Coumarin natural products are known to exhibit antimicrobial properties, and therefore have demonstrated potential in the synthesis of new antibiotics to combat antibiotic resistance. Peptoids are synthetic analogues of peptides, and may benefit in combating antibiotic resistance due to their similarity to known antimicrobial peptides. In combining coumarins with synthetic peptoids resistant to proteases, we hypothesize that the conjugate molecule will exhibit a similar level of antimicrobial activity to the coumarin with a potentially increased resilience to antibiotic resistance. This study aims to determine an effective synthesis pathway for two novel peptoid-coumarin conjugates, as well as analyze their chemical properties as potential antibiotics. Solid-state synthesis of peptoids using the sub-monomer method allowed us to couple carboxylic acid coumarins to the terminal nitrogen. Compounds were purified using reverse phase chromatography and characterized through HPLC, NMR and computational modelling. Future applications of our findings may entail combinatorial screening of the conjugates for antimicrobial activity as well as the development of an automated synthesis of the compounds.

Synthesis and characterization of coumarin-peptoid conjugates as potential antimicrobial compounds

ACS Spring Meeting 2021

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