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Recent Advances in the Synthesis of Peptoid Macrocycles

Webster, A.M.; Cobb, S.L.

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Authors

A.M. Webster



Abstract

Over the past two decades, developing medical applications for peptides has, and continues to be a highly active area of research. At present there are over 60 peptide-based drugs on the market and more than 140 in various stages of clinical trials. The interest in peptide-based therapeutics arises from their biocompatibility and their ability to form defined secondary and tertiary structures, resulting in a high selectivity for complex targets. However, there are significant challenges associated with the development of peptide-based therapeutics, namely peptides are readily metabolised in vivo. Peptoids are an emerging class of peptidomimetic and they offer an alternative to peptides. Peptoids are comprised of N-substituted glycines where side-chains are located on the nitrogen atom of the amide backbone rather than the α-carbon as is the case in peptides. This change in structure confers a high degree of resistance to proteolytic degradation but the absence of any backbone hydrogen bonding means that peptoids exhibit a high degree of conformational flexibility. Cyclisation has been explored as one possible route to rigidify peptoid structures, making them more selective, and, therefore more desirable as potential therapeutics. This review outlines the various strategies that have been developed over the last decade to access new types of macrocyclic peptoids.

Citation

Webster, A., & Cobb, S. (2018). Recent Advances in the Synthesis of Peptoid Macrocycles. Chemistry - A European Journal, 24(30), 7560-7573. https://doi.org/10.1002/chem.201705340

Journal Article Type Article
Acceptance Date Jan 10, 2018
Online Publication Date Feb 21, 2018
Publication Date May 28, 2018
Deposit Date Dec 21, 2017
Publicly Available Date Mar 29, 2024
Journal Chemistry - A European Journal
Print ISSN 0947-6539
Electronic ISSN 1521-3765
Publisher Wiley
Peer Reviewed Peer Reviewed
Volume 24
Issue 30
Pages 7560-7573
DOI https://doi.org/10.1002/chem.201705340

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Copyright Statement
© 2018 The Authors. Published by Wiley-VCH Verlag GmbH & Co. KGaA. This is an open access article under the terms of the Creative Commons Attribution License, which permits use, distribution and reproduction in any medium, provided the original work is properly cited.







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