Intramolecular addition of cysteine thiyl radicals to phenylalanine in peptides: formation of cyclohexadienyl type radicals.
The intra-molecular addition of peptide cysteine thiyl radicals to phenylalanine yields alkylthio-substituted cyclohexadienyl radicals for the peptides Phe-Cys and Phe-Gly-Cys-Gly, i.e. even when Phe and Cys are separated by a Gly residue, and presents a possible free radical pathway to thioether-containing peptide and protein cross-links.
Nauser
Thomas
T
Laboratory of Inorganic Chemistry ETH Zürich, CH-8093, Zürich, Switzerland.
Casi
Giulio
G
Koppenol
Willem H
WH
Schöneich
Christian
C
D053138:Cyclohexenes / Q000737:chemistry*; D003545:Cysteine / Q000737:chemistry*; D005609:Free Radicals / Q000138:chemical synthesis*; D010455:Peptides / Q000138:chemical synthesis / Q000737:chemistry*; D010649:Phenylalanine / Q000737:chemistry*
D053138:Cyclohexenes; D005609:Free Radicals; D010455:Peptides; D010649:Phenylalanine; D003545:Cysteine