Electrochemical synthesis of peptide aldehydes via CâN bond cleavage of cyclic amines.
Nat Commun
; 15(1): 5181, 2024 Jun 18.
Article
en En
| MEDLINE
| ID: mdl-38890290
ABSTRACT
Peptide aldehydes are crucial biomolecules essential to various biological systems, driving a continuous demand for efficient synthesis methods. Herein, we develop a metal-free, facile, and biocompatible strategy for direct electrochemical synthesis of unnatural peptide aldehydes. This electro-oxidative approach enabled a step- and atom-economical ring-opening via CâN bond cleavage, allowing for homoproline-specific peptide diversification and expansion of substrate scope to include amides, esters, and cyclic amines of various sizes. The remarkable efficacy of the electro-synthetic protocol set the stage for the efficient modification and assembly of linear and macrocyclic peptides using a concise synthetic sequence with racemization-free conditions. Moreover, the combination of experiments and density functional theory (DFT) calculations indicates that different N-acyl groups play a decisive role in the reaction activity.
Texto completo:
1
Base de datos:
MEDLINE
Asunto principal:
Péptidos
/
Aldehídos
/
Técnicas Electroquímicas
/
Aminas
Idioma:
En
Revista:
Nat Commun
Asunto de la revista:
BIOLOGIA
/
CIENCIA
Año:
2024
Tipo del documento:
Article