First Synthetic Carbohydrates with the Full Anticoagulant Properties of Heparin

Maurice Petitou; Philippe Duchaussoy; Pierre-A Driguez; Guy Jaurand; Jean-P Hérault; Jean-C Lormeau; Constant A A van Boeckel; Jean-M Herbert

doi:10.1002/(SICI)1521-3773(19981116)37:21<3009::AID-ANIE3009>3.0.CO;2-F

First Synthetic Carbohydrates with the Full Anticoagulant Properties of Heparin

Angew Chem Int Ed Engl. 1998 Nov 16;37(21):3009-3014. doi: 10.1002/(SICI)1521-3773(19981116)37:21<3009::AID-ANIE3009>3.0.CO;2-F.

Authors

Maurice Petitou¹, Philippe Duchaussoy¹, Pierre-A Driguez¹, Guy Jaurand¹, Jean-P Hérault¹, Jean-C Lormeau¹, Constant A A van Boeckel², Jean-M Herbert¹

Affiliations

¹ Sanofi Recherche, Haemobiology Research Department, 195, route d'Espagne, F-31036 Toulouse Cedex (France), Fax: (+33) 5-61-16-22-86.
² N.V. Organon, Oss (The Netherlands).

Abstract

A single disaccharide building block is required to obtain synthetic carbohydrates that reproduce the anticoagulant activity of heparin and inhibit thrombin (n>6) and/or factor Xa (n≥2; see reaction scheme). Thus, there is evidence that heparin fragments with at least 15 saccharide units are required for thrombin inhibition. Lev=levulinoyl.

Keywords: Drug research; Enzyme inhibitors; Heparin; Oligosaccharides; Serine proteinases.