AI Article Synopsis
- Researchers developed a method using Rh(III) catalysts to create fluorescent peptides by activating C-H bonds in Phe-based peptides with alkynes.
- The process showcases a wide range of substrates, efficient use of materials, and precision in target selection.
- The resulting fluorescent compounds have strong emission properties and low toxicity, making them suitable for applications in biological studies, specifically targeting lysosomes and mitochondria in live cells.
Article Abstract
Herein, we report a Rh(III)-catalyzed triple C-H activation-annulation of Phe-based peptides with alkynes for the preparation of fluorescent peptides. The robustness of this protocol is reflected by a broad substrate scope, high atom- and step-economy, and excellent chemo- and site-selectivity. An in situ generated polycyclic aromatic hydrocarbon carbocation as a fluorophore exhibits good fluorescence properties (maximum emission wavelength up to 628 nm) and low cell cytotoxicity. The synthetic utility of this method is further demonstrated by versatile product applications in bioconjugation with the protein BSA and specifically targeting lysosomes and mitochondria of live mammalian cells.
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| http://dx.doi.org/10.1021/acs.orglett.4c04081 | DOI Listing |
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