A new, highly potent, heparin-like pentasaccharide fragment containing a glucose residue instead of a glucosamine

The synthesis is reported of a new heparin-like pentasaccharide fragment in which the reducing end glucosamine unit is replaced by a glucose residue. This indicates that an O-sulfate can be substituted for a N-sulfate thereby allowing simpler synthesis of this kind of compounds. A new route using a...

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Bibliographic Details
Published in:Bioorganic & medicinal chemistry letters 1991, Vol.1 (2), p.95-98
Main Authors: Petitou, M., Jaurand, G., Derrien, M., Duchaussoy, P., Choay, J.
Format: Article
Language:English
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Summary:The synthesis is reported of a new heparin-like pentasaccharide fragment in which the reducing end glucosamine unit is replaced by a glucose residue. This indicates that an O-sulfate can be substituted for a N-sulfate thereby allowing simpler synthesis of this kind of compounds. A new route using a trisaccharide imidate as glycosyl donor was developed for this preparation. The synthesis of a heparin-like pentasaccharide containing a glucose residue at the reducing end was achieved using a new synthetic route. The product displays high biological activity.
ISSN:0960-894X
1464-3405
DOI:10.1016/S0960-894X(00)80238-3