Preparation and anticoagulant activity of fully O-sulphonated glycosaminoglycans

Toshihiko Toida, Tomohiro Maruyama, Yoshiaki Ogita, Atsushi Suzuki, Hidenao Toyoda, Toshio Imanari, Robert J. Linhardt

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Glycosaminoglycans including dermatan sulphate, hyaluronan, heparan sulphate and heparin were chemically modified by O-sulphonation. By altering the reaction conditions, products having a different degree of O-sulphonation could be obtained. Glycosaminoglycan derivatives were prepared having no free hydroxyl groups, with sulphoester group/disaccharide unit ratios of 4.0 for dermatan sulphate and hyaluronan, and sulphoester and sulphamide group/disaccharide unit ratios of 4.22 and 4.88 for heparan sulphate and heparin, respectively. 1H NMR spectroscopy showed that the fully O-sulphonated hyaluronan derivative had a glucuronate residue with an altered conformation. Since glycosaminiglycans and their derivatives are often used as anticoagulant/antithrombotic agents, their anti-amidolytic activities were determined. The anti-factor IIa activity of fully O-sulphonated dermatan sulphate, hyaluronan and heparan sulphate ranged from 40 to 80 units/mg, while no anti-factor Xa activity of the fully O-sulphonated glycosaminoglycans was detected. These values are lower than those reported for low-molecular-weight heparins and are consistent with the requirement of an antithrombin III pentasaccharide binding site for anti-factor Xa activity. Interestingly, the anti-factor Xa of heparin is lost by chemical O-sulphonation. Copyright (C) 1999 Elsevier Science B.V.

Original languageEnglish
Pages (from-to)233-241
Number of pages9
JournalInternational Journal of Biological Macromolecules
Issue number4
StatePublished - 1 Dec 1999
Externally publishedYes


  • Anticoagulant activity
  • Chemical oversulphonation
  • Glycosaminoglycan


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