Chemoenzymatic iterative synthesis of difficult linkages of oligosaccharides on soluble polymeric supports

Organic Letters

Volumn 3, Issue 21, 2001, Pages 3265-3268

  Yan, Fengyang ^a   Gilbert, Michel ^a   Wakarchuk, Warren W ^a   Brisson, Jean Robert ^a   Whitfield, Dennis M ^a  

^a NATIONAL RESEARCH COUNCIL CANADA   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

GLYCOSYLTRANSFERASE; MACROGOL DERIVATIVE; MONOMETHOXYPOLYETHYLENE GLYCOL; OLIGOSACCHARIDE; TRISACCHARIDE; VEROTOXIN 1;

ARTICLE; CHEMISTRY; CONFORMATION; GLYCOSYLATION; METABOLISM; NUCLEAR MAGNETIC RESONANCE; PROTEIN BINDING; SYNTHESIS;

CARBOHYDRATE CONFORMATION; GLYCOSYLATION; GLYCOSYLTRANSFERASES; NUCLEAR MAGNETIC RESONANCE, BIOMOLECULAR; OLIGOSACCHARIDES; POLYETHYLENE GLYCOLS; PROTEIN BINDING; SHIGA-LIKE TOXIN I; TRISACCHARIDES;

EID: 0035909644     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol016466j     Document Type: Article

References (28)

1. (a) Belogi, G.; Zhu, T.; Boons, G.-J. Tetrahedron Lett. 2000, 41, 6969.
2. (b) Flitsch, S. L.; Watt, G. M. Glycopeptides and Related Compounds; Large, D. G., Warren, C. D., Ed.; Marcel Dekker: New York, 1997; p 207.
3. (a) Endo, T.; Koizumi, S. Curr. Opin. Struct. Biol. 2000, 10, 536.
4. (b) Windmuller, R.; Schmidt, R. R. Tetrahedron Lett. 1994, 35, 7927.
5. (a) Krepinsky, J. J.; Douglas, S. P. Carbohydrates in Chemistry and Biology, Part I: Chemistry of Saccharides; Ernst, B., Hart, G. W., Sinay, P., Ed.; Wiley-VCH: Weinheim, 2000.
6. (b) Haase, W.-C; Seeberger, P. H. Curr. Org. Chem. 2000, 4, 481.
7. Douglas, S. P.; Whitfield, D. M.; Krepinsky, J. J. J. Am. Chem. Soc. 1995, 117, 2116.
8. (a) Kitov, P. I.; Sadowska, J. M.; Mulvey, G.; Armstrong, G. D.; Ling, H.; Pannu, N. S.; Read, R. J.; Bundle, D. R. Nature 2000, 403, 669.
9. (b) Fan, E.; Merritt, E. A.; Verlinde, C. L. M. J.; Hol, W. G. J. Curr. Opin. Struct. Biol. 2000, 10, 680.
10. Nukada, T.; Berces, A.; Whitfield, D. M. J. Org. Chem. 1999, 64, 9030.
11. Wakarchuk, W. W.; Cunningham, A.; Watson D. C.; Young, N. M. Protein Eng. 1998, 11, 295.
12. C).
13. +).
14. Mehta, S.; Gilbert, M.; Wakarchuk, W. W.; Whitfield, D. M. Org. Lett. 2000, 2, 751.
15. Zhu, T.; Boons, G.-J. J. Am. Chem. Soc. 2000, 122, 10222.
16. (a) Wakarchuk, W. W.; Martin, A.; Jennings, M. P.; Moxon, E. R.; Richards, J. C. J. Biol. Chem. 1996, 271, 19166.
17. (b) α(2→3)Sialyltransferases from C. jejuni: Gilbert, M., Brisson, J.-R.; Karwaski, M.-F.; Michniewicz, J.; Cunningham, A.-M.; Wu, Y.; Young, N. M.; Wakarchuk, W. W. J. Biol. Chem. 2000, 275, 3896.
18. Blanken, W. M.; Van den Eijnden, D. H. J. Biol. Chem. 1985, 260, 12927.
19. (a) Fang, J.; Li, J.; Chen, X.; Zhang, X.; Wang, J.; Guo, Z.; Zhang, W.; Yu, L.; Brew, K.; Wang, P. G. J. Am. Chem. Soc. 1998, 120, 6635.
20. (b) Hanessian, S.; Saavedra, O. M.; Mascitti, V.; Marterer, W.; Oehrlein, R.; Mak, C.-P. Tetrahedron 2001, 57, 3267.
21. Schmidt, D.; Thiem, J. J. Chem. Soc, Chem. Commun. 2000, 1919.
22. Lubineau, A.; Malleron, A.; Le Narvor, C. Tetrahedron Lett. 2000, 41, 8887.
23. FCHASE is a fluorescein derivative; see: Gilbert, M.; Cunningham, A.-M.; Watson, D. C.; Martin, A.; Richards, J. C.; Wakarchuk, W. W. Eur. J. Biochem. 1997, 249, 187.
24. Clark, C.; Bast, D.; Sharp, A. M.; St. Hilaire, P.; Agha, R.; Stein, P. E.; Toone, E. J.; Read, R. J.; Brunton, J. L. Mol. Microbiol. 1996, 19, 891.
25. (a) Shimizu, H.; Field, R. A.; Homans, S. W.; Donohue-Rolfe, A. Biochemistry 1998, 37, 11078.
26. (b) Thompson, G. S.; Shimizu, H.; Homans, S. W.; Donohue-Rolfe, A. Biochemistry 2000, 39, 13153.
27. (c) Ling, H.; Boodhoo, A.; Hazes, B.; Cummings, M. D.; Armstrong, G. D.; Brunton, J. L.; Read, R. J. Biochemistry 1998, 37, 1777.
28. Van, F. Y.; Wakarchuk, W. W.; Gilbert, M.; Richards, J. C.; Whitfield, D. M. Carbohydr. Res. 2000, 328, 3.