Chemical Synthesis of Modified Hyaluronic Acid Disaccharides.

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, H NMR studies of the new derivatives demonstrated the effect of the various functional groups on the intramolecular electronic environment.