Aromatic Ring-Fused Amidine Based Allosteric Receptors Activated by Guest-Induced π-Conjugation Switching.
allosteric effect
cooperativity
hydrogen bond
molecular recognition
π-conjugation
Journal
ChemPlusChem
ISSN: 2192-6506
Titre abrégé: Chempluschem
Pays: Germany
ID NLM: 101580948
Informations de publication
Date de publication:
27 Oct 2024
27 Oct 2024
Historique:
received:
18
09
2024
accepted:
24
10
2024
medline:
27
10
2024
pubmed:
27
10
2024
entrez:
27
10
2024
Statut:
aheadofprint
Résumé
Amidine-substituted allosteric receptors 2a and 2b for benzenediols were synthesized. Receptor 2a with five-membered amidines exhibited greater allostericity than the amide-substituted receptor 1, while 2b with six-membered amidines exhibited less allostericity. NMR titration experiments revealed that a significant enthalpic factor was involved in the allostericity of these receptors. X-ray and DFT optimized structures of 2a and 2b revealed that 2a adopted a coplanar conformation with π-conjugation between the amidines and the phenylene ring of the hydrindacene framework, resulting in high allostericity due to inactivation of the initial binding.
Identifiants
pubmed: 39462205
doi: 10.1002/cplu.202400612
doi:
Types de publication
Journal Article
Langues
eng
Sous-ensembles de citation
IM
Pagination
e202400612Informations de copyright
© 2024 Wiley‐VCH GmbH.