Derivate von L‐Methionin‐sulfoxyd und ihre Verwendung für Peptidsynthesen

The unwanted side reactions often encountered in the synthesis of methionine containing peptides can be eliminated by a temporary conversion of the thioether function of methionine into the sulfoxide at any stage of a peptide synthesis. The sulfoxide oxygen is introduced without the formation of a sulfone when a small excess of hydrogen peroxide is used, and its elimination is easily achieved by reduction with thioglycolic acid. In contrast to the carbobenzoxy derivatives of methionine the removal of the carbobenzoxy group from the corresponding sulfoxides proceeds smoothly by mild treatment with concentrated hydrochloric acid. The synthesis of the peptide derivative H·pro‐Tyr‐Lys(Tos)‐Met·OH, using this method, is described.