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Photochemical Chemoselective Alkylation of Tryptophan-Containing Peptides

We report a photochemical method for the chemoselective radical functionalization of tryptophan (Trp)-containing peptides. The method exploits the photoactivity of an electron donor–acceptor complex generated between the tryptophan unit and pyridinium salts. Irradiation with weak light (390 nm) generates radical intermediates right next to the targeted Trp amino acid, facilitating a proximity-driven radical functionalization. This protocol exhibits high chemoselectivity for Trp residues over other amino acids and tolerates biocompatible conditions.

Laroche, B.; Tang, X.; Archer, G.; Di Sanza, R.; Melchiorre, P.

Org. Lett. 2021, 23 (2), 285–289
DOI: 10.1021/acs.orglett.0c03735

Observations

*Among the top 3 recently published most-read articles for January in Organic Letters

 

Associated ICIQ research group/s:

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