Influence of solvents on conformation of dehydropeptides

► Influence of a solvent polarity on the conformation of dehydropeptides was examined. ► Molecular conformation was determined by DFT and molecular dynamic methods. ► Increasing of the solvent polarity promote ordered conformation of peptide. ► Tetrapeptide and hexapeptide adopt β-turn conformation...

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Bibliographic Details
Published in:Journal of molecular structure 2013-03, Vol.1035, p.129-139
Main Authors: Jewginski, Michal, Latajka, Rafal, Krezel, Artur, Haremza, Kinga, Makowski, Maciej, Kafarski, Pawel
Format: Article
Language:English
Subjects:
amino acids
Circular dichroism
Dehydropeptide
Dehydropeptide conformation
Dehydrophenylalanine
hydrogen bonding
NMR
nuclear magnetic resonance spectroscopy
Solvent polarity
solvents
temperature
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Summary:► Influence of a solvent polarity on the conformation of dehydropeptides was examined. ► Molecular conformation was determined by DFT and molecular dynamic methods. ► Increasing of the solvent polarity promote ordered conformation of peptide. ► Tetrapeptide and hexapeptide adopt β-turn conformation in more polar solvent. Structural investigations of dehydropeptides containing (Z)-dehydrophenylalanine in solvents characterized by different polarity are discussed. The conformational analysis are based on spectroscopic methods (NMR, CD), molecular modeling techniques and in case of the tripeptide, ab initio methods. The results of temperature experiment indicate, that the only conformation of the investigated hexapeptide 3 is stabilized by intramolecular hydrogen bonds. Depending on the length of the peptide chain, the polarity of solvent influences on arrangement of the side chain of the amino acids or of the main chain of the peptide.
ISSN:0022-2860
1872-8014
DOI:10.1016/j.molstruc.2012.08.042