Premium
Chemical Synthesis of Modified Hyaluronic Acid Disaccharides
Author(s) -
Mende Marco,
Nieger Martin,
Bräse Stefan
Publication year - 2017
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201701238
Subject(s) - hyaluronic acid , moiety , chemistry , glucuronic acid , intramolecular force , glucosamine , chemical structure , hydrochloride , chemical modification , organic chemistry , combinatorial chemistry , polysaccharide , biochemistry , genetics , biology
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, 1 H NMR studies of the new derivatives demonstrated the effect of the various functional groups on the intramolecular electronic environment.