Glycosidated ellagic acid derivatives have demonstrated antibacterial and antibiofilm properties against a variety of infectious pathogens. The nature of glycosidation critically impacts biological activity, but the mechanisms behind this remain poorly understood. We have utilized a total synthesis of ellagic acid featuring a sterically-encumbered Ullmann coupling. From this route, we have made three unique mono-glycosidated ellagic acid derivatives that demonstrate broad antibacterial activity against a variety of ESKAPE pathogens. Additionally, the compounds exhibit interesting antibacterial and antibiofilm properties in Streptococcus agalactiae andmethicillin-resistant Staphylococcus aureus. These initial findings showcase the impact of glycan identity on biological activity and pave the way for continued mechanistic studies.

Synthesis and biological evaluation of ellagic acid glycosides

2019 Fall National Meeting

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