Application of S-1-adamantylcysteine to the synthesis of a 37-residue peptide amide corresponding to human calcitonin gene-related peptide (hCGRP)

Abstract

An S-1-adamantyl (Ad) group on cysteine was found to be cleaved smoothly by 1 M trifluoromethanesulphonic acid–thioanisole in trifluoroacetic acid or thallic trifluoroacetate; the usefulness of Cys(Ad) in practical peptide synthesis was demonstrated by synthesizing human calcitonin gene-related, peptide, a 37-residue peptide amide with one disulphide bridge using a conventional solution method.