Synthesis of New Regioselectively Sulfated Hyaluronans for Biomedical Application |
| |
Authors: | Jana Becher Stephanie Möller Dieter Weiss Jürgen Schiller Matthias Schnabelrauch |
| |
Affiliation: | 1. INNOVENT e.V., Department of Biomaterials, Prüssingstr. 27B, D-07745 Jena, Germany;2. Friedrich-Schiller-University Jena, Institute of Organic and Macromolecular Chemistry, Humboldtstrasse 10, D-07743 Jena, Germany;3. University of Leipzig, Institute of Medical Physics and Biophysics, Härtelstraße 16-18, D-04107 Leipzig, Germany |
| |
Abstract: | Sulfated glycosaminoglycans (GAGs) display various biological effects which are strongly influenced by the degree of sulfation and the position of sulfate groups within the polymer. Hyaluronan, a non-sulfated GAG, represents a readily accessible educt to synthesize structural analogues of sulfated GAGs mimicking their biological activity. Different strategies were developed and evaluated to synthesize hyaluronan sulfates with a free primary hydroxyl group at C-6' and sulfated secondary hydroxyl groups. Applying selective desulfation methods of high-sulfated hyaluronan by means of silylating agents, products regioselectively desulfated at the primary C-6' but also partly the C-4' position were obtained. A pathway using benzoyl ester protecting groups to block the primary hydroxyl function of Hya during the sulfation resulted in a high-sulfated product, functionalized only at the secondary hydroxyl groups. |
| |
Keywords: | biomaterials esterification hyaluronan regioselective sulfation |
|
|