Crystallization-induced dynamic resolution and analysis of the non-covalent interactions in the crystal packing of peptide–biphenyl hybrids

Abstract

Dynamic atropselective resolutions of the peptide–biphenyl hybrids 3–5 were achieved by crystallization from methanol solution. These compounds were studied by single-crystal X-ray diffraction. These hybrids crystallize in highly ordered structures kept by an extensive array of intramolecular and intermolecular hydrogen bonds. The solid-state molecular structure is highly dependent on the substituents on the α-carbon of the amino acid. The presence of additional aromatic rings in the side chain causes the molecules in the crystal to interact through a variety of interactions involving the aromatic rings. The resulting supramolecular structures are helices whose orientation depends on the senses of the chirality of the α-carbon of the amino acid residues and the aryl–aryl bond.