Oyama Tsuyoshi, Mendive-Tapia Lorena, Cowell Verity, Kopp Adelina, Vendrell Marc, Ackermann Lutz
Institut für Organische und Biomolekulare Chemie, Georg-August-Universität Göttingen Tammanstraße 2 37077 Göttingen Germany
Centre for Inflammation Research, The University of Edinburgh EH16 4TJ Edinburgh UK
Chem Sci. 2023 May 4;14(21):5728-5733. doi: 10.1039/d3sc01868g. eCollection 2023 May 31.
Late-stage diversification of structurally complex amino acids and peptides provides tremendous potential for drug discovery and molecular imaging. Specifically, labeling peptides with fluorescent tags is one of the most important methods for visualizing their mode of operation. Despite major recent advances in the field, direct molecular peptide labeling by C-H activation is largely limited to dyes with relatively short emission wavelengths, leading to high background signals and poor signal-to-noise ratios. In sharp contrast, here we report on the fluorescent labeling of peptides catalyzed by non-toxic manganese(i) C(sp)-H alkenylation in chemo- and site-selective manners, providing modular access to novel near-infrared (NIR) nitrobenzodiazole-based peptide fluorogenic probes.
结构复杂的氨基酸和肽的后期多样化为药物发现和分子成像提供了巨大潜力。具体而言,用荧光标签标记肽是可视化其作用模式的最重要方法之一。尽管该领域最近取得了重大进展,但通过C-H活化进行的直接分子肽标记在很大程度上限于发射波长相对较短的染料,导致高背景信号和低信噪比。与之形成鲜明对比的是,我们在此报告了由无毒锰(I)催化的肽的荧光标记,其以化学和位点选择性方式进行C(sp)-H烯基化反应,提供了模块化地获得基于新型近红外(NIR)硝基苯并二唑的肽荧光探针的途径。