VCD studies on cyclic peptides assembled from L-α-amino acids and a trans-2-aminocyclopentane- or trans-2-aminocyclohexane carboxylic acid

E. Vass, U. Strijowski, K. Wollschläger, I. Mándity, G. Szilvágyi, M. Jewgiński, K. Gaus, S. Royo, Zs. Majer, N. Sewald, M. Hollósi

Research output: Contribution to journalArticle

8 Citations (Scopus)

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.

Original languageEnglish
Pages (from-to)613-620
Number of pages8
JournalJournal of Peptide Science
Volume16
Issue number11
DOIs
Publication statusPublished - Nov 2010

Fingerprint

Cyclic Peptides
Circular Dichroism
Carboxylic Acids
Amino Acids
Nuclear magnetic resonance
Circular dichroism spectroscopy
Peptidomimetics
Vibrational spectroscopy
Density functional theory
Conformations
peptide L
Spectrum Analysis
Experiments

Keywords

  • Cyclic peptides
  • Electronic circular dichroism
  • NMR
  • trans-2-aminocyclohexane carboxylic acid
  • trans-2-aminocyclopentane carboxylic acid
  • Vibrational circular dichroism

ASJC Scopus subject areas

  • Structural Biology
  • Molecular Medicine
  • Molecular Biology
  • Biochemistry
  • Pharmacology
  • Drug Discovery
  • Organic Chemistry

Cite this

VCD studies on cyclic peptides assembled from L-α-amino acids and a trans-2-aminocyclopentane- or trans-2-aminocyclohexane carboxylic acid. / Vass, E.; Strijowski, U.; Wollschläger, K.; Mándity, I.; Szilvágyi, G.; Jewgiński, M.; Gaus, K.; Royo, S.; Majer, Zs.; Sewald, N.; Hollósi, M.

In: Journal of Peptide Science, Vol. 16, No. 11, 11.2010, p. 613-620.

Research output: Contribution to journalArticle

Vass, E. ; Strijowski, U. ; Wollschläger, K. ; Mándity, I. ; Szilvágyi, G. ; Jewgiński, M. ; Gaus, K. ; Royo, S. ; Majer, Zs. ; Sewald, N. ; Hollósi, M. / VCD studies on cyclic peptides assembled from L-α-amino acids and a trans-2-aminocyclopentane- or trans-2-aminocyclohexane carboxylic acid. In: Journal of Peptide Science. 2010 ; Vol. 16, No. 11. pp. 613-620.
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