Synthesis of N-acetylglucosamine-derived nagstatin analogues and their evaluation as glycosidase inhibitors

Helvetica Chimica Acta

Volumn 88, Issue 1, 2005, Pages 10-22

  Terinek, Miroslav ^a   Vasella, Andrea ^a  

^a ETH ZURICH   (Switzerland)

Author keywords

[No Author keywords available]

Indexed keywords

ALCOHOLS; BIOLOGICAL ORGANS; CONDENSATION; ENZYME INHIBITION; ESTERS; HYDROLYSIS; SYNTHESIS (CHEMICAL);

BOVINE KIDNEY; MICROMOLAR INHIBITORS; NAGSTATIN;

DERIVATIVES;

ACETIC ACID DERIVATIVE; ACID; ALCOHOL DERIVATIVE; AZIDE; BETA GLUCOSIDASE; BETA MANNOSIDASE; BIPHENYL DERIVATIVE; ESTER DERIVATIVE; GLYCOSIDASE INHIBITOR; IMIDAZOLE DERIVATIVE; LACTAM DERIVATIVE; N ACETYLGLUCOSAMINE; NAGSTATIN; PHOSPHORUS DERIVATIVE; SILANE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; BEAN; CALDOCELLUM SACCHAROLYTICUM; CHEMICAL STRUCTURE; COW; DEOXYGENATION; DESILYLATION; HYDROLYSIS; MITSUNOBU REACTION; NONHUMAN; POLYMERIZATION; PRIORITY JOURNAL; REACTION ANALYSIS; SNAIL; SUBSTITUTION REACTION; THERMOPHILIC BACTERIUM;

EID: 14644432504     PISSN: 0018019X     EISSN: None     Source Type: Journal    
DOI: 10.1002/hlca.200490286     Document Type: Article

References (34)

1. T. Aoyagi, H. Suda, K. Uotani, F. Kojima, T. Aoyama, K. Horiguchi, M. Hamada, T. Takeuchi, J. Antibiot. 1992, 45, 1404.
2. K. Tatsuta, S. Miura, S. Ohta, H. Gunji, J. Antibiot. 1995, 48, 286.
3. K. Tatsuta, S. Miura, Tetrahedron Lett. 1995, 36, 6721.
4. K. Tatsuta, S. Miura, H. Gunji, Bull. Chem. Soc. Jpn. 1997, 70, 427.
5. T. Aoyama, H. Naganawa, H. Suda, K. Uotani, T. Aoyagi, T. Takeuchi, J. Antibiot. 1992, 45, 1557.
6. N. Panday, A. Vasella, Synthesis 1999, 1459.
7. N. Panday, Y. Canac, A. Vasella, Helv. Chim. Acta 2000, 83, 58.
8. M. Terinek, A. Vasella, Helv. Chim. Acta 2003, 86, 3482.
9. M. Terinek, A. Vasella, Helv. Chim. Acta, 2004, 87, 3035.
10. N. Panday, A. Vasella, Helv. Chim. Acta 2000, 83, 1205.
11. B. Schlesier, V. H. Nong, C. Horstmann, M. Hennig, J. Plant Physiol. 1996, 747, 665.
12. M. Hennig, J. N. Jansonius, A. C. Terwisscha van Scheltinga, B. W. Dijkstra, B. Schlesier, J. Mol. Biol. 1995, 254, 237.
13. K. Tatsuta, S. Miura, S. Ohta, H. Gunji, Tetrahedron Lett. 1995, 36, 1085.
14. M. Terinek, A. Vasella, Tetrahedron: Asymmetry, in press.
15. N. Panday, M. Meyyappan, A. Vasella, Helv. Chim. Acta 2000, 83, 513.
16. E. J. Corey, A. Venkateswarlu, J. Am. Chem. Soc. 1972, 94, 6190.
17. E. J. Corey, D. H. Hua, B.-C. Pan, S. P. Seitz, J. Am. Chem. Soc. 1982, 104, 6818.
18. O. Mitsunobu, Synthesis 1981, 1.
19. H. Loibner, E. Zbiral, Helv. Chim. Acta 1976, 59, 2100.
20. H. Loibner, E. Zbiral, Helv. Chim. Acta 1977, 60, 417.
21. E. Brunn, R. Huisgen, Angew. Chem., Int. Ed. 1969, 8, 513.
22. A. S. Thompson, G. R. Humphrey, A. M. DeMarco, D. J. Mathre, E. J. J. Grabowski, J. Org. Chem. 1993, 58, 5886.
23. N. Panday, T. Granier, A. Vasella, Helv. Chim. Acta 1998, 81, 475.
24. H. Bayley, D. N. Standring, J. R. Knowles, Tetrahedron Lett. 1978, 19, 3633.
25. M. Terinek, A. Vasella, Helv. Chim. Acta 2004, 87, 719.
26. T. D. Heightman, P. Ermert, D. Klein, A. Vasella, Helv. Chim. Acta 1995, 78, 514.
27. I. H. Segel, 'Enzyme Kinetics', John Wiley & Sons, New York, 1975.
28. H. Wolff, Org. React. 1955, 3, 327.
29. E. C. K. Lai, S. G. Withers, Biochemistry 1994, 33, 14743.
30. M. Böhm, A. Vasella, Helv. Chim. Acta 2004, 87, 2566.
31. H. Lineweaver, D. Burk, J. Am. Chem. Soc. 1934, 56, 658.
32. A. J. Pope, N. Mian, D. G. Herries, FEBS Lett. 1978, 93, 174.
33. A. R. Plant, J. E. Oliver, M. L. Patchett, R. M. Daniel, H. W. Morgan, Arch. Biochem. Biophys. 1988, 262, 181.
34. C. Blüchel, C. V. Ramana, A. Vasella, Helv. Chim. Acta 2003, 86, 2998.