Peptide-Like Molecules (PLMs): A Journey from Peptide Bond Isosteres to Gramicidin S Mimetics and Mitochondrial Targeting Agents

Authors

  • Peter Wipf
  • Jingbo Xiao
  • Corey R. J. Stephenson

DOI:

https://doi.org/10.2533/chimia.2009.764

Keywords:

Alkene peptide bond isosteres, Cyclopropanes, Gramicidin s, Mitochondrial targeting, Organic synthesis

Abstract

Peptides are natural ligands and substrates for receptors and enzymes and exhibit broad physiological effects. However, their use as therapeutic agents often suffers from poor bioavailability and insufficient membrane permeability. The success of peptide mimicry hinges on the ability of bioisosteres, in particular peptide bond replacements, to adopt suitable secondary structures relevant to peptide strands and position functional groups in equivalent space. This perspective highlights past and ongoing studies in our group that involve new methods development as well as specific synthetic library preparations and applications in chemical biology, with the goal to enhance the use of alkene and cyclopropane peptide bond isosteres.

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Published

2009-11-27

Issue

Section

Scientific Articles

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