Synthetic Study on Selenocystine-Contaning Peptides

Abstract

N-9-Fluorenylmethoxycarbonyl-Se-4-methoxybenzylselenocysteine [Fmoc-Sec(MBzl)-OH] was synthesized from selenocystine and successfully applied to Fmoc-based solid-phase peptide synthesis. The stability and the deprotection conditions of the Se-MBzl group were examined. The diselenide bond of a pepride was directly and effectively established between Sec(MBzl) residues by treatment with iodene or the dimethyl sulfoxide-trifluoroacetic acid system. Reduction kinetics of didelenide and disulfide in model peptides by reduced glutathione were also studied comparatively.