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

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Macedowska A., Siodlak D., Rzeszotarska B.

Acta Biochimica Polonica

2006

tom 53

nr 1

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.

Ograniczanie wyników

1 Acta Biochimica Polonica

1 Macedowska A.

1 Rzeszotarska B.

1 Siodlak D.

1 2006

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