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Design and Synthesis of Macrocyclic Peptomers as Mimics of a Quorum Sensing Signal from Staphylococcus aureus

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journal contribution
posted on 19.06.2008 by Sarah A. Fowler, Danielle M. Stacy, Helen E. Blackwell
We report the design and synthesis of macrocyclic peptide-peptoid hybrids (peptomers) as analogs of autoinducing peptide I (AIP-I) from Staphylococcus aureus. Our solid-phase synthetic route includes efficient microwave-assisted reactions and a tandem macrocyclization-cleavage step, and we demonstrate its compatibility with parallel synthesis through the generation of a focused peptomer library. One of the peptomers was capable of stimulating biofilm formation in S. aureus, a phenotype linked to AIP-I receptor (AgrC-I) inhibition.