Synthetic carbohydrate receptors (SCRs) -- small molecules that bind cell-surface glycans -- could be used as sensors, delivery agents, and therapeutics, and could have a transformational impact on the glycosciences. We have developed a series of flexible tetrapodal SCRs composed of four heterocyclic binding moieties appended to a biaryl core that selectively bind the non-glucosidic carbohydrates that are prevalent on the surfaces of viruses and diseased cells. Here, we describe how the structures of these SCRs were varied systematically, and we present the profound affects of these changes on the affinity, selectivity, and stoichiometry of binding towards a series of biologically-relevant carbohydrates. These data have now led to a series of design rules for anticipating how the flexible SCRs change their structures in response to different glycans (<b>Figure</b>) and predicting how novel SCRs will bind different carbohydrates. Subsequently, we will present the potent activity against a series of flaviviruses and other diseases of pressing global concern.

Is rational design of selective synthetic carbohydrate receptors within reach? Implications on infectious disease

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.