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Life Sciences Commons

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Selected Works

2010

Physical Sciences and Mathematics

Paul Keller

Cyclic peptoid

Articles 1 - 2 of 2

Full-Text Articles in Life Sciences

Synthesis Of Some Cyclic Indolic Peptoids As Potential Antibacterials, Vicki S. Au, John B. Bremner, Jonathan Coates, Paul A. Keller, Stephen G. Pyne Aug 2010

Synthesis Of Some Cyclic Indolic Peptoids As Potential Antibacterials, Vicki S. Au, John B. Bremner, Jonathan Coates, Paul A. Keller, Stephen G. Pyne

Paul Keller

The synthesis of cyclic peptoids containing an indole hydrophobic scaffold has been realised through the ring-closing metathesis of diallylated precursors. The precursors and their cyclic counterparts possessed poor antibacterial activity in contrast to previously reported cyclic peptoids containing hydrophobic scaffolds.


New Cyclic Peptides Via Ring-Closing Metathesis Reactions And Their Anti-Bacterial Activities, Timothy P. Boyle, John B. Bremner, Jonathan Coates, John Deadman, Paul A. Keller, Stephen G. Pyne, David I. Rhodes Aug 2010

New Cyclic Peptides Via Ring-Closing Metathesis Reactions And Their Anti-Bacterial Activities, Timothy P. Boyle, John B. Bremner, Jonathan Coates, John Deadman, Paul A. Keller, Stephen G. Pyne, David I. Rhodes

Paul Keller

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.