Conformational properties of N-acetyl-N-methyl-α,β-dehydroalanine N'-methylamide

• Authors: Agnieszka Macedowska , Dawid Siodłak , Barbara Rzeszotarska
• Languages of publication: EN

Abstracts

EN

The conformational properties of Ac-Δ(Me)Ala-NHMe (N-acetyl-N-methyl-α,β-dehydroalanine N'-methylamide), as the simplest model of N-methyl-α,β-dehydroamino acids, was examined with theoretical methods and in comparison with Ac-ΔAla-NHMe and Ac-ΔAla-NMe2. The N-terminal amide of the Δ(Me)Ala residue easily adopts the configuration cis and the torsion angles φ, ψ are highly flexible. The Δ(Me)Ala residue is a conformational flexibilizer as compared to the parent ΔAla, which is a conformational stiffener. This seems to be the reason why Δ(Me)Ala is found in small natural cyclic peptides, where it ensures the conformational flexibility necessary for biological action.

Keywords

EN

ab initio/DFT calculations; N-alkylpeptides; cis-trans isomerisation; α,β-dehydroamino acids; peptide design

• Publisher: Polish Biochemical Society
• Journal: Acta Biochimica Polonica
• Year: 2006
• Volume: 53
• Issue: 1
• Pages: 227-232

Dates

published

2006

received

2005-11-06

revised

2006-02-12

accepted

2006-03-02

(unknown)

2006-03-09

Contributors

author

Agnieszka Macedowska

• Institute of Chemistry, University of Opole, Opole, Poland

author

Dawid Siodłak

• Institute of Chemistry, University of Opole, Opole, Poland

author

Barbara Rzeszotarska

• Institute of Chemistry, University of Opole, Opole, Poland

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