Dynamic Approach to Synthetic Lectin for Glucose with Boosted Binding Affinity through C-H Hydrogen Bonds.
Chemistry
; 29(32): e202300524, 2023 Jun 07.
Article
en En
| MEDLINE
| ID: mdl-36913252
ABSTRACT
A biomimetic receptor for glucose has been developed with high affinity and selectivity. The receptor was efficiently synthesized in three steps through dynamic imine chemistry followed by imine-to-amide oxidation. The receptor features two parallel durene panels, forming a hydrophobic pocket for [CHâ
â
â
π] interactions, and two pyridinium residues directing four amide bonds towards the pocket. These pyridinium residues not only improve solubility but also provide polarized C-H bonds for hydrogen bonding. Experimental data and DFT calculations show that these polarized C-H bonds significantly enhance substrate binding. These findings demonstrate the power of dynamic covalent chemistry for creating molecular receptors and using polarized C-H bonds for boosted carbohydrate recognition in water, providing a foundation for developing glucose-responsive materials and sensors.
Palabras clave
Texto completo:
1
Banco de datos:
MEDLINE
Asunto principal:
Glucosa
/
Lectinas
Idioma:
En
Año:
2023
Tipo del documento:
Article