Substituted Phenylsulfenyl Groups for Amino Protection during Peptide Synthesis

Abstract

Several substituted phenylsulfenyl chlorides were synthesized for the investigation of the properties of sulfenyl N-protecting groups and new sulfenyl (o-nitrophenylsulfenyl and 2, 4-dinitrophenylsulfenyl) derivatives of some amino acids were obtained. The disubstituted phenylsulfenyl derivatives were far more stable than the monosubstituted ones in 80% acetic acid. Thus the sulfenyl derivatives of S-benzyl-L-cysteine was synthesized in pure state and used successfully to form cysteinyl peptides.