Synthesis of CMP-sialic acid mimics that have 5-fluorouracil for cytosine and the C-terminal's peptide bond for the phosphate group: Targeting inhibitors of sialyltransferases

Heterocycles

Volumn 63, Issue 4, 2004, Pages 779-784

  Nakahara, Shinji ^a   Tanaka, Toru ^a   Noguchi, Kazuharu ^b   Nozaki, Kenji ^b   Tsuji, Shuichi ^c   Miura, Tsuyoshi ^d   Kajimoto, Tetsuya ^a  

^a TOKYO UNIVERSITY OF AGRICULTURE AND TECHNOLOGY   (Japan)

^b TAIHO PHARMACEUTICAL CO LTD   (Japan)

^c OCHANOMIZU UNIVERSITY   (Japan)

^d NOGUCHI INSTITUTE   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

CYTIDINE PHOSPHATE; CYTOSINE; FLUOROURACIL; SIALIC ACID; SIALYLTRANSFERASE;

ALDOL REACTION; ARTICLE; CATALYSIS; ENZYME INHIBITOR INTERACTION; REACTION ANALYSIS; SYNTHESIS;

EID: 1842524119     PISSN: 03855414     EISSN: None     Source Type: Journal    
DOI: 10.3987/com-04-10009     Document Type: Article

References (25)

1. For example, In Essential of Glycobiology, ed. by A. Varki, R. Cummings, J. Esko, G. Freeze, and J. Marth, Cold Spreing Harbor Lab. Press 1999. M. E. Taylor and K. Drickamer In Introduction to Glycobiology, Oxford Univ. Press 2002.
2. For example, In Essential of Glycobiology, ed. by A. Varki, R. Cummings, J. Esko, G. Freeze, and J. Marth, Cold Spreing Harbor Lab. Press 1999. M. E. Taylor and K. Drickamer In Introduction to Glycobiology, Oxford Univ. Press 2002.
3. For example, In Handbook of Glycosyltransferases and Related Genes, ed. by N. Taniguchi, K. Honke, and M. Fukuda, Springer-Verlag, 2002.
4. (a) P. N. Schroeder and A. Giannis, Angew. Chem., Int. Ed., 1999, 38, 1379.
5. (b) B. Muller, C. Schaub, and R. R. Schmidt, ibid., 1998, 37, 2893.
6. (c) M. Imamura and H. Hashimoto, Chem. Lett., 1996, 1087.
7. For example, nikkomycin Z, an analog of UDP-N-acetyl-D-glucosamine, also has a C-terminal peptide bond for the phosphate group and exhibits potent inhibitory activity toward a N-acetyl-D-glucosaminyltransferase. See also (a) W. A. Konig, H. Hahn, R. Rathman, W. Hass, A. Keckeisen, H. Hagenmaier, C. Bormann, W. Dehler, R. Kurth, and H. Zahner, Liebig Ann. Chem., 1986, 407.
8. (b) A. K. Saksena, R. G. Lovey, V. M. Girijavallabhan, H. Guzik, and A. K. Ganguly, Tetrahedron Lett., 1993, 34, 3267.
9. T. Tanaka, M. Ozawa, T. Miura, T. Inazu, S. Tsuji, and T. Kajimoto, Synlett, 2001, 1487.
10. (a) V. P. Vassilev, T. Uchiyama, T. Kajimoto, and C.-H. Wong, Tetrahedron Lett., 1995, 36, 4081.
11. (b) Idem, ibid., 1995, 36, 5063.
12. (c) K. Shibata, K. Shingu, V. P. Vassilev, K. Nishide, T. Fujita, M. Node, T. Kajimoto, and C.-H. Wong, ibid., 1996, 37, 2791.
13. (d) M. Fujii, T. Miura, T. Kajimoto, and Y. Ida, Synlett, 2000, 1046.
14. (e) K. Nishide, K. Shibata, T. Fujita, T. Kajimoto, and C.-H. Wong, Heterocycles, 2000, 52, 1191.
15. (f) T. Miura and T. Kajimoto, Chirality, 2001, 577.
16. I. Kijima-Suda, Y. Miyamoto, S. Toyoshima, M. Itoh, and T. Osawa, Cancer Res., 1986, 46, 858.
17. 30 reverse phase column was purchased from Nomura Chemicals Co., Ltd., under the trade name "Develosil 30".
18. 3) δ: 1.20 (6H, t, J = 7.0 Hz), 3.53, 3.76 (each 2H, q, J = 7.0 Hz), 3.76 (2H, d, J = 5.0 Hz), 4.60 (1H, t, J = 5.0 Hz), 7.38 (1H, d, J = 6.0 Hz).
19. (a) A. Saeed and D. W. Yong, Tetrahedron, 1992, 48, 2507.
20. (b) T. Kaneko and T. Inui, Bull. Chem. Soc., Jpn., 1961, 82, 1075.
21. W. Konig and R. Geiger, In Peptides; ed. by E. Scoffone, North-Holland Pub. Co., Amsterdam, 1969, 17.
22. 19F, 806.7.
23. 19F, 806.7.
24. 2O) δ: 1.64 (1H, t, J = 12.5 Hz, H-3ax), 1.83 (3H, s, Ac), 2.60 (1H, dd, J = 5.0, 12.5 Hz, H-3eq), 4.10-4.22 (2H, m, H-α and γ), 3.30-4.10 (10H, m), 4.25 (1H, dt, J = 9.0, 3.0 Hz, H-β), 7.72 (1H, d, J = 6.0 Hz, 5FU H-6).
25. 2O) δ: 1.53 (1H, dd, J = 11.0, 13.0 Hz, H-3ax), 1.87 (3H, s, Ac), 2.29 (1H, dd, J = 5.0, 13.0 Hz, H-3eq), 3.30-3.95 (9H, m), 4.05 (2H, m), 4.18 (1H, dd, J = 4.5, 14.0 Hz, H-γ), 4.22 (1H, dd, J = 3.0, 9.0 Hz, H-β), 7.46 (1H, d, J = 6.0 Hz, 5-FU H-6).