Reaction, Recognition, Relay: Anhydride Hydrolysis Reported by Conformationally Responsive Fluorinated Foldamers in Micelles.
Angew Chem Int Ed Engl
; 63(30): e202405924, 2024 Jul 22.
Article
em En
| MEDLINE
| ID: mdl-38703400
ABSTRACT
Natural membrane receptors are proteins that can report on changes in the concentration of external chemical messengers. Messenger binding to a receptor produces conformational changes that are relayed through the membrane into the cell; this information allows cells to adapt to changes in their environment. Artificial membrane receptors (R)-1 and (S)-1 are helical α-aminoisobutyric acid (Aib) foldamers that replicate key parts of this information relay. Solution-phase 19Fâ
NMR spectroscopy of zinc(II)-capped receptor 1, either in organic solvent or in membrane-mimetic micelles, showed messenger binding produced an enrichment of either left- or right-handed screw-sense; the chirality of the bound messenger was relayed to the other receptor terminus. Furthermore, in situ production of a chemical messenger in the external aqueous environment could be detected in real-time by a racemic mixture of receptor 1 in micelles. The hydrolysis of insoluble anhydrides produced carboxylate in the aqueous phase, which bound to the receptors and gave a distinct 19Fâ
NMR output from inside the hydrophobic region of the micelles.
Palavras-chave
Texto completo:
1
Base de dados:
MEDLINE
Assunto principal:
Anidridos
/
Micelas
Idioma:
En
Ano de publicação:
2024
Tipo de documento:
Article