Semi-synthesis of chondroitin sulfate-E from chondroitin sulfate-A |
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Authors: | Cai Chao Solakyildirim Kemal Yang Bo Beaudet Julie M Weyer Amanda Linhardt Robert J Zhang Fuming |
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Affiliation: | Department of Chemistry and Chemical Biology, Center for Biotechnology and Interdisciplinary Studies, Rensselaer Polytechnic Institute, Troy, New York 12180, USA. |
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Abstract: | Chondroitin sulfate-E (chondroitin-4, 6-disulfate) was prepared from chondroitin sulfate-A (chondroitin-4 - sulfate) by regioselective sulfonation, performed using trimethylamine sulfur trioxide in formamide under argon. The structure of semi-synthetic chondroitin sulfate-E was analyzed by PAGE, (1)H NMR, (13)C NMR, 2D NMR and disaccharide analysis and compared with natural chondroitin sulfate-E. Both semi-synthetic and natural chondroitin sulfate-E were each biotinylated and immobilized on BIAcore SA biochips and their interactions with fibroblast growth factors displayed very similar binding kinetics and binding affinities. The current semi-synthesis offers an economical approach for the preparation of the rare chondroitin sulfate-E from the readily available chondroitin sulfate-A. |
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