3 years ago

Chemical Synthesis of Modified Hyaluronic Acid Disaccharides

Chemical Synthesis of Modified Hyaluronic Acid Disaccharides
Martin Nieger, Stefan Bräse, Marco Mende
Herein we report a chemical synthesis towards new modified hyaluronic acid oligomers by using only commercially available d-glucose and d-glucosamine hydrochloride. The various protected hyaluronic acid disaccharides were synthesized bearing new functional groups at C-6 of the β-d-glucuronic acid moiety with a view to structure-related biological activity tests. The orthogonal protecting group pattern allows ready access to the corresponding higher oligomers. Also, 1H NMR studies of the new derivatives demonstrated the effect of the various functional groups on the intramolecular electronic environment. Functional disaccharides: Various novel hyaluronic acid disaccharide derivatives with a distinct protecting group pattern that allows easy access to higher oligomers have been synthesized (see figure). 1H NMR studies demonstrated changes in the electronic environment within the molecules, especially at the hydrogen-bonding amide proton, that could result in new properties or biological activities of the corresponding higher oligomers.

Publisher URL: http://onlinelibrary.wiley.com/resolve/doi

DOI: 10.1002/chem.201701238

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