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Singlet Oxygen-Induced Furan Oxidation for Site-Specific and Chemoselective Peptide Ligation
Eirini Antonatou1, Kurt Hoogewijs1,2, Dimitris Kalaitzakis3
1Department of Organic and Macromolecular Chemistry, Ghent University, Krijgslaan 281 S4, 9000, Gent, Belgium.
Abstract:
A novel chemoselective ligation methodology has been developed for the facile construction of peptide-based fluorescent probes. Furan-containing peptides were activated by singlet oxygen and covalently engaged by nitrogen nucleophiles to yield stable conjugates. Singlet oxygen was compatible with sensitive amino acid residues within the peptides and a range of fluorophores, bearing different functionalities, were successfully incorporated, illustrating the broad scope of the developed strategy.
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