Conformation and structure of acidic dipeptides. Crystal structures of L-alanyl-L-aspartic acid and alpha-L-glutamyl-L-aspartic acid. 1983

D S Eggleston, and D J Hodgson

The crystal structures of the dipeptides L-alanyl-L-aspartic acid, C7H12N2O5, and alpha-L-glutamyl-L-aspartic acid, C9H14N2O7, have been determined from three-dimensional X-ray diffractometer data. Alanylaspartic acid crystallizes in the orthorhombic space group P2(1)2(1)2(1) with four formula units in a cell of dimensions a = 13.389(5), b = 14.467(3), c = 4.781(1) A. Glutamylaspartic acid also crystallizes in space group P2(1)2(1)2(1) with four formula units in a cell of dimensions a = 13.709(5), b = 16.126(7), c = 4.939(5) A. Both structures were solved by direct methods and refined by full-matrix least squares methods; the final value of the weighted R-factors (on F) were 0.040 based on 790 independent intensities with I greater than or equal to 2 sigma (I) for Ala-Asp and 0.033 based on 1105 intensities with I greater than or equal to 2 sigma (I) for Glu-Asp. Each dipeptide occurs as a zwitterion with the amino terminus protonated and the main chain carboxyl group deprotonated. The conformation of the peptide linkage is trans in both molecules, the omega torsion angle being - 175.9 degrees in Ala-Asp and 174.3 degrees in Glu-Asp. There is considerable intermolecular, but not intramolecular, hydrogen bonding in the crystals. The conformations and structures of Ala-Asp and Glu-Asp are compared to those of other structurally characterized acidic dipeptides.

UI MeSH Term Description Entries
D008958 Models, Molecular Models used experimentally or theoretically to study molecular shape, electronic properties, or interactions; includes analogous molecules, computer-generated graphics, and mechanical structures. Molecular Models,Model, Molecular,Molecular Model
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
D013329 Structure-Activity Relationship The relationship between the chemical structure of a compound and its biological or pharmacological activity. Compounds are often classed together because they have structural characteristics in common including shape, size, stereochemical arrangement, and distribution of functional groups. Relationship, Structure-Activity,Relationships, Structure-Activity,Structure Activity Relationship,Structure-Activity Relationships
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

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