Bis (2,2,2-trifluoroethoxy) phosphorochloridate : a new method for the synthesis of peptides

Abstract

The focus of the research presented here is the use of bis (2,2,2trifluoroethoxy) phosphorochloridate as a new coupling reagent for the synthesis of peptides. Bis (2,2,2-trifluoroethoxy) phosphorochloridate is modeled after diethyl phosphorocyanide (DEPC). DEPC converts the carboxyl portion of an amino acid to an O-acyl phosphate, which acts as a leaving group when attacked by a good nucleophile such as an amino group from a second amino acid, resulting in the formation of a peptide. The trifluoroethyl groups would enhance the electrophilicity of the phosphorus, thus increasing the yield of the intermediate, O-acyl phosphate, and augment the leaving group ability of the phosphate moiety in the peptide coupling.