Noah M. Bartfield, Tesia N. Stephenson, Timothy R. O’Leary, Mia L. Huang Proteoglycans are an important class of membrane-bound glycoconjugates consisting of glycosaminoglycan polysaccharides bound to serine or threonine residues along a core protein. Proteoglycans can regulate embryonic stem cell differentiation via growth factor recruitment to sulfated sites on glycosaminoglycans. The glycosaminoglycans themselves are comprised of repeating disaccharide units, and variations in these disaccharide units define the domain of activity. Synthetic small molecules derivatized from xylose monosaccharide can be used to re-direct glycosaminoglycan biosynthesis, and variations in the aglycone moiety of these structures have been shown to dramatically influence disaccharide sulfation patterns. To this end, the ambition of this project lies in the prospect of understanding how to utilize xyloside primers to accurately direct glycosaminoglycan biosynthesis and sulfation. In our investigation, we synthesized four xyloside types, each differing in either size of aglycone moieties, location of an azide functional handle on said moieties, or both. Synthetic primers were then incubated with human liver and Chinese hamster ovary cell lines with differing 2-O- and 6-O- sulfotransferase capabilities and fluorescence-based high-performance liquid chromatography was utilized to analyze the subsequent disaccharide sulfation patterns of extracted heparan sulfate glycosaminoglycans.

Investigating synthetic xyloside primers in directing sulfation of GAG-mimetic biololymers

Macromolecular Chemistry: The Second Century

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ACS Spring 2020 National Meeting & Expo

The official archive and repository for all ACS Meetings & Expositions abstracts and select posters or presentations.