A novel approach to the 1-deoxynojirimycin system: Synthesis from sucrose of 2-acetamido-1,2-dideoxynojirimycin, as well as some 2-N-modified derivatives

Carbohydrate Research

Volumn 287, Issue 1, 1996, Pages 49-57

  Gradnig, Günther ^a   Legler, Günter ^b   Stütz, Arnold E ^a  

^a GRAZ UNIVERSITY OF TECHNOLOGY   (Austria)

^b UNIVERSITY OF COLOGNE   (Germany)

Author keywords

1 Deoxynojirimycin; 2 Acetamido 1,2 dideoxynojirimycin; Glycosidase inhibitors; Sucrose

Indexed keywords

1 DEOXYNOJIRIMYCIN; 2 ACETAMIDO 1,2 DIDEOXYNOJIRIMYCIN; 3,4,6 TRI 2 BENZYL 1,5 DIDEOXY 1,5 IMINO MANNITOL; BETA N ACETYLHEXOSAMINIDASE; GLYCOSIDASE INHIBITOR; UNCLASSIFIED DRUG;

AMINATION; ANIMAL CELL; ARTICLE; BINDING KINETICS; CARBOHYDRATE SYNTHESIS; CATTLE; ENZYME INHIBITION; GLYCOPROTEIN SYNTHESIS; HYDROGENATION; INHIBITION KINETICS; NONHUMAN; PRIORITY JOURNAL; PROTEIN MODIFICATION; STRUCTURE ANALYSIS;

EID: 0029974438     PISSN: 00086215     EISSN: None     Source Type: Journal    
DOI: 10.1016/0008-6215(96)00065-1     Document Type: Article

References (26)

1. G. Legler, Adv. Carbohydr. Chem., 48 (1990) 319-384.
2. G.W.J. Fleet, P.W. Smith, R.J. Nash, L.E. Fellows, R.B. Parekh, and T.W. Rademacher, Chem. Lett., (1986) 1051-1054.
3. G.W.J. Fleet, L.E. Fellows, and P.W. Smith, Tetrahedron, 43 (1987) 979-990.
4. M.H.M.G. Schumacher-Wandersleb, S. Petersen, and M.G. Peter, Liebigs Ann. Chem., (1994) 555-561.
5. E. Kappes and G. Legler, J. Carbohydr. Chem., 8 (1989) 371-388.
6. H. Böshagen, F.-R. Heiker, and A.M. Schüller, Carbohydr. Res., 164 (1987) 141-148.
7. M. Kiso, M. Kitagawa, H. Ishida, and A. Hasegawa, J. Carbohydr. Chem., 10 (1991) 25-45.
8. T. Kajimoto, K.K.-C. Liu, R.L. Pederson, Z. Zhong, Y. Ishikawa, J.A. Porco, Jr., and C.-H. Wong, J. Am. Chem. Soc., 113 (1991) 6187-6196.
9. R.H. Furneaux, G.J. Gainsford, G.P. Lynch, and S.C. Yorke, Tetrahedron, 49 (1993) 9605-9612.
10. G. Legler, E. Lüllau, E. Kappes, and F. Kastenholz, Biochim. Biophys. Acta, 1080(2) (1991) 89-95.
11. A.E. Stütz, unpublished results.
12. A. de Raadt and A.E. Stütz, Tetrahedron Lett., 33 (1992) 189-192.
13. W. Zou and W.A. Szarek, Carbohydr. Res., 254 (1994) 25-33; and references cited there.
14. L. Hough and K.S. Mufti, Carbohydr. Res., 25 (1972) 497-503; R.G. Almquist and E.J. Reist, Carbohydr. Res., 46 (1976) 33-41; R.G. Almquist and E.J. Reist, J. Med. Chem., 20 (1977) 1246-1250; R. Khan, B.C. Lal, K.S. Mufti, and M.R. Jenner, Carbohydr. Res., 78 (1) (1980) 185-189; N.K. Sharma, J.L. Norula, and S.K. Mattey, J. Ind. Chem. Soc., 59 (1982) 385-388.
15. L. Hough and K.S. Mufti, Carbohydr. Res., 25 (1972) 497-503; R.G. Almquist and E.J. Reist, Carbohydr. Res., 46 (1976) 33-41; R.G. Almquist and E.J. Reist, J. Med. Chem., 20 (1977) 1246-1250; R. Khan, B.C. Lal, K.S. Mufti, and M.R. Jenner, Carbohydr. Res., 78 (1) (1980) 185-189; N.K. Sharma, J.L. Norula, and S.K. Mattey, J. Ind. Chem. Soc., 59 (1982) 385-388.
16. L. Hough and K.S. Mufti, Carbohydr. Res., 25 (1972) 497-503; R.G. Almquist and E.J. Reist, Carbohydr. Res., 46 (1976) 33-41; R.G. Almquist and E.J. Reist, J. Med. Chem., 20 (1977) 1246-1250; R. Khan, B.C. Lal, K.S. Mufti, and M.R. Jenner, Carbohydr. Res., 78 (1) (1980) 185-189; N.K. Sharma, J.L. Norula, and S.K. Mattey, J. Ind. Chem. Soc., 59 (1982) 385-388.
17. L. Hough and K.S. Mufti, Carbohydr. Res., 25 (1972) 497-503; R.G. Almquist and E.J. Reist, Carbohydr. Res., 46 (1976) 33-41; R.G. Almquist and E.J. Reist, J. Med. Chem., 20 (1977) 1246-1250; R. Khan, B.C. Lal, K.S. Mufti, and M.R. Jenner, Carbohydr. Res., 78 (1) (1980) 185-189; N.K. Sharma, J.L. Norula, and S.K. Mattey, J. Ind. Chem. Soc., 59 (1982) 385-388.
18. L. Hough and K.S. Mufti, Carbohydr. Res., 25 (1972) 497-503; R.G. Almquist and E.J. Reist, Carbohydr. Res., 46 (1976) 33-41; R.G. Almquist and E.J. Reist, J. Med. Chem., 20 (1977) 1246-1250; R. Khan, B.C. Lal, K.S. Mufti, and M.R. Jenner, Carbohydr. Res., 78 (1) (1980) 185-189; N.K. Sharma, J.L. Norula, and S.K. Mattey, J. Ind. Chem. Soc., 59 (1982) 385-388.
19. M. Vaultier, N. Knouzi, and R. Carrie, Tetrahedron Lett., 24 (1983) 763-764.
20. G.W.J. Fleet, N.G. Ramsden, and D.R. Witty, Tetrahedron, 45 (1989) 327-336; M. Kiso, H. Katagiri, H. Furui, and A. Hasegawa, J. Carbohydr. Chem., 11 (1992) 627-644; H. Ardron, T.D. Butters, F.M. Platt, M.R. Wormald, R.A. Dwek, G.W.J. Fleet, and G.S. Jacob, Tetrahedron: Asymm., 4 (1993) 2011-2024.
21. G.W.J. Fleet, N.G. Ramsden, and D.R. Witty, Tetrahedron, 45 (1989) 327-336; M. Kiso, H. Katagiri, H. Furui, and A. Hasegawa, J. Carbohydr. Chem., 11 (1992) 627-644; H. Ardron, T.D. Butters, F.M. Platt, M.R. Wormald, R.A. Dwek, G.W.J. Fleet, and G.S. Jacob, Tetrahedron: Asymm., 4 (1993) 2011-2024.
22. G.W.J. Fleet, N.G. Ramsden, and D.R. Witty, Tetrahedron, 45 (1989) 327-336; M. Kiso, H. Katagiri, H. Furui, and A. Hasegawa, J. Carbohydr. Chem., 11 (1992) 627-644; H. Ardron, T.D. Butters, F.M. Platt, M.R. Wormald, R.A. Dwek, G.W.J. Fleet, and G.S. Jacob, Tetrahedron: Asymm., 4 (1993) 2011-2024.
23. G. Legler, A.E. Stütz, and H. Immich, Carbohydr. Res., 272 (1995) 17-30.
24. C. Hansch and S.M. Anderson, J. Org. Chem., 32 (1965) 2583-2586.
25. The Merck Index, 11th ed., Merck, Rahway, NJ (1989).
26. P.G. Walker in E.A. Balsz and R.W. Jeanloz (Eds.), The Amino Sugars, Vol. IIB, Academic Press, New York, pp. 155-179.