Investigation of the stability of thiosialosides toward hydrolysis by sialidases using NMR spectroscopy

Organic Letters

Volumn 1, Issue 3, 1999, Pages 443-446

  Wilson, Jennifer C ^a   Kiefel, Milton J ^a   Angus, Donald I ^a   Von Itzstein, Mark ^a  

^a MONASH UNIVERSITY   (Australia)

Author keywords

[No Author keywords available]

Indexed keywords

SIALIC ACID DERIVATIVE; SIALIDASE;

ARTICLE; CARBOHYDRATE ANALYSIS; CHEMISTRY; CONFORMATION; HYDROLYSIS; MOLECULAR GENETICS; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; VIBRIO CHOLERAE;

CARBOHYDRATE SEQUENCE; HYDROLYSIS; MAGNETIC RESONANCE SPECTROSCOPY; MOLECULAR CONFORMATION; MOLECULAR SEQUENCE DATA; NEURAMINIDASE; SIALIC ACIDS; VIBRIO CHOLERAE;

EID: 0033549661     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol990652w     Document Type: Article

References (38)

1. For reviews see: (a) Schauer, R.; Kamerling, J. P. Glycoproteins II; Montreuil, J., Vliegenthart, J. F. G., Schachter, H., Eds.; Elsevier: Amsterdam, 1997; pp 243-402.
2. (b) Saito, M.; Yu, R. K. Biology of the Sialic Acids; Rosenberg, A., Ed.; Plenum Press: New York, 1995; pp 261-313.
3. (c) Traving, C.; Schauer, R. Cell. Mol. Life Sci. 1998, 54, 1330-1349.
4. Taylor, G. Curr. Opin. Struct. Biol. 1996, 6, 830-837.
5. Driguez, H. Top. Curr. Chem. 1997, 187, 85-116.
6. Hasegawa, A.; Kiso, M. Carbohydrates: Synthetic Methods and Applications in Medicinal Chemistry; Ogura, H., Hasegawa, A., Suami, T., Eds.; VCH: New York, 1992; pp 243-266.
7. Suzuki, Y.; Sato, K.; Kiso, M.; Hasegawa, A. Glycoconjugate J. 1990, 7, 349-356.
8. (a) Warner, T. G.; Lee, L. A. Carbohydr. Res. 1988, 176, 211-218.
9. (b) Roy, R. Carbohydrates in Drug Design; Witczak, Z. J., Nieforth, K. A., Eds.; Marcel Dekker: New York, 1997; pp 83-135.
10. (c) von Itzstein, M.; Kiefel, M. J. Carbohydrates in Drug Design; Witczak, Z. J., Nieforth, K. A., Eds.; Marcel Dekker: New York, 1997; pp 39-82.
11. (d) Zanini, D.; Roy, R. J. Org. Chem. 1998, 63, 3486-3491.
12. (e) Park, W. K. C.; Meunier, S. J.; Zanini, D.; Roy, R. Carbohydr. Lett. 1995, 1, 179-184.
13. (f) Eisele, T.; Schmidt, R. R. Liebigs Ann. 1997, 865-872.
14. (g) Eisele, T.; Toepfer, A.; Kretzschmar, G.; Schmidt, R. R. Tetrahedron Lett. 1996, 37, 1389-1392.
15. Bennett, S.; von Itzstein, M.; Kiefel, M. J. Carbohydr. Res. 1994, 259, 293-299.
16. Kiefel, M. J.; Beisner, B.; Bennett, S.; Holmes, I. D.; von Itzstein, M. J. Med. Chem. 1996, 39, 1314-1320.
17. (a) Angus, D. I.; von Itzstein, M. Carbohydr. Res. 1995, 274, 279-283.
18. (b) Ciccotosto, S.; Kiefel, M. J.; Abo, S.; Stewart, W.; Quelch, K.; von Itzstein, M. Glycoconjugate J. 1998, 15, 663-669.
19. (c) Smalec, B.; von Itzstein, M. Carbohydr. Res. 1995, 266, 269-272.
20. Khorlin, A. Y.; Privalova, I. M.; Zakstelskaya, L. Y.; Molibog, E. V.; Evstigneeva, N. A. FEBS Lett. 1970, 8, 17-19.
21. Privalova, I. M.; Khorlin, A. Y. Izv. Akad. Nauk SSSR 1969, 12, 2785-2792; Chem. Abstr. 1970, 72, 90785y.
22. Privalova, I. M.; Khorlin, A. Y. Izv. Akad. Nauk SSSR 1969, 12, 2785-2792; Chem. Abstr. 1970, 72, 90785y.
23. Sabesan, S.; Neira, S.; Davidson, F.; Duus, J. Ø.; Bock, K. J. Am. Chem. Soc. 1994, 116, 1616-1634.
24. 4.3 3.0 Hz, GalH-4), 3.95 (1H, dd, GalH-3), 4.25 (1H, d, GalH-1).
25. 3N), filtered, concentrated, and then chromatographed.
26. Martin, T. J.; Brescello, R.; Toepfer, A.; Schmidt, R. R. Glycoconjugate J. 1993, 10, 16-25.
27. Vliegenthart, J. F. G.; Dorland, L.; van Halbeek, H.; Haverkamp, J. In Sialic Acids: Chemistry Metabolism and Function; Schauer, R., Ed.; Cell Biology Monographs; Springer-Verlag: Wein, 1982; Vol. 10, pp 127-171.
28. 2O prior to the addition of enzyme (representing time = 0 s). After addition of enzyme, spectra of 32 scans were acquired frequently over the first hour of incubation (e.g., every 5-10 min) and then less frequently for several hours longer (approximately every 15 min), with 16K data points over a spectral width of 6024 Hz and a relaxation delay of 2 s.
29. (a) Wilson, J. C.; Angus, D. I.; von Itzstein, M. J. Am. Chem. Soc. 1995, 117, 4214-4217.
30. (b) Wilson, J. C.; Kong, D. C. M.; Li, Y.-T.; von Itzstein, M. Glycoconjugate J. 1996, 13, 927-931.
31. Chong, A. K. J.; Pegg, M. S.; Taylor, N. R.; von Itzstein, M. Eur. J. Biochem. 1992, 207, 335-343.
32. 1,2 6.6 Hz, GalH-1).
33. Full details of the synthesis of compound 9, and related compounds, will be published in due course.
34. 1H NMR spectra were acquired after 8 h, 14 days, and 70 days of incubation with enzyme.
35. For related discussions see: (a) Defaye, J.; Gelas, J. Studies in Natural Products Chemistry; Atta-ur-Rahman, Ed.; Elsevier: Amsterdam, 1991; Vol. 8, pp 315-357.
36. (b) Sulzenbacher, G.; Driguez, H.; Henrissat, B.; Schülein, M.; Davies, G. J. Biochemistry 1996, 35, 15280-15287.
37. (c) Horton, D.; Hutson, D. H. Adv. Carbohydr. Chem. 1963, 18, 123-129.
38. Groves, D. R.; Bradley, S. J.; Rose, F. J.; Kiefel, M. J.; von Itzstein, M. Glycoconjugate J. 1999, in press.