Conformational properties of N-acetyl-N-methyl-alpha,beta-dehydroalanine N'-methylamide.

Agnieszka Macedowska; Dawid Siodłak; Barbara Rzeszotarska

doi:10.18388/abp.2006_3382

Conformational properties of N-acetyl-N-methyl-alpha,beta-dehydroalanine N'-methylamide.

Agnieszka Macedowska Institute of Chemistry, University of Opole, Opole, Poland.;
Dawid Siodłak
Barbara Rzeszotarska

DOI: https://doi.org/10.18388/abp.2006_3382

Abstract

The conformational properties of Ac-Delta(Me)Ala-NHMe (N-acetyl-N-methyl-alpha,beta-dehydroalanine N'-methylamide), as the simplest model of N-methyl-alpha,beta-dehydroamino acids, was examined with theoretical methods and in comparison with Ac-DeltaAla-NHMe and Ac-DeltaAla-NMe(2). The N-terminal amide of the Delta(Me)Ala residue easily adopts the configuration cis and the torsion angles phi, psi are highly flexible. The Delta(Me)Ala residue is a conformational flexibilizer as compared to the parent DeltaAla, which is a conformational stiffener. This seems to be the reason why Delta(Me)Ala is found in small natural cyclic peptides, where it ensures the conformational flexibility necessary for biological action.

Published

2006-03-09

Issue

Vol. 53 No. 1 (2006)

Section

Articles

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