Chemoselective Late-Stage Functionalization of Peptides via Photocatalytic C2-Alkylation of Tryptophan.

Lee, Joanna C; Cuthbertson, James D; Mitchell, Nicholas J

Lee, Joanna C; Cuthbertson, James D; Mitchell, Nicholas J.

Afiliación

Lee JC; School of Chemistry, University of Nottingham, University Park, Nottingham NG7 2RD, United Kingdom.
Cuthbertson JD; School of Chemistry, GlaxoSmithKline Carbon Neutral Laboratories for Sustainable Chemistry, University of Nottingham, Jubilee Campus, Nottingham NG7 2TU, United Kingdom.
Mitchell NJ; School of Chemistry, University of Nottingham, University Park, Nottingham NG7 2RD, United Kingdom.

Org Lett ; 25(29): 5459-5464, 2023 07 28.

Article en En | MEDLINE | ID: mdl-37462428

RESUMEN

Across eukaryotic proteomes, tryptophan is the least abundant of the 20 canonical amino acids, which makes it an ideal chemical handle for the late-stage functionalization of peptide and protein scaffolds with minimal production of undesired isoforms. Herein, we report the photocatalytic C2-alkylation of tryptophan using bromodifluoroacetate/acetamide-derived radical precursors. This rapid visible-light-mediated reaction is additive-free, operationally simple, and tolerates diverse functionality. We demonstrate the late-stage modification of a variety of complex peptides, including examples of biological significance.

Asunto(s)

Péptidos; Triptófano; Triptófano/química; Péptidos/química; Proteínas/química; Aminoácidos/química; Alquilación

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Texto completo: 1 Colección: 01-internacional Base de datos: MEDLINE Asunto principal: Péptidos / Triptófano Idioma: En Revista: Org Lett Asunto de la revista: BIOQUIMICA Año: 2023 Tipo del documento: Article País de afiliación: Reino Unido Pais de publicación: Estados Unidos

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