INTRODUCING A C-INTERGLYCOSIDIC BOND IN A BIOLOGICALLY-ACTIVE PENTASACCHARIDE HARDLY AFFECTS ITS BIOLOGICAL PROPERTIES

We describe here the synthesis and the biological activity of a 'C-pen tasaccharide', a new analogue of the antithrombin III (AT III) binding region of heparin containing a methylene bridge in place of an interg lycosidic oxygen atom. The affinity for AT III and the anti-factor Xa activity of this compound have been compared with that of the correspo nding selected 'O-pentasaccharide'. Such a structural modification sli ghtly decreased the affinity of this compound for AT III as well as it s anti-factor Xa activity (880 +/- 40 anti-Xa units versus 1180 +/- 30 anti-Xa units for the C-pentasaccharide and the O-pentasaccharide, re spectively). This compound therefore represents the first example of a new class of anti-factor Xa pentasaccharides containing a C-interglyc osidic bond. (C) 1998 Published by Elsevier Science Ltd. All rights re served.