Self-Synthesizing Models of Helical Proteins Based on Aromatic Disulfide Chemistry.

A new method of synthesis of peptide conjugates with aromatic moieties substituted with two sulfhydryl groups at 1,3-positions is proposed. Amphiphilic peptides derivatized in such a way under oxidative conditions spontaneously form cyclic, covalent trimers and tetramers dominated by α-helical conformations. The tendency to form tri- or tetrahelical bundles depends on sequences of the peptides and on the oxidation conditions, pH, and additives.