Facile Synthesis of Biofunctional Oligosaccharides of Chondroitin Sulfate

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  • 生化学機能を持つコンドロイチン硫酸オリゴ糖の精密化学合成

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Abstract

<p>Chondroitin sulfate (CS) is present in many animal tissues with various sulfation patterns and is important in biological events. Mechanisms of interaction between CS and signal proteins have been widely investigated to allow the chemical synthesis of CS oligosaccharides. Sophisticated synthetic approaches adopting de novo synthesis starting from the corresponding monosaccharide have mainly been performed. This strategy usually employs stepwise glycan elongation, protecting group manipulation, and regio­specific sulfate formation to systematically obtain different types of bioactive CS oligosaccharides. On the other hand, the semi-synthetic method via optimized hydrolysis of CS polymer was performed for obtaining repeating disaccharide as an alternative strategy. The disaccharide unit obtained was again manipulated to form the desired CS oligosaccharides equipped with sulfates at specific positions. In addition, chemical re­construction including regiospecific sulfate formation of natural CS and CS-like polysaccharides has recently been explored. This review overviews the synthetic approaches to obtain biofunctional CS oligosaccharides emphasizing these aspects.</p>

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