Stereoselective self-sorting in the self-assembly of a Phe–Phe extended guanidiniocarbonyl pyrrole carboxylate zwitterion: formation of two diastereomeric dimers with significantly different stabilities

Abstract

The ‘dipeptide extended’ guanidiniocarbonyl pyrrole carboxylate zwitterion GCP–Phe–Phe 1 forms stable dimers in DMSO. However, dimerization is highly stereoselective. Only homochiral dimers are formed and the (L,L)·(L,L) dimer (K_dim > 10⁵ M⁻¹) is significantly more stable by a factor of 10³ than the diastereomeric (D,L)·(D,L) dimer (K_dim = 120 M⁻¹).