Asymmetric synthesis of potent glycosidase and very potent α-mannosidase inhibitors: 4-amino-4-deoxy-L-erythrose and 4-amino-4,5-dideoxy-L-ribose

Tetrahedron

Volumn 59, Issue 4, 2003, Pages 543-553

  Behr, Jean Bernard ^a,b   Chevrier, Carine ^a   Defoin, Albert ^a   Tarnus, C éline ^a   Streith, Jacques ^a  

^a Ecole Nationale Superieure de Chimie de Mulhouse   (France)

^b UNIVERSITÉ DE REIMS CHAMPAGNE ARDENNE   (France)

Author keywords

mannosidase inhibitor; 3,4 dihydroxypyrrolines; Amino sugars; Aminoalditols; Glycosidase inhibitors

Indexed keywords

4 AMINO 4 DEOXY LEVO ERYTHROSE; 4 AMINO 4,5 DIDEOXY LEVO RIBOSE; ALPHA GALACTOSIDASE; ALPHA MANNOSIDASE; BETA GALACTOSIDASE; BETA GLUCOSIDASE; GLYCOSIDASE; UNCLASSIFIED DRUG;

ARTICLE; ASYMMETRIC SYNTHESIS; CARBON NUCLEAR MAGNETIC RESONANCE; DIELS ALDER REACTION; DRUG SYNTHESIS; INFRARED SPECTROSCOPY; PRIORITY JOURNAL; PROTON NUCLEAR MAGNETIC RESONANCE;

BETULACEAE;

EID: 0037454742     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(02)01512-0     Document Type: Article

References (49)

1. Elbein A.D. Ann. Rev. Biochem. 56:1987;497-534.
2. Legler G. Adv. Carbohydr. Chem. Biochem. 48:1990;319-384.
3. Winchester B., Fleet G.W.J. Glycobiology. 2:1992;199-210.
4. Asano N., Nash R.J., Molyneux R.J., Fleet G.W.J. Tetrahedron: Asymmetry. 11:2000;1645-1680.
5. Sinnott M.E. Chem. Rev. 90:1990;1171-1202.
6. Zechel D.L., Withers S.G. Acc. Chem. Res. 33:2000;11-18.
7. Paulsen H., Brüning J., Heyns K. Chem. Ber. 103:1970;1621-1630.
8. Paulsen H., Propp K., Brüning J. Chem. Ber. 102:1969;469-487.
9. Shibata T., Nakayama O., Tsurumi Y., Okuhara M., Terano H., Kohsaka M. J. Antibiot. 41:1988;296-301.
10. Kayakiri H., Nakamura K., Takase S., Setoi H., Uchida I., Terano H., Hashimoto M., Tada T., Koda S. Chem. Pharm. Bull. 39:1991;2807-2812.
11. Kim Y.J., Takatsuki A., Kogoshi N., Kitahara T. Tetrahedron. 55:1999;8353-8364.
12. Tsujii E., Muroi M., Shiragami N., Takatsuki A. Biochem. Biophys. Res. Commun. 220:1996;549-566.
13. Witte J.F., McClard R.W. Tetrahedron Lett. 32:1991;3927-3930.
14. Provencher L., Steensma D.H., Wong C.-H. Bioorg. Med. Chem. 2:1994;1179-1188.
15. Wong C.-H., Provencher L., Porco J.A. Jr., Jung S.-H., Wang Y.-F., Chen L., Wang R., Steensma D., J. Org. Chem. 60:1995;1492-1501.
16. Joubert M., Defoin A., Tarnus C., Streith J. Synlett. 2000;1366-1368.
17. Behr J.-B., Defoin A., Mahmood N., Streith J. Helv. Chim. Acta. 78:1995;1166-1177.
18. Behr J.-B., Defoin A., Pires J., Streith J., Macko L., Zehnder M. Tetrahedron. 52:1996;3283-3302.
19. Bach P., Bols M. Tetrahedron Lett. 40:1999;3461-3464.
20. Zhang D., Gosh A., Süling C., Miller M.J. Tetrahedron Lett. 37:1996;3799-3802.
21. Defoin A., Fritz H., Geffroy G., Streith J. Helv. Chim. Acta. 71:1988;1642-1658.
22. Paulsen H., Todt K. Chem. Ber. 100:1967;3385-3396.
23. (a) Defoin A., Sarazin H., Streith J. Tetrahedron. 53:1997;13769-13782.
24. (b) Defoin A., Sarazin H., Streith J. Tetrahedron. 53:1997;13783-13796.
25. Defoin A., Pires J., Streith J. Helv. Chim. Acta. 74:1991;1653-1670.
26. Defoin A., Pires J., Streith J. Synlett. 1991;417-419.
27. Keck G.E., Wager T.T., McHardy S.F. Tetrahedron. 55:1999;11755-11772.
28. Keck G.E., Fleming S., Nickell D., Weider P. Synth. Commun. 9:1979;281-286.
29. Bierer, L. Dissertation. PhD Thesis, Stuttgart, Germany, 1999.
30. Palmer A.M., Jäger V. Eur. J. Org. Chem. 2001;2547-2558. This enantiomer was found inactive against glycosidases.
31. Paulsen H. Liebigs Ann. Chem. 683:1965;187-198.
32. Kondo K.-I., Adachi H., Shirata E., Kojima F., Nishimura Y. Bioorg. Med. Chem. 9:2001;1091-1095.
33. Popowycz F., Gerber-Lemaire S., Demange R., Rodriguez-Garcia E., Carmona Asenjo A.T., Robina I., Vogel P. Bioorg. Med. Chem. Lett. 11:2001;2489-2493.
34. Ogawa S., Morikawa T. Bioorg. Med. Chem. Lett. 9:1999;1499-1504.
35. Nishimura Y., Umezawa Y., Adachi H., Kondo S., Takeuchi T. J. Org. Chem. 61:1996;480-488.
36. Ogawa S., Morikawa T. Bioorg. Med. Chem. Lett. 10:2000;1047-1050.
37. Tropea J.E., Kaushal G.P., Pastuszak I., Mitchell M., Aoyagi T., Molineux R.J., Elbein A.D. Biochem. 29:1990;10062-10069.
38. Cho S.J., Ling R., Kim A., Mariano P.S. J. Org. Chem. 65:2000;1574-1577.
39. Farr R.A., Peet N.P., Kang M.S. Tetrahedron Lett. 31:1990;7109-7112.
40. Schneider M.J., Ungemach F.S., Broquist H.P., Harris T.M. Tetrahedron. 39:1983;29-32.
41. Tulsiani D.R.P., Broquist H.P., Touster O. Arch. Biochem. Biophys. 236:1985;427-434.
42. Fleet G.W.J., Smith P.W., Evans S.V., Fellows L.E. J. Chem. Soc, Chem. Commun. 1984;1240-1241.
43. Carpino L.A., Giza C.A., Carpino B.A. J. Org. Chem. 81:1959;955-957.
44. Dang H.-S., Davies A.G. J. Chem. Soc., Perkin Trans. 2. 1991;721-734.
45. VanRheenen V., Kelly R.C., Cha D.Y. Tetrahedron Lett. 17:1976;1973-1976.
46. Akashi K., Palermo R.E., Sharpless K.B. J. Org. Chem. 43:1978;2063-2066.
47. Lundblad G., Bjare U., Lybing S., Måhlén A. Int. J. Biochem. 15:1983;835.
48. La Y.-T. J. Biol. Chem. 242:1967;5474-5480.
49. Segel I.H. Enzyme Kinetics. 1975;Wiley, New York. pp 109-144.