-Reid, B. J. Am. Chem. Soc. 1988, 110, 2662.
26. Carpino, L. A. J. Am. Chem. Soc. 1993, 115, 4397-4398.
27. Kudryashov, V.; Kim, H. M.; Ragupathi, G.; Danishefsky, S. J.; Livingston. P. O.; Lloyd, K. O. Cancer Immunol. Immunother. 1998, 45, 281-286.
28. Kitamura, K.; Stockert, E.; Garin-Chesa, P.; Welt, S.; Lloyd, K. O.; Armour, K. L.; Wallace, T. P.; Harris, W. J.; Carr, F. J.; Old, L. J. Proc. Natl. Acad. Sci. (Wash.) 1994, 91, 12957-12961.