Conformational investigation of alpha,beta-dehydropeptides. XIII. Conformational properties of N-acetyl-alpha,beta-dehydrovaline N',N'-dimethylamide.

Dawid Siodłak; Barbara Rzeszotarska; Małgorzata A Broda; Anna E Kozioł; Edyta Kołodziejczyk

doi:10.18388/abp.2004_3606

Conformational investigation of alpha,beta-dehydropeptides. XIII. Conformational properties of N-acetyl-alpha,beta-dehydrovaline N',N'-dimethylamide.

Dawid Siodłak Institute of Chemistry, University of Opole, Opole, Poland.;
Barbara Rzeszotarska
Małgorzata A Broda
Anna E Kozioł
Edyta Kołodziejczyk

DOI: https://doi.org/10.18388/abp.2004_3606

Abstract

The crystal structure of Ac-DeltaVal-NMe(2) (DeltaVal = alpha,beta-dehydrovaline) was determined by X-ray crystallography. The found angles phi = -60 degrees and psi = 125 degrees correspond exactly to the respective values of the (i + 1)th residue in idealised beta-turn II/VIa. Ab initio/DFT studies revealed that the molecule adopts the angle psi restricted only to about |130 degrees | and very readily attains the angle phi = about -50 degrees. This is in line with its solid-state conformation. Taken together, these data suggest that the DeltaVal residue combined with a C-terminal tertiary amide is a good candidate at the (i + 1)th position in a type II/VIa beta-turn.

Published

2004-03-31

Issue

Vol. 51 No. 1 (2004)

Section

Articles

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