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Design of peptides using alpha, beta-dehydro-residues: synthesis, crystal structure and molecular conformation of N-Boc-L-Val-delta Phe-delta Phe-L-Ala-OCH3. 1996

S Bhatia, and S Dey, and P Kaur, and T P Singh
Department of Biophysics, All India Institute of Medical Sciences, New Delhi, India.

To obtain general rules of peptide design using alpha, beta-dehydro-residues, a sequence with two consecutive delta Phe-residues, Boc-L-Val-delta Phe-delta Phe-L-Ala-OCH3, was synthesized by azlactone method in solution phase. The peptide was crystallized form its solution in an acetone/water mixture (70:30) in space group P6(1) with a = b = 14.912(3) A, c = 25.548(5) A, V = 4912.0(6) A3. The structure was determined by direct methods and refined by a full matrix least-squares procedure to an R value of 0.079 for 2891 observed [I > or = 3 delta (1)] reflections. The backbone torsion angles phi 1 = 54(1) degrees, psi 1 = 129(1) degrees, omega 1 = -177(1) degrees, phi 2 = 57(1) degrees, psi 2 = 15(1) degrees, omega 2 = -170(1) degrees, phi 3 = 80(1) degrees, psi 3 = 7(2) degrees, omega 3 = -177(1) degrees, phi 4 = -108(1) degrees and psi T4 = -34(1) degrees suggest that the peptide adopts a folded conformation with two overlapping beta-turns of types II and III'. These turns are stabilized by two intramolecular hydrogen bonds between the CO of the Boc group and the NH of delta Phe3 and the CO of Val1 and the NH of Ala4. The torsion angles of delta Phe2 and delta Phe3 side chains are similar and indicate that the two delta Phe residues are essentially planar. The folded molecules from head-to-tail intermolecular hydrogen bonds giving rise to continuous helical columns which run parallel to the c-axis. This structure established the formation of two beta-turns of types II and III' respectively for sequences containing two consecutive delta Phe residues at (i + 2) and (i + 3) positions with a branched beta-carbon residue at one end of the tetrapeptide.

UI MeSH Term Description Entries
D009842 Oligopeptides Peptides composed of between two and twelve amino acids. Oligopeptide
D010455 Peptides Members of the class of compounds composed of AMINO ACIDS joined together by peptide bonds between adjacent amino acids into linear, branched or cyclical structures. OLIGOPEPTIDES are composed of approximately 2-12 amino acids. Polypeptides are composed of approximately 13 or more amino acids. PROTEINS are considered to be larger versions of peptides that can form into complex structures such as ENZYMES and RECEPTORS. Peptide,Polypeptide,Polypeptides
D010649 Phenylalanine An essential aromatic amino acid that is a precursor of MELANIN; DOPAMINE; noradrenalin (NOREPINEPHRINE), and THYROXINE. Endorphenyl,L-Phenylalanine,Phenylalanine, L-Isomer,L-Isomer Phenylalanine,Phenylalanine, L Isomer
D011487 Protein Conformation The characteristic 3-dimensional shape of a protein, including the secondary, supersecondary (motifs), tertiary (domains) and quaternary structure of the peptide chain. PROTEIN STRUCTURE, QUATERNARY describes the conformation assumed by multimeric proteins (aggregates of more than one polypeptide chain). Conformation, Protein,Conformations, Protein,Protein Conformations
D003460 Crystallization The formation of crystalline substances from solutions or melts. (McGraw-Hill Dictionary of Scientific and Technical Terms, 4th ed) Crystalline Polymorphs,Polymorphism, Crystallization,Crystal Growth,Polymorphic Crystals,Crystal, Polymorphic,Crystalline Polymorph,Crystallization Polymorphism,Crystallization Polymorphisms,Crystals, Polymorphic,Growth, Crystal,Polymorph, Crystalline,Polymorphic Crystal,Polymorphisms, Crystallization,Polymorphs, Crystalline
D006860 Hydrogen Bonding A low-energy attractive force between hydrogen and another element. It plays a major role in determining the properties of water, proteins, and other compounds. Hydrogen Bonds,Bond, Hydrogen,Hydrogen Bond
D014961 X-Ray Diffraction The scattering of x-rays by matter, especially crystals, with accompanying variation in intensity due to interference effects. Analysis of the crystal structure of materials is performed by passing x-rays through them and registering the diffraction image of the rays (CRYSTALLOGRAPHY, X-RAY). (From McGraw-Hill Dictionary of Scientific and Technical Terms, 4th ed) Xray Diffraction,Diffraction, X-Ray,Diffraction, Xray,Diffractions, X-Ray,Diffractions, Xray,X Ray Diffraction,X-Ray Diffractions,Xray Diffractions
D015195 Drug Design The molecular designing of drugs for specific purposes (such as DNA-binding, enzyme inhibition, anti-cancer efficacy, etc.) based on knowledge of molecular properties such as activity of functional groups, molecular geometry, and electronic structure, and also on information cataloged on analogous molecules. Drug design is generally computer-assisted molecular modeling and does not include PHARMACOKINETICS, dosage analysis, or drug administration analysis. Computer-Aided Drug Design,Computerized Drug Design,Drug Modeling,Pharmaceutical Design,Computer Aided Drug Design,Computer-Aided Drug Designs,Computerized Drug Designs,Design, Pharmaceutical,Drug Design, Computer-Aided,Drug Design, Computerized,Drug Designs,Drug Modelings,Pharmaceutical Designs

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