Design and synthesis of macrocyclic peptomers as mimics of a quorum sensing signal from Staphylococcus aureus.
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.
Fowler
Sarah A
SA
Department of Chemistry, University of Wisconsin-Madison, Madison, WI 53706-1322, USA.
Stacy
Danielle M
DM
Blackwell
Helen E
HE
D001426:Bacterial Proteins / Q000138:chemical synthesis* / Q000737:chemistry; D008958:Models, Molecular; D018716:Molecular Mimicry; D019151:Peptide Library; D010456:Peptides, Cyclic / Q000737:chemistry*; D053038:Quorum Sensing; D013211:Staphylococcus aureus / Q000737:chemistry*
C414532:AgrD protein, Staphylococcus; D001426:Bacterial Proteins; D019151:Peptide Library; D010456:Peptides, Cyclic