Singlet Oxygen-Induced Furan Oxidation for Site-Specific and Chemoselective Peptide Ligation.
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.
Department of Organic and Macromolecular Chemistry, Ghent University, Krijgslaan 281 S4, 9000, Gent, Belgium.
Eirini
E
Antonatou
Department of Organic and Macromolecular Chemistry, Ghent University, Krijgslaan 281 S4, 9000, Gent, Belgium.|Medical Research Council Laboratory of Molecular Biology, Cambridge, UK.
Kurt
K
Hoogewijs
Department of Chemistry, University of Crete, Vasilika Vouton, 71003, Iraklion, Crete, Greece.
Dimitris
D
Kalaitzakis
Department of Organic and Macromolecular Chemistry, Ghent University, Krijgslaan 281 S4, 9000, Gent, Belgium.
Andreas
A
Baudot
Department of Chemistry, University of Crete, Vasilika Vouton, 71003, Iraklion, Crete, Greece.
Georgios
G
Vassilikogiannakis
Department of Organic and Macromolecular Chemistry, Ghent University, Krijgslaan 281 S4, 9000, Gent, Belgium. annemieke.madder@ugent.be.
Annemieke
A
Madder
D002384:Catalysis; D005456:Fluorescent Dyes / Q000737:chemistry; D005663:Furans / Q000737:chemistry*; D008027:Light; D010084:Oxidation-Reduction; D010455:Peptides / Q000737:chemistry*; D026082:Singlet Oxygen / Q000737:chemistry*
D005456:Fluorescent Dyes; D005663:Furans; D010455:Peptides; D026082:Singlet Oxygen
furan oxidation; hydrazide; peptide labeling; photooxidation; singlet oxygen