Dextran thioparaconate – Evaluation of the multifunctional thiolactone linker for easily adaptable polysaccharide modification

Abstract

For the preparation of tailored polymers based on polysaccharides, an easy adaptable modification method was developed by introduction of a multifunctional linker into the polymer backbone. Dextran was functionalized with a thiolactone compound that can be further treated with amine resulting in ring opening and formation of a thiol. The functional thiol group emerging can be used for crosslinking or introduction of a further functional compound by disulfide formation. Here, the efficient esterification of thioparaconic acid after in-situ activation and studies about reactivity of the dextran thioparaconate obtained are discussed. The derivative was converted by aminolysis with model compound hexylamin and the thiol generated therefrom was subsequently converted with an activated functional thiol to the corresponding disulfide. The thiolactone, which protects the thiol, enables efficient esterification without side reactions and allows storage of the polysaccharide derivative at ambient conditions for years. Not only the multifunctional reactivity of the derivative but also the end product with a balanced ratio of hydrophobic and cationic moiety is appealing for biomedical application.