Issue 89, 2022
From the journal:

Chemical Communications

Helical structure in cyclic peptides: effect of N-methyl amides versus esters†

Chongyang Wu,a   Huy N. Hoang, ORCID logo a   Timothy A. Hill, ORCID logo a   Junxian Lim, ORCID logo a   W. Mei Kok,a   Kalyani Akondi,a   Ligong Liu ORCID logo a  and  David P. Fairlie ORCID logo *a  

* Corresponding authors

a Australian Research Council Centre of Excellence for Innovations in Peptide and Protein Science, Institute for Molecular Bioscience, University of Queensland, Brisbane, Qld 4072, Australia
E-mail: d.fairlie@uq.edu.au

Abstract

An alpha helical turn can be reproduced in a cyclic pentapeptide if the first and fifth amino acid sidechains are correctly joined. Here structural studies (CD, NMR, in silico) reveal why N-methylation at positions not involved in hydrogen bonds disrupts helicity whereas ester bonds can maintain helicity and promote greater cell uptake.

Graphical abstract: Helical structure in cyclic peptides: effect of N-methyl amides versus esters

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Article information

DOI
https://doi.org/10.1039/D2CC05092G
Article type
Communication
Submitted
15 Sep 2022
Accepted
13 Oct 2022
First published
24 Oct 2022

Chem. Commun., 2022,58, 12475-12478

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Helical structure in cyclic peptides: effect of N-methyl amides versus esters

C. Wu, H. N. Hoang, T. A. Hill, J. Lim, W. M. Kok, K. Akondi, L. Liu and D. P. Fairlie, Chem. Commun., 2022, 58, 12475 DOI: 10.1039/D2CC05092G

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