Conformational investigation of α,β-dehydropeptides. XIII. Conformational properties of N-acetyl-α,β-dehydrovaline N',N'-dimethylamide.

• Authors: Dawid Siodłak , Barbara Rzeszotarska , Małgorzata A Broda , Anna E Kozioł , Edyta Kołodziejczyk
• Languages of publication: EN

Abstracts

EN

The crystal structure of Ac-ΔVal-NMe2 (ΔVal = α,β-dehydrovaline) was determined by X-ray crystallography. The found angles φ = -60° and ψ = 125° correspond exactly to the respective values of the (i + 1)th residue in idealised β-turn II/VIa. Ab initio/DFT studies revealed that the molecule adopts the angle ψ restricted only to about |130°| and very readily attains the angle φ = about -50°. This is in line with its solid-state conformation. Taken together, these data suggest that the ΔVal residue combined with a C-terminal tertiary amide is a good candidate at the (i + 1)th position in a type II/VIa β-turn.

Keywords

EN

ab initio/DFT calculations; N',N'-dimethylamides; X-ray crystallography; α,β-dehydroamino acids; peptide design; valine derivative

• Publisher: Polish Biochemical Society
• Journal: Acta Biochimica Polonica
• Year: 2004
• Volume: 51
• Issue: 1
• Pages: 145-152

Dates

published

2004

received

2003-10-31

revised

2004-02-17

accepted

2004-03-08

Contributors

author

Dawid Siodłak

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

author

Barbara Rzeszotarska

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

author

Małgorzata A Broda

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

author

Anna E Kozioł

• Faculty of Chemistry, Maria Curie-Skłodowska University, Lublin, Poland

author

Edyta Kołodziejczyk

• nstitute of Physical Chemistry, Polish Academy of Sciences, Warszawa, Poland

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