Glycylglycine Rotaxanes—The Hydrogen Bond Directed Assembly of Synthetic Peptide Rotaxanes

Abstract

Ringing a peptide (not-so-dumb)bell: the amide groups in the glycylglycine derivative shown below provide the information required to template the formation of benzylic amide macrocycles to yield peptide [2]rotaxanes. The four key hydrogen bonds responsible for cyclization remain intact in the rotaxane in nonpolar solvents, in the solid state, and (when X = N) even in polar solvents such as [D6]DMSO and [D6]DMSO/D2O mixtures. X = CH, N; shaded sphere = Ph2CH, black sphere = Ph2CHCH2.