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Synthetic and conformational studies on dehydrophenylalanine containing model peptides

Kaur, Paramjeet and Uma, K and Balaram, P and Chauhan, VS (1989) Synthetic and conformational studies on dehydrophenylalanine containing model peptides. In: International Journal of Peptide & Protein Research, 33 (2). 103 -109 .

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Official URL: http://onlinelibrary.wiley.com/doi/10.1111/j.1399-...

Abstract

Four model dipeptides containing a Z-dehydrophenylalanine residue (ΔZPhe) at the C-terminal, Boc-X-ΔZ Phe-NHMe (X = Ala (1), Gly (2), Pro (3), and Val (4)), have been synthesised and their solution conformations investigated by 270 MHz 1H n.m.r. and i.r. spectroscopy. N.m.r. studies on these peptides clearly show the presence of intramolecularly hydrogen bonded structures in CHCl3 solutions while such structures appear to be absent in the corresponding saturated peptides. This conclusion is also supported by i.r. studies. Studies of the nuclear Overhauser effect provided evidence for the occurrence of a significant population of β-turn structures in solvents like CDCl3 and (CD3)2SO. The observed NOES are consistent with a major contribution from Type II β-turn structure in CDCl3, while in (CD3)2SO solutions there is evidence of a partially extended structure also.

Item Type: Journal Article
Additional Information: Copyright of this article belongs to John Wiley & Sons.
Keywords: β-turn;dehydrophenylalanine;nuclear Overhauser effects.
Department/Centre: Division of Biological Sciences > Molecular Biophysics Unit
Date Deposited: 20 Oct 2010 05:43
Last Modified: 20 Oct 2010 05:43
URI: http://eprints.iisc.ernet.in/id/eprint/33309

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