gem-Diamine 1-N-iminosugars of L-fucose-type, the extremely potent L- fucosidase inhibitors

Bioorganic and Medicinal Chemistry

Volumn 8, Issue 2, 2000, Pages 343-352

  Shitara, Eiki ^a   Nishimura, Yoshio ^a   Kojima, Fukiko ^a   Takeuchi, Tomio ^a  

^a INSTITUTE OF MICROBIAL CHEMISTRY   (Japan)

Author keywords

(2S,3S,4R,5R) 2 trifluoroacetamido 5 methylpiperidine 3,4 dial; Cyclic methanediamine; gem Diamine 1 N iminosugar; L fucosidase inhibitor

Indexed keywords

2 TRIFLUOROACETAMIDO 5 METHYLPIPERIDINE 3,4 DIOL; ALPHA LEVO FUCOSIDASE; DIAMINE; ENZYME INHIBITOR; FUCOSE; UNCLASSIFIED DRUG;

ARTICLE; DRUG STRUCTURE; DRUG SYNTHESIS; ENZYME INHIBITION; NONHUMAN; OXIDATION; REACTION ANALYSIS; STEREOCHEMISTRY; STRUCTURE ANALYSIS;

ALPHA-L-FUCOSIDASE; CARBOHYDRATE SEQUENCE; CARBOHYDRATES; DIAMINES; ENZYME INHIBITORS; IMINES; MOLECULAR SEQUENCE DATA; MOLECULAR STRUCTURE; SPECTRUM ANALYSIS;

EID: 0033997821     PISSN: 09680896     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0968-0896(99)00289-8     Document Type: Article

References (30)

1. Karlsson G.B., Butters T.D., Dwek R.A., Platt F.M. J. Biol. Chem. 268:1993;570.
2. Winchester B., Fleet G.W.J. Glycobiology. 2:1992;199.
3. Look G.C., Fotsch C.H., Wong C.-H. Acc. Chem. Res. 26:1993;182.
4. Nishimura, Y. In Studies in Natural Products Chemistry; Atta-ur-Rahman, Ed.; Elsevier: Amsterdam, 1992; Vol. 10, pp 495-583.
5. Nishimura Y., Kudo T., Kondo S., Takeuchi T. J. Antibiot. 47:1994;101.
6. Nishimura, Y. In Studies in Natural Products Chemistry; Atta-ur-Rahman, Ed.; Elsevier: Amsterdam, 1995; Vol. 16, pp 75-121.
7. Cordes E.H., Bull H.G. Chem. Rev. 74:1974;581.
8. Perkins S.J., Johnson L.N., Philips D.C., Dwek R.A. Biochem. J. 193:1981;553.
9. Sinnott M.L. Chem. Rev. 90:1990;1171.
10. Kajimoto T., Liu K.K.-C., Pederson R.L., Zhong Z., Ichikawa Y., Porco J.A. Jr., Wong C.-H. J. Am. Chem. Soc. 113:1991;6187.
11. Ichikawa Y., Igarashi Y., Ichikawa M., Suhara Y. J. Am. Chem. Soc. 120:1998;3007.
12. Nishimura Y., Satoh T., Kondo S., Takeuchi T., Azetaka M., Fukuyasu H., Iizuka Y., Shibahara S. J. Antibiot. 47:1994;840.
13. Satoh T., Nishimura Y., Kondo S., Takeuchi T., Azetaka M., Fukuyasu H., Iizuka Y., Ohuchi S., Shibahara S. J. Antibiot. 49:1996;321.
14. Nishimura Y., Satoh T., Kudo T., Kondo S., Takeuchi T. Bioorg. Med. Chem. 4:1996;96.
15. Nishimura Y., Satoh T., Adachi H., Kondo S., Takeuchi T., Azetaka M., Fukuyasu H., Iizuka Y. J. Am. Chem. Soc. 118:1996;3051.
16. Shitara E., Nishimura Y., Kojima F., Takeuchi T. J. Antibiot. 52:1999;348.
17. Nishimura, Y.; Shitara, E.; Adachi, H.; Takeuchi, T.; Nakajima, M. J. Org. Chem., in press.
18. Lowe J.B., Stoolman L.M., Nair R.P., Larsen R.D., Berhend T.L., Marks R.M. Cell. 63:1990;475.
19. Berg E.L., Robinson M.K., Mansson O., Butcher E.C., Magnani J.L. J. Biol. Chem. 266:1991;14869.
20. Lauri D., Needham L., Martin-Padura I., Dejana E. J. Natl. Cancer Inst. 83:1991;1321.
21. Osborn L., Hession C., Tizard R., Vassallo C., Luhowskyj S., Chi-Rosso G., Lobb R. Cell. 59:1989;1203.
22. Niedbala M.J., Madiyalakan R., Matta K., Crickard K., Sharma M., Bernacki R.J. Cancer Res. 47:1987;4634.
23. Winchester B., Barker C., Baines S., Jacob G.S., Namgoong S.K., Fleet G. Biochem. J. 265:1990;277.
24. 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. USA 1988, 85, 9229.
25. Nishimura Y., Shitara E., Takeuchi T. Tetrahedron Lett. 40:1999;2351.
26. Kudo T., Nishimura Y., Kondo S., Takeuchi T. J. Antibiot. 45:1992;954.
27. Dess D.B., Martin J.C. J. Org. Chem. 48:1983;4155.
28. Mancuso A.J., Huang S.-L., Swern D. J. Org. Chem. 43:1978;2480.
29. Lemieux R.U., Kulling R.K., Bernstein H.J., Schneider W.G. J. Am. Chem. Soc. 80:1958;6098.
30. For a review, see: Mitsunobu, O. Synthesis 1981, 1-28.