ArticleOrganic letters2023
Chemoselective Late-Stage Functionalization of Peptides via Photocatalytic C2-Alkylation of Tryptophan.
Article in Organic letters, 2023. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 8 papers.
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Who cites it
8 citing papers in PubMed.
- Introducing azobenzenes as solid phase peptide synthesis linkers.RSC chemical biology · 2026Article
- C-C Bond Formation via Direct Functionalization of Indolizines with a Bichromophoric Ruthenium Photocatalyst.ACS organic & inorganic Au · 2026Article
- Recent Advances in Bioconjugation of Aromatic Amino Acid Residues by a Reactivity-Guided Approach.Chemical record (New York, N.Y.) · 2026Review
- Photocatalytic Synthesis of Difluorinated Glycoamino Acids and Neoglycopeptides via Hydrodifluoroacetamidation of Vinyl-C-glycosides.The Journal of organic chemistry · 2025Article
- Transformation-Guided Genome Mining Provides Access to Brominated Lanthipeptides.Organic letters · 2025Article
- Halogenase-Assisted Alkyne/Aryl Bromide Sonogashira Coupling for Ribosomally Synthesized Peptides.Journal of the American Chemical Society · 2024Article
- Clickable tryptophan modification for late-stage diversification of native peptides.Science advances · 2024Article
- Photoredox C(2)-Arylation of Indole- and Tryptophan-Containing Biomolecules.Organic letters · 2024Article
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Authors and funding
3 authors.
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Abstract
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.
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