Chemical and Ribosomal Synthesis of Topologically Controlled Bicyclic and Tricyclic Peptide Scaffolds Primed by Selenoether Formation.

Autor: Yin, Yizhen, Fei, Qianran, Liu, Weidong, Li, Zhuoru, Suga, Hiroaki, Wu, Chuanliu
Předmět:
Zdroj: Angewandte Chemie International Edition; Apr2019, Vol. 58 Issue 15, p4880-4885, 6p
Abstrakt: Bicyclic and tricyclic peptides have emerged as promising candidates for the development of protein binders and new therapeutics. However, convenient and efficient strategies that can generate topologically controlled bicyclic and tricyclic peptide scaffolds from fully‐unprotected peptides are still much in demand, particularly for those amenable to the design of biosynthetic libraries. In this work, we report a reliable chemical and ribosomal synthesis of topologically controlled bicyclic and tricyclic peptide scaffolds. Our strategy involves the combination of selenoether cyclization followed by disulfide or thioether cyclization, yielding desirable bicyclic and tricyclic peptides. This work thus lays the foundation for developing peptide libraries with controlled topology of multicyclic scaffolds for in vitro display techniques. You'd better shape up: A reliable chemical and ribosomal synthesis of topologically controlled bicyclic and tricyclic peptide scaffolds was developed. Selenoether cyclization was combined with disulfide or thioether cyclization to yield desirable bicyclic and tricyclic peptides. This work lays the foundation for developing peptide libraries with multicyclic scaffolds of controlled topology for in vitro display techniques. [ABSTRACT FROM AUTHOR]
Databáze: Complementary Index