Issue 3, 2022
From the journal:

Organic & Biomolecular Chemistry

Peptide cyclisation promoted by supramolecular complex formation†

Arnout P. T. Hartendorp,a   Felix J. de Zwart, ORCID logo a   Hans Bieräugel,a   Bas de Bruin, ORCID logo a   Joost N. H. Reek ORCID logo a  and  Jan H. van Maarseveen ORCID logo *a  

* Corresponding authors

a Van‘t Hoff Institute for Molecular Sciences (HIMS), Science Park 904, 1098 XH Amsterdam, The Netherlands
E-mail: j.h.vanmaarseveen@uva.nl

Abstract

Phenol ester activated dipeptides that are reluctant to ring-close have been cyclised with the aid of sterically shielding metallo-porphyrins avoiding unwanted intermolecular reactions. The binding of ZnTPP to the dipyridine-functionalised activating phenolic ester was studied by NMR titrations and modelling. Staudinger-mediated cyclisations in the presence of ZnTPP increased the yield of the cyclic dipeptide from 16% to 40%.

Graphical abstract: Peptide cyclisation promoted by supramolecular complex formation

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Article information

DOI
https://doi.org/10.1039/D1OB02309H
Article type
Communication
Submitted
25 Nov. 2021
Accepted
16 Dec. 2021
First published
16 Dec. 2021
This article is Open Access
Creative Commons BY-NC license

Org. Biomol. Chem., 2022,20, 575-578

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Peptide cyclisation promoted by supramolecular complex formation

A. P. T. Hartendorp, F. J. de Zwart, H. Bieräugel, B. D. Bruin, J. N. H. Reek and J. H. van Maarseveen, Org. Biomol. Chem., 2022, 20, 575 DOI: 10.1039/D1OB02309H

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