Crystal and molecular structure of Boc-D-Ala-delta Phe-Gly-delta Phe- D-Ala-OMe: a 3 10-helical dehydropeptide

Biopolymers
M R CiajoloO Pieroni

Abstract

The crystal and molecular structure of the pentapeptide Boc-D-Ala-delta Phe-Gly-delta Phe-D-Ala-OMe, containing two dehydrophenylalanine residues, was determined by x-ray diffraction. The molecule crystallizes in the orthorombic P2(1)2(1)2(1) space group, with a = 10.439(3), b = 15.319(3) and c = 21.099(4) A. In the solid state, the conformation of the pentapeptide is characterized by the presence of two type III' beta-turns. Thus the peptide assumes a left-handed 3(10-helical conformation, the left sense being due to the D configuration of the alanine residues. The two unsaturated residues are located in the (i + 1) position of the first beta-turn and in the (i + 2) position of the second beta-turn, respectively. In the crystal, the helical molecules are linked head to tail by hydrogen bonds. Lateral hydrogen bonds are also formed between molecules related by a twofold screw symmetry. This gives rise to a typical mode of packing characterized by infinite helical "chains,' similar to the packing found in other oligopeptides that adopt a 3(10)-helical structure.

References

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Citations

Jan 1, 1996·Biopolymers·O PieroniV S Chauhan
Jan 1, 1996·Journal of Peptide Science : an Official Publication of the European Peptide Society·A TuziO Pieroni
Jan 1, 1993·Progress in Biophysics and Molecular Biology·A A Rashin
Aug 1, 1996·International Journal of Biological Macromolecules·S N MitraT P Singh
Sep 21, 1994·Biochimica Et Biophysica Acta·P FábiánS Pongor
Jun 5, 2008·Journal of Peptide Science : an Official Publication of the European Peptide Society·R LatajkaP Kafarski
Feb 3, 2015·Journal of Peptide Science : an Official Publication of the European Peptide Society·Marco CrismaClaudio Toniolo
Dec 1, 1991·International Journal of Peptide and Protein Research·M R CiajoloO Pieroni
Aug 1, 1996·International Journal of Peptide and Protein Research·S DeyT P Singh
Mar 1, 1992·International Journal of Peptide and Protein Research·V S Chauhan, K K Bhandary
Oct 12, 1999·The Journal of Peptide Research : Official Journal of the American Peptide Society·S BhatiaT P Singh
Sep 4, 1998·The Journal of Peptide Research : Official Journal of the American Peptide Society·R VijayaraghavanT P Singh
Dec 1, 1995·International Journal of Peptide and Protein Research·K R RajashankarS Ramakumar
Jan 1, 1996·Progress in Biophysics and Molecular Biology·T P Singh, P Kaur

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