Post-Assembly Modification of Head-to-Tail Cyclic Peptides by Methionine-Directed β-C(sp3)–H Arylation,Organic Letters

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Post-Assembly Modification of Head-to-Tail Cyclic Peptides by Methionine-Directed β-C(sp3)–H Arylation
Organic Letters ( IF 4.9 ) Pub Date : 2022-08-02 , DOI: 10.1021/acs.orglett.2c02253
Gang Li ₁ , Feipeng Yuan ₁ , Bo Yao _{1,

2}

Affiliation

Peptide modification by C(sp³)–H functionalization of internal residues remains a major challenge due to the inhibitory effect of peptide bonds. In this work, we developed a methionine-directed β-C(sp³)–H arylation method for internal alanine functionalization. By tuning the σ_C–C bond rotation of internal Ala through head-to-tail cyclization, we overcame the inhibitory effect and functionalized a wide range of head-to-tail cyclic peptides with aryl iodides with excellent position selectivity.

中文翻译：

蛋氨酸定向 β-C(sp3)–H 芳基化对头尾环肽的组装后修饰

由于肽键的抑制作用，通过内部残基的 C(sp ^{3 )-H 官能化进行肽修饰仍然是一项重大挑战。}在这项工作中，我们开发了一种以蛋氨酸为导向的 β-C(sp ³ )-H 芳基化方法，用于内部丙氨酸功能化。通过头尾环化调整内部 Ala 的 σ _C-C键旋转，我们克服了抑制效应，并用芳基碘化物对各种头尾环肽进行了功能化，具有出色的位置选择性。

更新日期：2022-08-02

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