|
|||||
|
|
VCD studies on cyclic peptides assembled from L‐α‐amino acids and a trans‐2‐aminocyclopentane‐ or trans‐2‐aminocyclohexane carboxylic acid |
|
| Authors: | E Vass U Strijowski K Wollschläger I M Mándity G Szilvágyi M Jewgiński K Gaus S Royo Z Majer N Sewald M Hollósi |
| Institution: | 1. Institute of Chemistry, E?tv?s Loránd University, 1117 Budapest, Pázmány Péter sétány 1/a, Hungary;2. Organic and Bioorganic Chemistry, Department of Chemistry, Bielefeld University, Universit?tsstrasse 25, 33615 Bielefeld, Germany;3. Institutes of Pharmaceutical Chemistry and Medical Chemistry, University of Szeged, E?tv?s u. 6, 6720 Szeged, Hungary;4. Institute of Chemistry, University of Opole, Oleska 48, Opole 45‐052, Poland;5. Department of Bioorganic Chemistry, Wroc?aw University of Technology, Wybrzeze Wyspianskiego 27, 50‐370 Wroc?aw, Poland |
| Abstract: | The increasing interest in peptidomimetics of biological relevance prompted us to synthesize a series of cyclic peptides comprising trans‐2‐aminocyclohexane carboxylic acid (Achc) or trans‐2‐aminocyclopentane carboxylic acid (Acpc). NMR experiments in combination with MD calculations were performed to investigate the three‐dimensional structure of the cyclic peptides. These data were compared to the conformational information obtained by electronic circular dichroism (ECD) and vibrational circular dichroism (VCD) spectroscopy. Experimental VCD spectra were compared to theoretical VCD spectra computed quantum chemically at B3LYP/6‐31G(d) density functional theory (DFT) level. The good agreement between the structural features derived from the VCD spectra and the NMR‐based structures underlines the applicability of VCD in studying the conformation of small cyclic peptides. Copyright © 2010 European Peptide Society and John Wiley & Sons, Ltd. |
| Keywords: | vibrational circular dichroism electronic circular dichroism trans‐2‐aminocyclohexane carboxylic acid trans‐2‐aminocyclopentane carboxylic acid cyclic peptides NMR |