Synthesis, conformational studies and mannosidase stability of a mimic of 1,2-mannobioside

European Journal of Organic Chemistry

Volumn , Issue 24, 2004, Pages 5119-5225

  Mari, Silvia ^b   Posteri, Helena ^a   Marcou, Gilles ^a   Potenza, Donatella ^a   Micheli, Fabrizio ^c   Cañada, F Javier ^b   Jimenez Barbero, Jesus ^b   Bernardi, Anna ^a  

^a UNIVERSITY OF MILAN   (Italy)

^b CENTRO DE INVESTIGACIONES BIOLÓGICAS   (Spain)

^c GSK   (Italy)

Author keywords

Carbohydrate mimics; Conformational analysis; Mannobioside

Indexed keywords

1,2 MANNOBIOSIDE; 5 (ALPHA MANNOSYLOXY)CYCLOHEXANE 1,2 DICARBOXYLATE; CARBOHYDRATE; DICARBOXYLIC ACID DERIVATIVE; MANNOSIDASE; UNCLASSIFIED DRUG;

ARTICLE; CARBOHYDRATE ANALYSIS; CARBOHYDRATE SYNTHESIS; CHEMICAL BINDING; CONFORMATION; ENERGY; MOLECULAR MODEL; MOLECULAR STABILITY; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; STRUCTURE ANALYSIS;

EID: 11144314181     PISSN: 1434193X     EISSN: None     Source Type: Journal    
DOI: 10.1002/ejoc.200400520     Document Type: Article

References (37)

1. P. Sears, C. H. Wong, Angew. Chem. 1999, 111, 2446-2471; Angew. Chem. Int. Ed. 1999, 38, 2300-2324, and references cited therein.
2. P. Sears, C. H. Wong, Angew. Chem. 1999, 111, 2446-2471; Angew. Chem. Int. Ed. 1999, 38, 2300-2324, and references cited therein.
3. R. Thomson, M. von Izstein, in Carbohydrate Based Drug Discovery (Ed.: C. H. Wong), 2004, vol. 2, pp. 831-861.
4. R. Horstkorte, O. T. Keppler, W. Reutter, in Carbohydrate Based Drug Discoverv (Ed.: C. H. Wong), 2004, vol. 2, pp. 863-873.
5. A. Bernardi, D. Arosio, L. Manzoni, F. Micheli, A. Pasquarello, P. Seneci, J. Org. Chem. 2001, 66, 6209-6216.
6. A. Bernardi, P. Brocca, A. Checchia, S. Sonnino, F. Zuccotto, J. Am. Chem. Soc. 1999, 121, 2032-2036.
7. A. Bernardi, D. Arosio, S. Sonnino, Neurochem. Res. 2002, 27, 539-545, and references cited therein.
8. A. Bernardi, D. Potenza, A. M. Capelli, A. Garcia-Herrero, F. J. Cañada, J. Jiménez-Barbero, Chem. Eur. J. 2002, 8, 4597-4612.
9. A. Bernardi, D. Arosio, L. Manzoni, D. Monti, H. Posteri, D. Potenza, S. Mari, J. Jimenez-Barbero, Org. Biomol. Chem. 2003, 1, 785-792.
10. [9a] E. A. Merrit, S. Sarfaty, F. v. d. Akker, C. L'Hoir, J. A. Martial, W. G. J. Hol, Protein Sci. 1994, 3, 166-175.
11. [9b] E. A. Merrit, S. Sarfaty, M. G. Jobling, T. Chang, R. K. Holmes, T. R. Hirst, W. G. J. Hol, Protein Sci. 1997, 6, 1516-1528.
12. [9c] E. A. Merrit, W. G. J. Hol, Curr. Opin. Struct. Biol. 1995, 5, 165-171 and references cited therein.
13. [10a] D. Arosio, S. Baretti, S. Cattaldo, D. Potenza, A. Bernardi, Bioorg. Med. Chem. Lett. 2003, 13, 3831-3834.
14. [10b] A. Bernardi, D. Arosio, D. Potenza, I. Sanchez-Medina, S. Mari, F. J. Cañada, J. Jimenez-Barbero, Chem. Eur. J. 2004, 10, 4395-4406.
15. V. V. Samoshin, V. A. Chertkov, L. P. Vatlina, E. K. Dobretsova, N. A. Simonov, L. P. Kastorsky, D. E. Gremyachinsky, H.-J. Schneider, Tetrahedron Lett. 1996, 37, 3981-3984.
16. A. Bernardi, D. Arosio, D. Dellavecchia, F. Micheli, Tetrahedron: Asymmetry 1999, 40, 3403-3407.
17. [13a] T. Ren, D. Liu, Tetrahedron Lett. 1999, 40, 7621-7625.
18. [13b] R. R. Schmidt, J. Michel, Angew. Chem. Int. Ed. Engl. 1980, 19, 731-732.
19. [13c] R. R. Schmidt, Angew. Chem. Int. Ed. Engl. 1986, 25, 212-235.
20. W. Wang, F. Kong, J. Org. Chem. 1998, 63, 5744-5745; W. Wang, F. Kong, Angew. Chem. Int. Ed. 1999, 38, 1247-1250.
21. W. Wang, F. Kong, J. Org. Chem. 1998, 63, 5744-5745; W. Wang, F. Kong, Angew. Chem. Int. Ed. 1999, 38, 1247-1250.
22. R. J. Woods, A. Pathiaseril, M. R. Wormald, C. J. Edge, R. A. Dwek, Eur. J. Biochem. 1998, 259, 372-386, and references cited therein.
23. A. Bernardi, A. Colombo, I. Sánchez-Medina, Carbohydr. Res. 2004, 339, 967-973, and references cited therein.
24. M. R. Wormald, A. J. Petrescu, Y.-L. Pao, A. Glithero, T. Elliot, R. A. Dwek, Chem. Rev. 2002, 102, 371-386 and references cited therein.
25. Y.-T. Li, J. Biol. Chem. 1967, 242, 5474-5480.
26. [19a] Y. Bourne, V. Zamboni, A. Barre, W. J. Peumans, E. J. M. Van Damme, P. Rouge, Structure 1999, 7, 1473-1482.
27. [19b] D. N. Moothoo, B. Canan, R. A. Field, J. Naismith, Glycobiology 1999, 9, 539-545.
28. [19c] D. A. R. Sanders, D. N. Moothoo, J. Raftery, A. J. Howard, J. R. Helliwell, J. H. Naismith, J. Mol. Biol. 2001, 310, 875-884.
29. [19d] C. A. Bewley, Structure 2001, 9, 931-940; L. C. Chang, C. A. Bewley, J. Mol. Biol. 2002, 318, 1-8.
30. [19d] C. A. Bewley, Structure 2001, 9, 931-940; L. C. Chang, C. A. Bewley, J. Mol. Biol. 2002, 318, 1-8.
31. [19e] S. R. Shenoy, L. G. Barrientos, D. M. Ratner, B. R. O'Keefe, P. H. Seeberger, A. M. Gronenborn, M. R. Boyd, Chem. Biol. 2002, 9, 1109-1118.
32. [19f] C. A. Bewley, S. Kiyonaka, I. Hamachi, J. Mol. Biol. 2002, 322, 881-889.
33. [19g] C. N. Scanlan, R. Pantophlet, M. R. Wormald, E. O. Saphire, R. Stanfield, I. A. Wilson, H. Katinger, R. A. Dwek, P. M. Rudd, D. R. Burton, J. Virol. 2002, 76, 7306-7321.
34. W. B. Turnbull, B. L. Precious, S. W. Homans, J. Am. Chem. Soc. 2004, 126, 1047-1054.
35. F. Mohamadi, N. G. J. Richards, W. C. Guida, R. Liskamp, M. Lipton, C. Caufield, G. Chang, T. Hendrickson, W. C. Still, J. Comp. Chem. 1990, 11, 440-467.
36. H. Senderowitz, W. C. Still, J. Org. Chem. 1997, 62, 1427-1438.
37. W. C. Still, A. Tempzyk, R. Hawley, T. Hendrickson, J. Am. Chem. Soc. 1990, 112, 6127-6129.