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alpha,beta-Dehydro-amino acid residues in the design of peptide structures: synthesis, crystal structure, and molecular conformation of two homologous peptides-N-Ac-dehydro-Phe-L-Leu-OCH3 and N-Ac-dehydro-Phe-NorVal-OCH3. 1994

P Sharma, and P Narula, and T P Singh
Department of Biophysics, All India Institute of Medical Sciences, New Delhi.

The dehydro-residue containing peptides N-Ac-dehydro-Phe-L-Leu-OCH3 (I) and N-Ac-dehydro-Phe-NorVal-OCH3 (II) were synthesized by the usual workup procedures. The peptides crystallize from their solutions in methanol in space group P6(5): (I) a = b = 12.528(2) A, c = 21.653(5) A; (II) a = b = 12.532(2) A, c = 21.695(4) A. The structures were determined by direct methods. Both peptides adopt similar conformations with phi,psi of dehydro-Phe as follows: (I) -57.0(5) degrees and -37.0(5) degrees; (II) -56.0(5), degrees, and -37.5(5) degrees. The observed data on dehydro-Phe when placed at the (i + 1) position show that the phi,psi values of dehydro-Phe are either -60 degrees, 140 degrees or -60 degrees, -30 degrees. The conformation of -60 degrees, 140 degrees can be accommodated only with a flexible residue at the (i + 2) position while the phi,psi values of -60 degrees, -30 degrees are obtained with a bulky residue at the (i + 2) position as in the present structures. The molecules are packed in a helical way along the c axis. These are held by two strong intermolecular hydrogen bonds involving both NH as donors and acetyl group and dehydro-Phe oxygen atoms as acceptors.

UI MeSH Term Description Entries
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
D004151 Dipeptides Peptides composed of two amino acid units. Dipeptide
D000596 Amino Acids Organic compounds that generally contain an amino (-NH2) and a carboxyl (-COOH) group. Twenty alpha-amino acids are the subunits which are polymerized to form proteins. Amino Acid,Acid, Amino,Acids, Amino
D017386 Sequence Homology, Amino Acid The degree of similarity between sequences of amino acids. This information is useful for the analyzing genetic relatedness of proteins and species. Homologous Sequences, Amino Acid,Amino Acid Sequence Homology,Homologs, Amino Acid Sequence,Homologs, Protein Sequence,Homology, Protein Sequence,Protein Sequence Homologs,Protein Sequence Homology,Sequence Homology, Protein,Homolog, Protein Sequence,Homologies, Protein Sequence,Protein Sequence Homolog,Protein Sequence Homologies,Sequence Homolog, Protein,Sequence Homologies, Protein,Sequence Homologs, Protein
D018360 Crystallography, X-Ray The study of crystal structure using X-RAY DIFFRACTION techniques. (McGraw-Hill Dictionary of Scientific and Technical Terms, 4th ed) X-Ray Crystallography,Crystallography, X Ray,Crystallography, Xray,X Ray Crystallography,Xray Crystallography,Crystallographies, X Ray,X Ray Crystallographies

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