Design of specific structures using alpha,beta-dehydro-phenylalanine residues: synthesis, crystal structure, and molecular conformation of Boc-L-Val-delta Phe-delta Phe-L-Val-delta Phe-delta Phe-L-Val-OCH3, a 3(10)-helical heptapeptide

Biopolymers
S N MitraT P Singh

Abstract

The peptide design using alpha,beta-dehydro-residues has wide applications. To design an extensive 3(10)-helical conformation, a heptapeptide Boc-L-Val-delta Phe-delta Phe-L-Val-delta Phe-delta Phe-L-Val-OCH3, with a repeat of two consecutive delta Phe residues has been synthesized using an azlactone method in solution phase. This is the first design using a repeat of two consecutive delta Phe residues. It is observed that the delta Phe in a sequence of two consecutive delta Phe residues, adopts only one set of phi, psi values, i.e., +/- 60 degrees, +/- 30 degrees, thus making it a specific design tool. The peptide crystallized from its solution in a methanol-water mixture in the space group P2(1) with a = 10.159(5)A, b = 20.057(2)A, c = 14.448(3)A, beta = 99.41(2)degrees, V = 2904(2)A3. The structure has been determined by direct methods and refined to an R value of 0.048 for 5404 observed [I > or = 3 sigma(I)] reflections. The structure consists of a heptapeptide Boc-L-Val-delta Phe-delta Phe-L-Val-delta Phe-delta Phe-L-Val-OCH3 and a solvent methanol molecule in the asymmetric unit. All peptide units in the structure are trans. As a result of six overlapping type III beta-turns formed involving seven residues and five intram...Continue Reading

References

Nov 12, 1975·Journal of the American Chemical Society·O PieroniF Ciardelli
Nov 1, 1991·International Journal of Peptide and Protein Research·S DeyT P Singh
Oct 15, 1991·Biopolymers·K V SomanD A Case
Dec 1, 1991·International Journal of Peptide and Protein Research·M R CiajoloO Pieroni
Aug 1, 1990·Acta Crystallographica. Section B, Structural Science·T P SinghH C Patel
Jan 1, 1990·Proceedings of the National Academy of Sciences of the United States of America·G R MarshallM T Leplawy
Aug 1, 1980·International Journal of Peptide and Protein Research·E BenedettiH A Scheraga

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Citations

Feb 3, 2015·Journal of Peptide Science : an Official Publication of the European Peptide Society·Marco CrismaClaudio Toniolo
Oct 17, 1998·The Journal of Peptide Research : Official Journal of the American Peptide Society·U A RamagopalV S Chauhan
Oct 12, 1999·The Journal of Peptide Research : Official Journal of the American Peptide Society·S BhatiaT P Singh

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