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

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 alpha-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 alpha-carbon of the amino acid residues and the aryl-aryl bond.