Synthesis of 5-Thio-L-fucose-Containing Disaccharides, as Sequence-Specific Inhibitors, and 2′-Fucosyllactose, as a Substrate of α-L-Fucosidases

Journal of Organic Chemistry

Volumn 62, Issue 4, 1997, Pages 992-998

  Izumi, Masayuki ^a,b   Tsuruta, Osamu ^a   Harayama, Satoru ^a   Hashimoto, Hironobu ^a  

^a TOKYO INSTITUTE OF TECHNOLOGY   (Japan)

^b JOHNS HOPKINS UNIVERSITY SCHOOL OF MEDICINE   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

DISACCHARIDE; FUCOSIDASE INHIBITOR; GLYCOSIDASE INHIBITOR; UNCLASSIFIED DRUG;

ANIMAL TISSUE; ARTICLE; BACILLUS; CARBOHYDRATE SYNTHESIS; CATTLE; CONTROLLED STUDY; DRUG SYNTHESIS; ENZYME INHIBITION; EPIDIDYMIS; IN VITRO STUDY; NONHUMAN; REACTION ANALYSIS;

EID: 0030972056     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo961725h     Document Type: Article

References (31)

1. (a) Fuhrmann, U.; Bause, E.; Ploegh, H. Biochem. Biophys. Acta 1985, 825, 95.
2. (b) Elbein, A. D. Annu. Rev. Biochem. 1987, 56, 497. Elbein, A. D. FASEB J. 1991, 5, 3055.
3. (b) Elbein, A. D. Annu. Rev. Biochem. 1987, 56, 497. Elbein, A. D. FASEB J. 1991, 5, 3055.
4. Truscheit, E.; Frommer, W.; Junge, B.; Müller, L.; Schmidt, D. D.; Wingender, W. Angew. Chem., Int. Ed. Engl. 1981, 20, 744.
5. (a) Schwarz, P. M.; Elbein, A. D. J. Biol. Chem., 1985, 260, 14452.
6. (b) Gruters, R. A.; Neefjes, J. J.; Tersmette, M.; De Goede, R. E. Y.; Tulp, A.; Huisman, H. G.; Miedena, F.; Ploegh, H. L. Nature 1987, 330, 74.
7. (c) Karpas, A.; Fleet, G. W. J.; Dwek, R. A.; Petursson, S.; Namgoong, S. K.; Ramsden, N. G.; Jacob, G. S.; Rademacher, T. W. Proc. Natl. Acad. Sci. U.S.A., 1988, 85, 9229.
8. (a) Humphries, M. J.; Matsumoto, K.; White, S. L.; Olden, K. Cancer Res. 1986, 46, 5215.
9. Defaye, J.; Gelas, J. In Studies in Natural Product Chemistry; Atta-ur-Rahman, Ed.; Elsevier: Amsterdam, 1991, Vol. 8, p 315.
10. Orgeret, C.; Seillier, E.; Gautier, C.; Defaye, J.; Driguez, H. Carbohydr. Res., 1992, 224, 29.
11. (a) DeSantis, R.; Pinto, M. R. Gamete Interaction in Ascidians: Sperm Binding and Penetration Through the Vitelline Coat. In Mechanism of Fertilization: Plants to Humans; Dale, B., Ed.; Springer-Verlag: Berlin, 1990; p 297.
12. (b) Hoshi, M.; DeSantis, R.; Pinto, M. R.; Cotelli, F.; Rosati, F. Zool. Sci., 1985, 2, 65.
13. Huang, T. F., Jr.; Ohzu, E.; Yanagimachi, R. Gamete Res., 1982, 5, 355.
14. Hashimoto, H.; Shimada, K.; Horito, S. Tetrahedron: Asymmetry 1994, 5, 2351.
15. Hashimoto, H.; Fujimori, T.; Yuasa, H. J. Carbohydr. Chem., 1990, 9, 683.
16. Hashimoto, H.; Izumi, M. Tetrahedron Lett., 1993, 31, 4949.
17. Schmidt, R.; R. Kinzy, W. Adv. Carbohydr. Chem. Biochem., 1994, 50, 21.
18. Izumi, M.; Tsuruta, O.; Hashimoto, H. Carbohydr. Res., 1996, 280, 287.
19. Sugimoto, M.; Numata, M.; Koike, K.; Nakahara, Y.; Ogawa, T. Carbohydr. Res., 1986, 156, c1.
20. Roy, R.; Jennings, H. J. Carbohydr. Res., 1983, 112, 63.
21. Kosma, P.; Bahnmüller, R.; Schulz, G.; Brade, H. Carbohydr. Res., 1990, 208, 37.
22. Hasegawa, A.; Ozaki, M.; Kiso, M.; Azuma, I. J. Carbohydr. Chem., 1984, 3, 331.
23. Nashed, N. M. Carbohydr. Res., 1979, 71, 299-304.
24. Petitou, M.; Duchaussoy, P. Lederman, I.; Choay, J.; Sinaÿ. P.; Jacquinet, J.-C.; Torri, G. Carbohydr. Res., 1986, 147, 221.
25. Tailler, D.; Jacquinet, J.-C.; Noirot, A.-M.; Beau, J.-M. J. Chem. Soc., Perkin Trans. 1, 1992, 3163.
26. van Boeckel, C. A. A.; van Aelst, S. F.; Beetz, T. Recl. Trav. Chim. Pays-Bas, 1983, 102, 415.
27. Helferich, B.; Zirner, J. Chem. Ber., 1962, 95, 2604.
28. Yoshino, T.; Ishido, Y. 17th Japanese Carbohydrate Symposium, July 18-20, 1995, Kyoto: Abstract p 170.
29. Sphor, U.; Paszkiwicz-Hnatiw, E.; Morishima, N.; Lemieux, R. U. Can J. Chem., 1992, 70, 254 and references therein.
30. Tsay, G. C.; Daeson, G. Anal. Biochem., 1977, 78, 423.
31. Compound 1 showed 7% inhibition at 5 mM.