Influence of amino acid sequence on the interaction of short peptides containing 3-[2-(9-anthryl)benzoxazol-5-yl]-alanine with β-cyclodextrin

• Authors: Justyna Mrozek , Katarzyna Guzow , Emilia Sikorska , Wiesław Wiczk
• Languages of publication: EN

Abstracts

EN

The influence of peptide sequence and Leu chirality in linear and cyclic peptides containing 3-[2-(9-anthryl)benzoxazol-5-yl]alanine on interaction with β-cyclodextrin were studied using fluorescence and NMR spectroscopy. The analysis of enthalpy-entropy compensation effect (α=1.05±0.02 and TΔS00=15.1±0.5 kJ mol−1) indicates that the entropic contribution connected with the solvent reorganization is the major factor governing the peptides-β-cyclodextrin complexation. Moreover, spatial orientation of guest-host molecule depends more than association constant on Leu residue configuration. However, the cyclization of the peptide chain substantially decrease the association constant with β-CD. An analysis of 2D NMR spectra reveals that inclusion complex is formed by penetration of cyclodextrin cavity from wider and narrow rims by anthryl group in the case of Box(Ant)-SPKL or anthryl and Leu residues for Box(Ant)-SPK(D)L analogue. [...]

Keywords

EN

Cyclodextrin; Peptides; Fluorescence spectroscopy; NMR spectroscopy; Inclusion complex

• Publisher: De Gruyter Open
• Journal: Open Chemistry
• Year: 2011
• Volume: 9
• Issue: 6
• Pages: 1046-1055

Dates

published

1 - 12 - 2011

online

27 - 9 - 2011

Contributors

author

Justyna Mrozek

• Faculty of Chemistry, University of Gdańsk, 80-952, Gdańsk, Poland

author

Katarzyna Guzow

• Faculty of Chemistry, University of Gdańsk, 80-952, Gdańsk, Poland

author

Emilia Sikorska

• Faculty of Chemistry, University of Gdańsk, 80-952, Gdańsk, Poland

author

Wiesław Wiczk

• Faculty of Chemistry, University of Gdańsk, 80-952, Gdańsk, Poland

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Identifiers

DOI

10.2478/s11532-011-0103-x