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Peptide-Like Molecules (PLMs): A journey from peptide bond isosteres to gramicidin s mimetics and mitochondrial targeting agents

Wipf, P and Xiao, J and Stephenson, CRJ (2009) Peptide-Like Molecules (PLMs): A journey from peptide bond isosteres to gramicidin s mimetics and mitochondrial targeting agents. Chimia, 63 (11). 764 - 775. ISSN 0009-4293

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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. © Schweizerische Chemische Gesellschaft.


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Details

Item Type: Article
Status: Published
Creators/Authors:
CreatorsEmailPitt UsernameORCID
Wipf, Ppwipf@pitt.eduPWIPF
Xiao, J
Stephenson, CRJ
Date: 1 November 2009
Date Type: Publication
Journal or Publication Title: Chimia
Volume: 63
Number: 11
Page Range: 764 - 775
DOI or Unique Handle: 10.2533/chimia.2009.764
Schools and Programs: Dietrich School of Arts and Sciences > Chemistry
Refereed: Yes
ISSN: 0009-4293
PubMed Central ID: PMC2922051
PubMed ID: 20725595
Date Deposited: 23 Sep 2014 14:43
Last Modified: 16 Mar 2019 14:55
URI: http://d-scholarship.pitt.edu/id/eprint/23058

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