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Photoredox C(2)-Arylation of Indole- and Tryptophan-Containing Biomolecules
Organic Letters ( IF 5.2 ) Pub Date : 2024-05-02 , DOI: 10.1021/acs.orglett.4c01019
Bruno M. da S. Santos 1 , Fernanda G. Finelli 1, 2 , David R. Spring 2
Affiliation  

We introduce a novel and straightforward methodology for photoredox arylation of an indole scaffold using aryldiazonium salts under mild and metal-free conditions. Our approach enables the regioselective and chemoselective introduction of several aryl groups to the C(2) position of indoles and tryptophan, even in competition with other amino acids. This approach extends to the late-stage functionalization of peptides and lysozyme, heralding the unprecedented arylation of tryptophan residues in wild-type proteins and offering broad utility in chemical biology.

中文翻译:

含吲哚和色氨酸的生物分子的光氧化还原 C(2)-芳基化

我们介绍了一种新颖且简单的方法,在温和且无金属的条件下使用芳基重氮盐对吲哚支架进行光氧化还原芳基化。我们的方法能够将多个芳基区域选择性和化学选择性地引入吲哚和色氨酸的 C(2) 位,甚至与其他氨基酸竞争。这种方法扩展到肽和溶菌酶的后期功能化,预示着野生型蛋白质中色氨酸残基前所未有的芳基化,并在化学生物学中提供了广泛的用途。
更新日期:2024-05-02
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