Synthesis and activity of 1-N-iminosugar inhibitors, siastatin B analogues for α-N-acetylgalactosaminidase and β-N-acetylglucosaminidase

Bioorganic and Medicinal Chemistry

Volumn 4, Issue 1, 1996, Pages 91-96

  Nishimura, Yoshio ^a   Satoh, Takahiko ^a   Kudo, Toshiaki ^a   Kondo, Shinichi ^a   Takeuchi, Tomio ^a  

^a INSTITUTE OF MICROBIAL CHEMISTRY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

STREPTOMYCES;

ALPHA N ACETYLGALACTOSAMINIDASE; CARBOHYDRATE DERIVATIVE; GLUCOSAMINIDASE; GLYCOSIDASE INHIBITOR; SIASTATIN B; UNCLASSIFIED DRUG;

ANIMAL TISSUE; ARTICLE; CATTLE; CHICKEN; CONTROLLED STUDY; DRUG SYNTHESIS; ENZYME INHIBITION; EPIDIDYMIS; LIVER; NONHUMAN; YEAST;

ACETYLGLUCOSAMINIDASE; ALPHA-N-ACETYLGALACTOSAMINIDASE; ANIMALS; CATTLE; CHICKENS; ENZYME INHIBITORS; EPIDIDYMIS; HEXOSAMINIDASES; IMINO PYRANOSES; LIVER; MALE; PIPERIDINES; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 0029916263     PISSN: 09680896     EISSN: None     Source Type: Journal    
DOI: 10.1016/0968-0896(95)00166-2     Document Type: Article

References (29)

1. (a) Look, G. C.; Fotsch, C. H.; Wong, C.-H. Acc. Chem. Res. 1993, 26, 182;
2. (b) Nishimura, Y. Studies in Natural Products Chemistry; Atta-ur-Rahman, Ed.; Elsevier: Amsterdam, 1992; Vol. 10, pp 495-583;
3. (c) Winchester, B.; Fleet, G. W. Glycobiology 1992, 2, 199.
4. Umezawa, H.; Aoyagi, T.; Komiyama, T.; Morishima, H.; Hamada, M.; Takeuchi, T. J. Antibiotics 1974, 27, 963.
5. (a) Nishimura, Y.; Wang, W.; Kondo, S.; Aoyagi, T.; Umezawa, H. J. Am. Chem. Soc. 1988, 110, 7249;
6. (b) Nishimura, Y.; Wang, W.; Kudo, T.; Kondo, S. Bull. Chem. Soc. Jpn. 1992, 65, 978;
7. (c) Kudo, T.; Nishimura, Y.; Kondo, S.; Takeuchi, T. J. Antibiotics 1992, 45, 954;
8. (d) Nishimura, Y.; Kudo, T.; Kondo, S.; Takeuchi, T. J. Antibiotics 1992, 45, 963;
9. (e) Nishimura, Y.; Kudo, T.; Umezawa, Y.; Kondo, S.; Takeuchi, T. Nat. Prod. Lett. 1992, 1, 39;
10. (f) Nishimura, Y.; Kudo, T.; Umezawa, Y.; Kondo, S.; Takeuchi, T. Nat. Prod. Lett. 1992, 1, 33;
11. (g) Kudo, T.; Nishimura, Y.; Kondo, S.; Takeuchi, T. J. Antibiotics 1992, 45, 1662;
12. (h) Kudo, T.; Nishimura, Y.; Kondo, S.; Takeuchi, T. J. Antibiotics 1993, 46, 300;
13. (i) Nishimura, Y.; Umezawa, Y.; Kondo, S.; Takeuchi, T.; Mori, K.; Kijima-Suda, I.; Tomita, K.; Sugawara, K.; Nakamura, K. J. Antibiotics 1993, 46, 1883;
14. (j) Nishimura, Y.; Kudo, T.; Kondo, S.; Takeuchi, T.; Tsuruoka, T.; Fukuyasu, H.; Shibahara, S. J. Antibiotics 1994, 47, 101;
15. (k) Nishimura, Y.; Satoh, S.; Kondo, S.; Takeuchi, T.; Azetaka, M.; Fukuyasu, H.; Iizuka, Y.; Shibahara, S. J. Antibiotics 1994, 47, 840;
16. (l) Satoh, T.; Nishimura, Y.; Kondo, S.; Takeuchi, T. Carbohyd. Res., in press;
17. (m) Nishimura, Y. Studies in Natural Products Chemistry; Atta-ur-Rahamn, Ed.; Elsevier: Amsterdam, 1995; Vol. 16, pp. 75-123.
18. Very recently, 1-N-iminosugar inhibitors of glucosidase have been synthesized: (a) Jespersen, T. M.; Dong, W.; Sierks, M. R.; Skrydstrup, T.; Lundt, I.; Bols, M. Angew. Chem. Int. Ed. Engl. 1994, 33, 1778;
19. (b) Ichikawa, M.; Igarashi, Y.; Ichikawa, Y. Tetrahedron Lett. 1995, 36, 1767.
20. (a) Dennis, J. W.; Laferte, S.; Waghorne, C.; Breitman, M. L.; Kerbel, R. S. Science 1987, 236, 582;
21. (b) Dennis, J. W. Cancer Surveys 1988, 7, 573.
22. Kim, S. C.; Singh, A. N.; Rausher, F. J. Biol. Chem. 1988, 263, 10151.
23. Halvorson, H. O.; Ellias, L. Biochim. Biophys. Acta 1958, 30, 28.
24. Kobayashi, A. Agr. Biol. Chem. 1962, 26, 203.
25. Li, Y.-T. J. Biol. Chem. 1967, 242, 5474.
26. Craven, G. R.; Steers, Jr., E.; Anfinsen, C. B. J. Biol. Chem. 1965, 240, 2468.
27. Stahl, P. P. D.; Fishman, W. H. Methods of Enzymatic Analysis; Voigt, K. D., Ed.; Academic, New York, 1974; Vol. 4, pp 246-256.
28. Uda, Y.; Li, S.-C.; Li, Y.-T. J. Biol. Chem. 1977, 252, 5194.
29. Aoyagi, T.; Suda, H.; Uotani, K.; Kojima, F.; Aoyama, T.; Horiguchi, K.; Hamada, M.; Takeuchi, T. J. Antibiotics 1992, 45, 1404.