Selective Photoredox Trifluoromethylation of Tryptophan‐Containing Peptides

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, thi...

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Veröffentlicht in:European journal of organic chemistry 2019-12, Vol.2019 (46), p.7596-7605
Hauptverfasser: Ding, Bo, Weng, Yue, Liu, Yunqing, Song, Chunlan, Yin, Le, Yuan, Jiafan, Ren, Yanrui, Lei, Aiwen, Chiang, Chien‐Wei
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Sprache:eng
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Zusammenfassung: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 CF3SO2Na salt represents a great catalytic activity and economic CF3 source. This direct trifluoromethylation strategy allows the ready study of fluorinated peptides exploiting 19F‐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. The visible‐light‐induced bioconjugation of tryptophan‐containing peptides using of photoredox catalysis is described. The trifluoromethylation proceeds under mild, biocompatible, and straightforward conditions. Using this strategy, the trifluoromethyl group could be incorporated into tryptophan residue with excellent chemo‐ and site‐selectivity.
ISSN:1434-193X
1099-0690
DOI:10.1002/ejoc.201901572