Non-Covalent Interactions Enforce Conformation in Switchable and Water-Soluble Diketopiperazine-Pyridine Foldamers.
Conformation
Crystallography
Foldamers
Molecular Switches
NMR Spectroscopy
Journal
Angewandte Chemie (International ed. in English)
ISSN: 1521-3773
Titre abrégé: Angew Chem Int Ed Engl
Pays: Germany
ID NLM: 0370543
Informations de publication
Date de publication:
28 Aug 2023
28 Aug 2023
Historique:
received:
22
05
2023
medline:
7
7
2023
pubmed:
7
7
2023
entrez:
6
7
2023
Statut:
ppublish
Résumé
To reach their potential as mimics of the dynamic molecules present in biological systems, foldamers must be designed to display stimulus-responsive behavior. Here we report such a foldamer architecture based on alternating pyridine-diketopiperazine linkers. Epimerization is conveniently prevented through a copper-catalyzed coupling protocol. The compounds' native unswitched conformation is first discovered in the solid and solution state. The foldamers can be solubilized in DMSO and pH 9.5 buffer, retaining conformational control to a large degree. Lastly, dynamic switching is demonstrated through treatment with acid, leading to behaviour we describe as stimulus-responsive sidechain reconfiguration.
Identifiants
pubmed: 37414732
doi: 10.1002/anie.202307180
doi:
Types de publication
Journal Article
Langues
eng
Sous-ensembles de citation
IM
Pagination
e202307180Subventions
Organisme : Department for the Economy Northern Ireland (GB)
Organisme : Royal Society of Chemistry
ID : E22-9617192652
Organisme : Engineering and Physical Sciences Research Council
ID : EP/S018077/1
Informations de copyright
© 2023 The Authors. Angewandte Chemie International Edition published by Wiley-VCH GmbH.
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