Polymer-supported solution synthesis of heparan sulphate-like oligomers

Bioorganic and Medicinal Chemistry Letters

Volumn 7, Issue 9, 1997, Pages 1175-1180

  Dreef Tromp, C M ^a   Willems, H A M ^a   Westerduin, P ^a   Van Veelen, P ^a   Van Boeckel, C A A ^a  

^a NV ORGANON   (Netherlands)

Author keywords

[No Author keywords available]

Indexed keywords

HEPARAN SULFATE; OLIGOSACCHARIDE;

ARTICLE; CARBOHYDRATE SYNTHESIS; DRUG STRUCTURE; DRUG SYNTHESIS; IN VITRO STUDY; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; REACTION ANALYSIS; TECHNIQUE;

EID: 0030981661     PISSN: 0960894X     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0960-894X(97)00183-2     Document Type: Article

References (23)

1. Dreef - Tromp, C. M.; Willems, H. A. M.; Basten, J. E. M.; Westerduin, P.; van Boeckel, C. A. A. Abstracts, XVIIth International Carbohydrate Symposium 1994, 511.
2. Tina Au, Y. P.; Kenagy, R. D.; Clowes, M. M.; Clowes, A.W. Haemostasis 1993, 23, 177.
3. (a) Marcum, J. A.; Rosenberg, R. D. In Heparin; Lane, D. A., Lindahl, U, Eds; Edward Arnold: London, 1989, p. 275
4. (b) Mertens, G.; Cassiman, J. J.; van den Berghe, H.; Vermylen, J.; David, G. J. Biol. Chem. 1992, 267, 20435.
5. Guimond, R. D.; Maccarana, M.; Olwin, B. B.; Lindahl, U.; Rapraeger, A. C. J. Biol. Chem. 1993, 32, 23907.
6. Gallagher, J. T.; Turnbull, J. E. Glycobiology 1992, 6, 523.
7. (a) Petitou, M.; van Boeckel, C. A. A. In Progress in the Chemistry of Organic Natural Products, 1992, Vol 60, p 143
8. (b) van Boeckel, C. A. A.; Petitou, M. Angew. Chem. Ed. Engl. 1993, 32, 1671.
9. M. Petitou and coworkers prepared similar long HS-like fragments using solution-phase chemistry; personal communication.
10. Reviewed in: Krepinsky, J. J. In Modern Methods of Carbohydrate Synthesis Khan, S. H.; O'Neill, R. A., Eds; Harwood Academic Publishers. 1996
11. (b) Boons, G.-J. Tetrahedron 1996, 52, 1095.
12. Douglas, S. P.; Withfield, D. M.; Krepinsky, J. J. J. Am. Chem. Soc. 1991, 113, 5095.
13. Spijker, N. M.; Basten, J. E. M.; van Boeckel, C. A. A. Recl. Trav. Chim. Pays-Bas 1993, 112, 611.
14. Westerduin, P.; van Boeckel, C. A. A.; Basten, J. E. M.; Broekhoven, M. A.; Lucas, H.; Rood, A.; van der Heijden, H.; van Amsterdam, R.; van Dinther, T. G.; Meuleman, D. G.; Visser, A.; Vogel, G. M. T.; Damm, J. B. L.; Overklift, G. T. Bioorg. Med. Chem. Lett. 1994, 2, 1267.
15. Antonsen, K. P.; Hoffman, A. S. In Poly(ethylene glycol) Chemistry Milton Hams, J., Eds. 1992, 17.
16. Capping was only implemented in the elongation cycle if heterogenic sequences were prepared.
17. Evans, D. Tetrahedron Lett. 1987, 25, 6141.
18. The sulphated oligosaccharides IV-VII contain small amounts of oligosaccharides of which the terminal non-reducing sugar unit is a δ-4,5 uronic acid derivative. These impurities are formed during the sulphation via β-elimination and unfortunately were not separable from the final compounds.
19. van Veelen, P. et al. to be published.
20. Damm, J. B. L.; Overklift, G. T.; Vermeulen, B. W. M.; Fluitsma, C. F.; van Dedem, G. W. K. J. Chromotography 1992, 608, 297.
21. (a) Juhasz, P.; Biemann, K. Proc. Natl. Acad. Sci. U.S.A. 1994, 4333
22. (b) Juhasz, P.; Biemann, K. Carbohydrate Res. 1995, 270, 131.
23. A fully protected pegylated hexasaccharide with a heterogenic structure prepared via PEG-supported solution synthesis using disaccharide synthons is illustrated below.