Structured cyclic peptide mimics by chemical ligation

Atkinson, B. C. and Thomson, A. R. (2022) Structured cyclic peptide mimics by chemical ligation. Peptide Science, (doi: 10.1002/pep2.24266) (Early Online Publication)

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Abstract

We report the development of a β-turn mimic that allows the direct formation of cyclic peptides through a spontaneous cyclisation under standard solid phase peptide synthesis (SPPS) cleavage conditions. The mimic is formed via an acylhydrazone, which is either reduced in situ by triisopropylsilane-trifluoroacetic acid, or which can be isolated and reduced in a separate step. This method uses commercially available reagents and is compatible with manual and automated SPPS methods. The cyclisation is tolerant of polar residues at the C-terminal position, with the exception of asparagine, for which a subsequent structural rearrangement similar to aspartimide formation was observed. The cyclisation method has been shown to tolerate ring sizes equivalent to 5–10 amino acid residues. We have used this method to design and synthesise potential selective integrin binding sequences with controlled conformations.

Item Type:Articles
Status:Early Online Publication
Refereed:Yes
Glasgow Author(s) Enlighten ID:Atkinson, Ms Bethany and Thomson, Dr Drew
Authors: Atkinson, B. C., and Thomson, A. R.
College/School:College of Science and Engineering > School of Chemistry
Journal Name:Peptide Science
Publisher:Wiley
ISSN:2475-8817
ISSN (Online):2475-8817
Published Online:23 March 2022
Copyright Holders:Copyright © 2022 The Authors
First Published:First published in Peptide Science 2022
Publisher Policy:Reproduced under a Creative Commons licence

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