Semi-synthesis of chondroitin sulfate-E from chondroitin sulfate-A

Cai, Chao
Solakyildirim, Kemal
Yang, Bo
Beaudet, Julie M.
Weyers, Amanda
Linhardt, Robert J.
Zhang, Fuming
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Biology , Chemistry and chemical biology , Chemical and biological engineering , Biomedical engineering
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Semi-synthesis of chondroitin sulfate-E from chondroitin sulfate-A, C. Cai, K. Solakyildirim, B. Yang, J. M. Beaudet, A. Weyers, R. J. Linhardt, F. Zhang, Carbohydrate Polymers, 87, 822-829, 2012.
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, 1H NMR, 13C 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.
Carbohydrate Polymers, 87, 822-829
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The Linhardt Research Labs.
The Shirley Ann Jackson, Ph.D. Center for Biotechnology and Interdisciplinary Studies (CBIS)
The Linhardt Research Labs Online Collection
Rensselaer Polytechnic Institute, Troy, NY
Carbohydrate Polymers
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