Synthesis and antimicrobial activity of binaphthyl-based, functionalized oxazole and thiazole peptidomimetics

Steven M Wales, Katherine A Hammer, Kittiya Somphol, Isabell Kemker, David C Schroder, Andrew J Tague, Zinka Brkic, Amy M King, Dena Lyras, Thomas V Riley, John B Bremner, Paul A Keller, Stephen G Pyne

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20 Citations (Scopus)


Thirty two new binaphthyl-based, functionalized oxazole and thiazole peptidomimetics and over thirty five novel leucine-containing intermediate oxazoles and thiazoles were prepared in this study. This includes the first examples of the direct C-5 arylation of an amino acid dipeptide-derived oxazole. Moderate to excellent antibacterial activity was observed for all new compounds across Gram positive isolates with MICs ranging from 1-16 mug mL(-1). Results for Gram negative E. coli and A. baumannii were more variable, but MICs as low as 4 mug mL(-1) were returned for two examples. Significantly, the in vitro results with a fluoromethyl-oxazole derivative collectively represent the best obtained to date for a member of our binaphthyl peptide antimicrobials.
Original languageEnglish
Pages (from-to)10813 - 10824
Number of pages12
JournalOrganic and Biomolecular Chemistry
Issue number44
Publication statusPublished - 2015

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