Polymer Supported Methionine Selenoxide as an Excellent Immobilized Oxidant for the Formation of Disulfide Bonds in Peptides

摘要

Two PEG-based polymer supported methionine selenoxide (MeSeO) named TentaGel-MetSeO and PEG-MetSeO were synthesized and used as immobilized oxidants for the purpose of formation of disulfide bonds in peptides under aqueous conditions. Peptide disulfide bonds were successfully synthesized by use of the two immobilized oxidants. Moreover, the oxidation of the methionine residue to its sulfoxide derivate was not observed. By comparison, the yield of disulfide-containing peptide via PEG-MetSeO oxidation is higher than that of the disulfide-containing peptide via TentaGel-MetSeO oxidation. PEG-MetSeO can be used at least 10 cycles without the significant yield decrease. The two immobilized oxidants can be separated from the reaction mixture using filtration, making the peptide synthesis more easily.