A General Synthesis Approach to Double-Guanidinium Stapled Peptides and Foldamers.

ABSTRACT: In the broader context of peptide macrocyclization, methods enabling the formation of specific crosslinks between orthogonally protected, amino-functionalized side chains (e.g., Lys-Lys crosslinks) are of potential interest for expanding molecular diversity and stabilizing peptide secondary structures. We recently introduced a solid-phase synthesis approach for the rapid generation of guanidinium stapled helical peptides and have shown their utility for inhibition of protein-protein interactions. Whereas our previous work concentrated on the formation of mono-guanidinium crosslinks, we show here that we can expand this approach to prepare bis-guanidinium stapled peptides and foldamers on-resin. The methodology similarly uses two orthogonally protected amino-functionalized side chains and f

SUBMITTER: Neuville M 

PROVIDER: S-EPMC12598378 | biostudies-literature | 2025 Nov

REPOSITORIES: biostudies-literature