Efficient and Stereocontrolled Construction of Homo‐ and Heterogeneously 4‐ and 6‐Sulfated Biotinylated Chondroitin Oligomers

Abstract

An efficient and stereocontrolled construction of homo‐ and heterogeneously 4‐ and 6‐sulfated biotinylated chondroitin oligomers has been investigated and is reported for the first time. This procedure allowed the preparation of oligomeric chondroitin derivatives with sulfate groups at specific positions; these should be useful probes for the study of the starting point of the polymerization reaction as well as the substrate specificity of sulfotransferases involved in the biosynthesis of chondroitin sulfate chains.

From Chondroitin Polymer to Size‐Defined Hyaluronan Oligosaccharides

“…It must be emphasized that we were also able to obtain the target disaccharide 2 from the known compound 16 (obtained in nine steps from 1 12c) by inversion of configuration at C‐4 followed by benzoylation (Scheme ).…”

Chondroitin sulfate: extraction, purification, microbial and chemical synthesis

“…Synthesis of homogeneously and heterogeneously 4‐ and 6‐sulfated biotinylated tri‐ and tetrasaccharides …”

“…In 2011, the same author and co-workers reported stereocontrolled construction of homo and heterogeneously 4and 6-sulfated biotinylated chondroitin oligomers (from di-to tetrasaccharide). 113 The disaccharide collection ( Fig. 14) was prepared from the known derivative 95, which upon benzylidene hydrolysis gave a diol.…”

“…Synthesis of homogeneously and heterogeneously 4-and 6-sulfated biotinylated tri-and tetrasaccharides. 113 For the extraction technique, the main research is to improve current extraction techniques and determine a new simple and practical process to reduce the amount of extraction solvent, and to improve extraction efficiency, as well as to ensure high quality products. With respect to the aspect of separation and purification techniques, there are a lot of essential efforts devoted to refining the species of ChS and improving the purity of ChS and apply the new techniques obtained from the lab into industrial production.…”

“…Synthesis of biotinylated nonsulfated chondroitin oligosaccharides (from di-to octasaccharide) 113. by the semi-synthesis described by Jacquinet et al in 2006.…”