Introducing a C -interglycosidic bond in a biologically active pentasaccharide hardly affects its biological properties
| Autor: | Jean-Marc Herbert, Jean-Claude Lormeau, Maurice Petitou, Jean-Maurice Mallet, Pierre Sinaÿ, Arnim Helmboldt, Jean-Pascal Herault |
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| Rok vydání: | 1998 |
| Předmět: |
Magnetic Resonance Spectroscopy
Stereochemistry Antithrombin III Molecular Sequence Data Clinical Biochemistry Oligosaccharides Pharmaceutical Science Methylene bridge Biochemistry Structure-Activity Relationship chemistry.chemical_compound Biological property Drug Discovery Carbohydrate Conformation medicine Humans Glycosides Molecular Biology chemistry.chemical_classification Organic Chemistry Antithrombin Biological activity Heparin Oligosaccharide Oxygen atom Carbohydrate Sequence chemistry Molecular Medicine Factor Xa Inhibitors medicine.drug |
| Zdroj: | Bioorganic & Medicinal Chemistry. 6:1509-1516 |
| ISSN: | 0968-0896 |
| Popis: | We describe here the synthesis and the biological activity of a ‘C-pentasaccharide’, a new analogue of the antithrombin III (AT III) binding region of heparin containing a methylene bridge in place of an interglycosidic oxygen atom. The affinity for AT III and the anti-factor Xa activity of this compound have been compared with that of the corresponding selected ‘O-pentasaccharide’. Such a structural modification slightly decreased the affinity of this compound for AT III as well as its anti-factor Xa activity (880±40 anti-Xa units versus 1180±30 anti-Xa units for the C-pentasaccharide and the O-pentasaccharide, respectively). This compound therefore represents the first example of a new class of anti-factor Xa pentasaccharides containing a C-interglycosidic bond. |
| Databáze: | OpenAIRE |
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