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Selective Photoredox Trifluoromethylation of Tryptophan‐Containing Peptides
Author(s) -
Ding Bo,
Weng Yue,
Liu Yunqing,
Song Chunlan,
Yin Le,
Yuan Jiafan,
Ren Yanrui,
Lei Aiwen,
Chiang ChienWei
Publication year - 2019
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201901572
Subject(s) - trifluoromethylation , chemistry , tryptophan , combinatorial chemistry , biocompatible material , photoredox catalysis , quenching (fluorescence) , radical , biomolecule , photochemistry , trifluoromethyl , catalysis , fluorescence , photocatalysis , organic chemistry , biochemistry , amino acid , medicine , alkyl , physics , quantum mechanics , biomedical engineering
For application in drug discovery and biomedicine, it is crucial to develop new biocompatible methods to modify polypeptides. Herein, a visible‐light‐induced photoredox trifluoromethylation of tryptophan‐containing peptides is reported. Under a mild, biocompatible, and straightforward condition, this strategy could incorporate the trifluoromethyl group into tryptophan residue with excellent chemo‐ and site‐selectivity. The use of lower photocatalyst loading in 2 mol‐% and cheap CF 3 SO 2 Na salt represents a great catalytic activity and economic CF 3 source. This direct trifluoromethylation strategy allows the ready study of fluorinated peptides exploiting 19 F‐NMR. Additionally, the development of this protocol enables the study of biochemical systems and potentially modulates the function of biomolecules. Careful mechanistic studies (Stern‐Volmer fluorescence quenching, EPR, and radical inhibition/trapping experiments) indicate that the reaction would proceed with a radical–radical cross‐coupling procedure.