Solvolytic depolymerization of chondroitin and dermatan sulfates |
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Authors: | Toshihiko Toida Kenji Sato Shinobu Sakai Saori Hosoyama |
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Institution: | a Graduate School of Pharmaceutical Sciences, Chiba University, 263-8522 Chiba, Japan b Department of Chemistry and Chemical Biology, Biology and Chemical and Biological Engineering, Rensselaer Polytechnic Institute, Troy, NY 12180, USA |
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Abstract: | It is essential to establish a library of glycosaminoglycan oligosaccharides from the chondroitin and dermatan sulfates to investigate their biological functions and structure-activity relationships (SARs). There are several approaches to obtain oligosaccharides using chemical and enzymatic degradation procedures; however, purification of each resulting oligosaccharide is complicated because of the diversity of sulfonation patterns present in these oligosaccharides. We have developed a new method for the solvolytic degradation for chondroitin and dermatan sulfates to obtain an oligosaccharide mixture that can be easily purified into chondro/dermato oligosaccharides for characterization by both 1H NMR and MALDI-TOFMS. These oligosaccharides have a methyl-esterified uronate residue and a methyl 2-acetamido-2-deoxy-d-galactofuranoside at the nonreducing and reducing ends, respectively. All other internal repeating disaccharide units were desulfonated, but maintained their core carbohydrate structures. |
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Keywords: | Chondroitin sulfate Dermatan sulfate Oligosaccharide depolymerization Solvolysis Sulfonation |
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