title: 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) > 10(5) M(-1)) is significantly more stable by a factor of 10(3) than the diastereomeric (D,L)·(D,L) dimer (K(dim) = 120 M(-1)).
authors.affiliation: University of Duisburg-Essen, Faculty of Chemistry, Universitaetsstraße 7, 45141 Essen, Germany.
authors.forename: Fabian
authors.initials: F
authors.lastname: Rodler
authors.forename: Wilhelm
authors.initials: W
authors.lastname: Sicking
authors.forename: Carsten
authors.initials: C
authors.lastname: Schmuck
mesh_terms: D002264:Carboxylic Acids / Q000737:chemistry*; D019281:Dimerization; D004151:Dipeptides / Q000737:chemistry*; D008958:Models, Molecular; D008968:Molecular Conformation; D010649:Phenylalanine / Q000737:chemistry*; D013237:Stereoisomerism; D013379:Substrate Specificity
chemical_list: D002264:Carboxylic Acids; D004151:Dipeptides; C562088:guanidiniocarbonyl pyrrole carboxylate-phenylalanyl-phenylalanine; D010649:Phenylalanine