Glycans coat bacterial cells and are intriguing therapeutic targets due to their observed role in pathogenesis and their species-dependent expression. However, because there are over 700 monosaccharides found in bacterial glycans, the complexity of these structures makes them difficult to study by conventional methods. Here, we developed fluorescent analogs of the bacterial monosaccharides D-di-N-acetylbacillosamine, D-N-acetylfucosamine (FucNAc), and D-2,4-diacetamido-2,4,6-trideoxygalactose (DATDG) to probe bacterial monosaccharide uptake and glycan degradation. We assessed uptake of NBD sugars across bacterial pathogens, including Helicobacter pylori and Campylobacter jejuni, and symbiotic gut bacteria. Further, we developed fluorogenic glycosides based on the rare bacterial sugars bacillosamine, FucNAc, and DATDG and assessed their activation by glycosylhydrolases present in bacterial and mammalian cells and lysates. We will present our latest results with these novel probes based on bacterial monosaccharide scaffolds. This new suite of probes will provide a tool for the bacterial glycoscience community to address unknowns regarding monosaccharide uptake and glycosylhydrolase activity, ultimately paving the way for selective and effective glycan-based bacterial diagnostics and therapeutics.

Using fluorescent chemical probes to study glycosylation pathways in bacteria

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