Convenient one-pot synthesis of cystine-containing peptides using the trimethylsilyl chloride–dimethyl sulfoxide/trifluoroacetic acid system and its application to the synthesis of bifunctional anti-HIV compounds1

Abstract

A one-pot synthesis of cystine-containing peptides is achieved by treatment of protected peptidyl resins with trimethylsilyl chloride–dimethyl sulfoxide/trifluoroacetic acid in the presence of anisole. This methodology has been successfully applied to the synthesis of highly active anti-HIV peptides conjugated with 3′-azido-3′-deoxythymidine.