Instituto de Pesquisas de Produtos Naturais, Universidade Federal do Rio de Janeiro, Rio de Janeiro 21941-599, Brazil.
Yusuf Hamied Department of Chemistry, University of Cambridge, Cambridge CB2 1EW, U.K.
Org Lett. 2024 May 17;26(19):4065-4070. doi: 10.1021/acs.orglett.4c01019. Epub 2024 May 2.
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.
我们介绍了一种新颖而直接的方法，用于在温和无金属条件下使用芳基重氮盐对吲哚支架进行光氧化芳基化。我们的方法能够在吲哚和色氨酸的 C(2)位上实现几个芳基的区域选择性和化学选择性引入，即使与其他氨基酸竞争也是如此。该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的空前芳基化，并在化学生物学中具有广泛的应用。
