Reactivity-based one-pot synthesis of a Lewis Y carbohydrate hapten: A colon-rectal cancer antigen determinant

Angewandte Chemie - International Edition

Volumn 41, Issue 21, 2002, Pages 4087-4090

  Mong, Kwok Kong T ^a   Wong, Chi Huey ^a  

^a SCRIPPS RESEARCH INSTITUTE   (United States)

Author keywords

Antigens; Antitumor agents; Glycosylation; Oligosaccharides; Reactivity based synthesis

Indexed keywords

ANTIGENS; STEREOCHEMISTRY; SYNTHESIS (CHEMICAL); TUMORS;

BUILDING UNITS;

CARBOHYDRATES;

BLOOD GROUP ANTIGEN; CARBOHYDRATE; CARBOHYDRATE DERIVATIVE; EPITOPE; HAPTEN; LEWIS Y ANTIGEN; TUMOR ANTIGEN; TUMOR MARKER; UNCLASSIFIED DRUG;

ANTIGEN DETECTION; ANTIGEN STRUCTURE; ARTICLE; BLOOD GROUP LEWIS SYSTEM; CANCER DIAGNOSIS; CARBOHYDRATE ANALYSIS; CHEMICAL ANALYSIS; CHEMICAL REACTION; CHEMISTRY; COLON CANCER; COLORECTAL CANCER; COLORECTAL TUMOR; CONFORMATION; HUMAN; IMMUNOLOGY; MOLECULAR GENETICS; RECTUM CANCER; STEREOSPECIFICITY; SYNTHESIS;

ANTIGENS, NEOPLASM; CARBOHYDRATE CONFORMATION; CARBOHYDRATE SEQUENCE; CARBOHYDRATES; COLORECTAL NEOPLASMS; EPITOPES; HAPTENS; LEWIS BLOOD-GROUP SYSTEM; MOLECULAR SEQUENCE DATA;

EID: 85047698715     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: None     Document Type: Article

References (20)

1. A. Varki, R. Cummings, J. Esko, H. Freeze, G. Hart, J. Marth, Essentials of Glycobiology, CSHL, Cold Spring Harbor, New York, 1999, 211-252.
2. a) p. M. Pour, M. M. Tempero, H. Takasaki, E. Uchida, Y. Takiyama, D. A. Burnett, Z. Steplewski, Cancer Res. 1988, 48, 5422;
3. b) W. Masayuki, S. Tomohiro, S. Toshihito, N. Taiichi, I. Takayuki, I. Masato, S. Yasuko, I. Kyoichi, O. Akiharu, Cancer 1995, 75, 2827;
4. c) E. J. Nichols, R. Kannagi, S.-I. Kakomori, M. J. Krantz, A. Fuks, I. Immunol. 1985, 135, 1911;
5. d) A. Brown, I. O. Ellis, M. J. Embleton, R. W. Baldwin, D. R. Turner, J. D. Hardcastle, Int. J. Cancer 1984, 33, 727.
6. S, J. Danishefsky, J. R. Allen, Angew. Chem. 2000, 112, 882; Angew. Chem. Int. Ed. 2000, 39, 836.
7. S, J. Danishefsky, J. R. Allen, Angew. Chem. 2000, 112, 882; Angew. Chem. Int. Ed. 2000, 39, 836.
8. J. R. Allen, C. R. Harris, S. J. Danishefsky, J. Am. Chem. Soc. 2001, 123, 1890.
9. J.-C. Jacquinet, P. Sinaÿ, J. Org. Chem. 1977, 42, 720.
10. a) R. R. Schmidt, A. Toepfer, Tetrahedron Lett. 1991, 32, 3353;
11. b) R. Windm̈ller, R. R. Schmidt, Tetrahedron Lett. 1994, 35. 7927;
12. c) S. J. Danishesfsky, V. Behar, J. T. Randolph, K. O. Lloyd, J. Am. Chem. Soc. 1995, 117, 5701.
13. Z. Zhang, I. R. Ollmann, X.-S. Ye, R. Wischnat, T. Baasov, C.-H. Wong, J. Am. Chem. Soc. 1999, 121, 734.
14. F. Burkhart, Z. Zhang, S. Wacowich-Sgarbi, C.-H. Wong, Angew. Chem. 2001, 113, 1314; Angew. Chem. Int. Ed. 2001, 40, 1274.
15. F. Burkhart, Z. Zhang, S. Wacowich-Sgarbi, C.-H. Wong, Angew. Chem. 2001, 113, 1314; Angew. Chem. Int. Ed. 2001, 40, 1274.
16. K. M. Koeller. C.-H. Wong, Chem. Rev. 2000, 100, 4465.
17. X.-S. Ye, C.-H. Wong. J. Org. Chem. 2000, 65, 2410.
18. P. J. Garegg, Adv. Carbohydr. Chem. Biochem. 1997, 52, 179.
19. J. H. van Boom, P. M. Burgers, Tetrahedron Lett. 1976, 4875.
20. H. Yin, W. D'Souza, T. L. Lowary, J. Org. Chem. 2002, 67, 892.