Issue 42, 2022
From the journal:

Organic & Biomolecular Chemistry

Thioether analogues of the pituitary neuropeptide oxytocin via thiol–ene macrocyclisation of unprotected peptides†

Mark D. Nolan, ORCID logo a   Conor Shine, ORCID logo a   Eoin M. Scanlan ORCID logo *a  and  Rita Petracca*b  

* Corresponding authors

a Trinity Biomedical Sciences Institute, Trinity College Dublin, Ireland

b Utrecht University, Utrecht Institute for Pharmaceutical Sciences (UIPS), Chemical Biology and Drug Discovery, Netherlands

Abstract

Disulfide bonds are an essential feature of many bioactive peptides, however, they are labile to reducing conditions which can limit therapeutic application. Herein, we report an efficient methodology for peptide macrocyclisation, furnishing thioether mimetics of disulfide linkages via thiol–ene click chemistry. Furthermore, this methodology is applied to the efficient synthesis of analogues of the neuropeptide oxytocin and in a highly efficient route to the clinical therapeutic carbetocin.

Graphical abstract: Thioether analogues of the pituitary neuropeptide oxytocin via thiol–ene macrocyclisation of unprotected peptides

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Article information

DOI
https://doi.org/10.1039/D2OB01688E
Article type
Communication
Submitted
15 Sep 2022
Accepted
10 Oct 2022
First published
10 Oct 2022
This article is Open Access
Creative Commons BY-NC license

Org. Biomol. Chem., 2022,20, 8192-8196

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Thioether analogues of the pituitary neuropeptide oxytocin via thiol–ene macrocyclisation of unprotected peptides

M. D. Nolan, C. Shine, E. M. Scanlan and R. Petracca, Org. Biomol. Chem., 2022, 20, 8192 DOI: 10.1039/D2OB01688E

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