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

100%

Macedowska A., Siodłak D., Rzeszotarska B.

2006

vol. 53

issue 1

227-232

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.

Conformational properties of N-acetyl-L-alanine N',N'-dimethylamide.

86%

Siodłak D., Rzeszotarska B., Broda M. A.

vol. 51

issue 1

137-143

Ab initio/DFT analysis of the conformational properties of free Ac-Ala-NMe2 (N-acetyl-L-alanine-N',N'-dimethylamide) in terms of the N-H···O, N-H···N, C-H···O hydrogen bonds and Cδ+ = Oδ- dipole attractions was performed. The Ala residue combined with the C-terminal tertiary amide prefers an extended conformation and that characteristic of the (i + 1)th position of the βVIb turn. These can be easily remodelled into a structure compatible with the (i + 1)th position of the βII/βVIa turn. The residue has also the potential to adopt the conformation accommodated at both central positions of the βIII/βIII' turn or the (i + 1)th position of the βI/β'I turn.

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2 Acta Biochimica Polonica

1 2006

1 2004

2 Rzeszotarska B.

2 Siodłak D.

1 Broda M. A.

1 Macedowska A.

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

Conformational properties of N-acetyl-L-alanine N',N'-dimethylamide.