Reactivity-based one-pot total synthesis of fucose GM1 oligosaccharide: A sialylated antigenic epitope of small-cell lung cancer

Proceedings of the National Academy of Sciences of the United States of America

Volumn 100, Issue 3, 2003, Pages 797-802

  Mong, Tony Kwok Kong ^a   Lee, Hing Ken ^a   Durón, Sergio G ^a   Wong, Chi Huey ^a  

^a SCRIPPS RESEARCH INSTITUTE   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

1 (BENZENESULFINYL)PIPERIDINE; EPITOPE; GANGLIOSIDE GM1; OLIGOSACCHARIDE; PIPERIDINE DERIVATIVE; SIALIC ACID; SUCCINIMIDE DERIVATIVE; THIOGLYCOSIDE; TRIFLUOROMETHANESULFONIC ACID; UNCLASSIFIED DRUG;

ANIMAL TISSUE; ANTIGENICITY; ARTICLE; CARBOHYDRATE ANALYSIS; CARBOHYDRATE SYNTHESIS; CHEMICAL REACTION; DATA BASE; LUNG SMALL CELL CANCER; NONHUMAN; PRIORITY JOURNAL; REACTION ANALYSIS; REACTION TIME; SIALYLATION;

CARBOHYDRATE SEQUENCE; CARCINOMA, SMALL CELL; DISACCHARIDES; EPITOPES; FUCOSE; LUNG NEOPLASMS; MOLECULAR SEQUENCE DATA; N-ACETYLNEURAMINIC ACID; OLIGOSACCHARIDES;

ANIMALIA;

EID: 0037417868     PISSN: 00278424     EISSN: None     Source Type: Journal    
DOI: 10.1073/pnas.0337590100     Document Type: Article

References (25)

1. Macher, B. A., Pacuzska, T., Mullin, B. R., Sweeley, C. C., Brady, R. O. & Fishman, P. H. (1979) Biochim. Biophys. Acta 588, 35-43.
2. Dickler, M. N., Ragupathi, G., Liu, N. X., Musselli, C., Martino, D. J., Miller, V. A., Kris, M. G., Brezicka, F.-T., Livingston, P.-O. & Grant, S. C. (1999) Clin. Cancer Res. 5, 2773-2779.
3. Nilsson, O., Mansson, J.-E., Brezicka, F.-T., Holmgren, J., Lindholm, L., Sorenson, S., Yngvason, F. & Svennerholm, L. (1984) Glycoconjugate J. 1, 43-49.
4. Brezicka, F.-T., Olling, S., Nilsson, O., Bergh, J., Holmgren, J., Sorenson, S., Yngvason, F. & Lindholm, L. (1989) Cancer Res. 49, 1300-1305.
5. Pongdee, R., Wu, B. & Sulikowski, G. A. (2001) Org. Lett. 3, 3523-3525.
6. Fridman, M., Solomon, D., Yogev, S. & Baasov, T. (2002) Org. Lett. 4, 281-283.
7. Hewitt, M. C., Snyder, D. A. & Seeberger, P. H. (2002) J. Am. Chem. Soc. 124, 13434-13436.
8. Zhang, Z., Ollmann, I. R., Ye, X.-S., Wischnat, R., Baasov, T. & Wong, C.-H. (1999) J. Am. Chem. Soc. 121, 734-753.
9. Allen, J. R. & Danishefsky, S. J. (1999) J. Am. Chem. Soc. 121, 10875-10882.
10. Kwon, O. & Danishesky, S. J. (1998) J. Am. Chem. Soc. 120, 1588-1599.
11. De Pouilly, P., Chénedé, A., Mallet, J.-M. & Sinäy, P. (1993) Bull. Soc. Chim. Fr. 130, 256-262.
12. Sim, M. M., Kondo, H. & Wong, C. H. (1993) J. Am. Chem. Soc. 115, 2260-2267.
13. Koeller, K. M. & Wong, C. H. (2000) Chem. Rev. 100, 4465-4493.
14. Burkhart, F., Zhang, Z., Wacowich-Sgarbi, S. & Wong, C.-H. (2001) Angew. Chem. Int. Ed. 40, 1274-1277.
15. Mong, T. K.-K. & Wong, C.-H. (2002) Angew. Chem. Int. Ed. 41, 4087-4090.
16. Mong, T. K.-K., Huang, C.-Y. & Wong, C.-H. (2002) J. Org. Chem., in press.
17. Ye, X.-S. & Wong, C.-H. (2001) J. Org. Chem. 65, 2410-2431.
18. Crich, D. & Smith, M. (2001) J. Am. Chem. Soc. 123, 9015-9020.
19. Furniss, B. S., Hannaford, A. J., Smith, P. W. G. & Tatchen, A. R. (1989) in Vogel's Textbook of Practical Organic Chemistry, ed. Vogel, A. I. (Wiley, New York), pp. 650-651.
20. van Boom, J. H. & Burgers, P. M. J. (1976) Tetrahedron Lett. 4875-4877.
21. Schmidt, R. R., Behrendt, M. & Toepfer, A. (1990) Synletters, 694-696.
22. Veenenman, G. H. & van Boom, J. H. (1990) Tetrahedron Lett. 31, 275-278.
23. Fugedi, P. & Garegg, P. J. (1986) Carbohydr. Res. 149, C9-C12.
24. McCloskey, C. M. (1957) Adv. Carbohydr. Res. 12, 137-156.
25. Yagi, H., Thakker, D. R., Lehr, R. E. & Jerina, D. M. (1979) J. Org. Chem. 44, 3442-3444.