Chemical and Ribosomal Synthesis of Topologically Controlled Bicyclic and Tricyclic Peptide Scaffolds Primed by Selenoether Formation.,Angewandte Chemie International Edition

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Chemical and Ribosomal Synthesis of Topologically Controlled Bicyclic and Tricyclic Peptide Scaffolds Primed by Selenoether Formation.
Angewandte Chemie International Edition ( IF 16.1 ) Pub Date : 2019-03-12 , DOI: 10.1002/anie.201813827
Yizhen Yin ₁ , Qianran Fei ₂ , Weidong Liu ₂ , Zhuoru Li ₂ , Hiroaki Suga ₁ , Chuanliu Wu ₂

Affiliation

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.

中文翻译：

硒醚形成引发的拓扑控制双环和三环肽支架的化学和核糖体合成。

双环和三环肽已成为开发蛋白结合剂和新疗法的有前途的候选者。但是，仍然需要大量方便，有效的策略来从完全未保护的肽生成拓扑控制的双环和三环肽支架，特别是对于那些适合于生物合成文库设计的策略。在这项工作中，我们报告了拓扑受控的双环和三环肽支架的可靠的化学和核糖体合成。我们的策略包括结合硒醚环化，然后进行二硫键或硫醚环化，从而产生所需的双环和三环肽。因此，这项工作为开发具有受控多环支架拓扑结构的肽库奠定了基础，以用于体外展示技术。

更新日期：2019-03-12

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