Issue 83, 2004

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 peptidebiphenyl 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 arylaryl bond.

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

Article information

Article type
Paper
Submitted
04 may. 2004
Accepted
03 jun. 2004
First published
17 sep. 2004

CrystEngComm, 2004,6, 513-521

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

B. Herradón, A. Montero, E. Mann and M. A. Maestro, CrystEngComm, 2004, 6, 513 DOI: 10.1039/B406652A

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