title: VCD studies on cyclic peptides assembled from L-α-amino acids and a trans-2-aminocyclopentane- or trans-2-aminocyclohexane carboxylic acid.
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.
authors.affiliation: Institute of Chemistry, Eötvös Loránd University, 1117 Budapest, Pázmány Péter sétány 1/a, Hungary.
authors.forename: E
authors.initials: E
authors.lastname: Vass
authors.forename: U
authors.initials: U
authors.lastname: Strijowski
authors.forename: K
authors.initials: K
authors.lastname: Wollschläger
authors.forename: I M
authors.initials: IM
authors.lastname: Mándity
authors.forename: G
authors.initials: G
authors.lastname: Szilvágyi
authors.forename: M
authors.initials: M
authors.lastname: Jewgiński
authors.forename: K
authors.initials: K
authors.lastname: Gaus
authors.forename: S
authors.initials: S
authors.lastname: Royo
authors.forename: Z
authors.initials: Z
authors.lastname: Majer
authors.forename: N
authors.initials: N
authors.lastname: Sewald
authors.forename: M
authors.initials: M
authors.lastname: Hollósi
mesh_terms: D002942:Circular Dichroism / Q000379:methods; D003509:Cyclohexanecarboxylic Acids / Q000737:chemistry*; D003514:Cyclohexylamines / Q000737:chemistry*; D003515:Cycloleucine / Q000031:analogs & derivatives / Q000737:chemistry; D008968:Molecular Conformation; D056004:Molecular Dynamics Simulation; D019906:Nuclear Magnetic Resonance, Biomolecular; D010456:Peptides, Cyclic / Q000737:chemistry*; D057786:Peptidomimetics
chemical_list: D003509:Cyclohexanecarboxylic Acids; D003514:Cyclohexylamines; D010456:Peptides, Cyclic; D057786:Peptidomimetics; D003515:Cycloleucine; C065594:cispentacin; C103271:2-aminocyclohexanecarboxylic acid