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Published on: June 21, 2017
Lighting up peptides: direct dehydroalanine formation from diselenides via Rose Bengal photocatalysis
Mateusz Waliczek1, Martyna Strączek1, Piotr Stefanowicz1
1Faculty of Chemistry, University of Wrocław, Joliot-Curie 14 Street, 50-383 Wrocław, Poland. mateusz.waliczek2@uwr.edu.pl.
Abstract:
A visible-light-driven method for the site-selective conversion of diselenide-containing peptides to dehydroalanine (Dha) is presented. Using Rose Bengal as a photosensitizer in aqueous conditions, this photocatalytic process proceeds via oxidative cleavage of the Se-Se bond followed by β-elimination to afford Dha with high yield and chemoselectivity. This mild and bioorthogonal strategy enables downstream peptide functionalization and offers a practical route for post-synthetic peptide editing.
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