Peptide cyclisation promoted by supramolecular complex formation

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...

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Autores principales: Hartendorp, Arnout P. T., de Zwart, Felix J., Bieräugel, Hans, de Bruin, Bas, Reek, Joost N. H., van Maarseveen, Jan H.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: The Royal Society of Chemistry 2021
Materias:
Chemistry
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8767553/
https://www.ncbi.nlm.nih.gov/pubmed/34935833
http://dx.doi.org/10.1039/d1ob02309h
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author Hartendorp, Arnout P. T.
de Zwart, Felix J.
Bieräugel, Hans
de Bruin, Bas
Reek, Joost N. H.
van Maarseveen, Jan H.
author_facet Hartendorp, Arnout P. T.
de Zwart, Felix J.
Bieräugel, Hans
de Bruin, Bas
Reek, Joost N. H.
van Maarseveen, Jan H.
author_sort Hartendorp, Arnout P. T.
collection PubMed
description 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%.
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spelling pubmed-87675532022-02-15 Peptide cyclisation promoted by supramolecular complex formation Hartendorp, Arnout P. T. de Zwart, Felix J. Bieräugel, Hans de Bruin, Bas Reek, Joost N. H. van Maarseveen, Jan H. Org Biomol Chem Chemistry 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%. The Royal Society of Chemistry 2021-12-16 /pmc/articles/PMC8767553/ /pubmed/34935833 http://dx.doi.org/10.1039/d1ob02309h Text en This journal is © The Royal Society of Chemistry https://creativecommons.org/licenses/by-nc/3.0/
spellingShingle Chemistry
Hartendorp, Arnout P. T.
de Zwart, Felix J.
Bieräugel, Hans
de Bruin, Bas
Reek, Joost N. H.
van Maarseveen, Jan H.
Peptide cyclisation promoted by supramolecular complex formation
title Peptide cyclisation promoted by supramolecular complex formation
title_full Peptide cyclisation promoted by supramolecular complex formation
title_fullStr Peptide cyclisation promoted by supramolecular complex formation
title_full_unstemmed Peptide cyclisation promoted by supramolecular complex formation
title_short Peptide cyclisation promoted by supramolecular complex formation
title_sort peptide cyclisation promoted by supramolecular complex formation
topic Chemistry
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8767553/
https://www.ncbi.nlm.nih.gov/pubmed/34935833
http://dx.doi.org/10.1039/d1ob02309h
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