VCD studies on cyclic peptides assembled from L-α-amino acids and a trans-2-aminocyclopentane- or trans-2-aminocyclohexane carboxylic acid.
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.
Vass
E
E
Institute of Chemistry, Eötvös Loránd University, 1117 Budapest, Pázmány Péter sétány 1/a, Hungary.
Strijowski
U
U
Wollschläger
K
K
Mándity
I M
IM
Szilvágyi
G
G
Jewgiński
M
M
Gaus
K
K
Royo
S
S
Majer
Z
Z
Sewald
N
N
Hollósi
M
M
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
D003509:Cyclohexanecarboxylic Acids; D003514:Cyclohexylamines; D010456:Peptides, Cyclic; D057786:Peptidomimetics; D003515:Cycloleucine; C065594:cispentacin; C103271:2-aminocyclohexanecarboxylic acid