As part of a program investigating cyclic peptides with an internal aromatic hydrophobic scaffold as potential novel anti-bacterial agents, we explored the synthesis of simple tyrosine-based systems. These were prepared via key intermediates containing internal allylglycine and allyltyrosine residues for subsequent ring closing metathesis reactions. Although the resulting anti-bacterial activity against Staphylococcus aureus was modest, this represents a novel and simple route to this class of compounds. One intermediate acyclic dipeptide precursor showed good activity against S. aureus with an MIC of 7.8 µg/mL.
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This article was originally published as Boyle, TP, Bremner, JB, Coates, J, Deadman, J, Keller, PA, Pyne, SG & Rhodes, DI, New Cyclic Peptides via Ring-Closing Metathesis Reactions and Their Anti-Bacterial Activities, Tetrahedron, 64(49), 2008, 11270-11290. Original journal article available here