Glycosaminoglycans (GAGs) are among the most complex, biologically active biopolymers in nature. The complexity of GAGs greatly impedes their synthesis, thus complicating the structure-property understanding. We design a regiospecific synthetic route to two types of GAG analogs by chemical modification of commercially available, inexpensive cellulose acetate. Cellulose acetate was first brominated, followed by azide displacement to introduce azides. The resulting 6-N<sub>3</sub> cellulose acetate was then saponified to liberate 6-OH groups. Subsequent oxidation of the liberated primary hydroxyl groups to carboxyl groups was smoothly effected by a TEMPO-catalyzed process. Finally, the azides were reduced to amines using an aqueous process, new to polysaccharide chemistry, employing reduction by dithiothreitol (DTT). Alternatively, another process new to polysaccharide chemistry could be employed to convert most of the azides to acetamido groups by reduction with thioacetic acid. In summary, we successfully prepare two GAG analogs, which provides access to GAG analogs that will be of great interest for exploring structure-property relationships in various biomedical applications.

Efficient synthesis of novel glycosaminoglycan analogs

2019 Spring National Meeting

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