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

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Central European Journal of Chemistry

Abstract

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 TΔS0 0=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.

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Authors and Affiliations

  1. Faculty of Chemistry, University of Gdańsk, 80-952, Gdańsk, Poland

    Justyna Mrozek, Katarzyna Guzow, Emilia Sikorska & Wiesław Wiczk

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  1. Justyna Mrozek
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  2. Katarzyna Guzow
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  3. Emilia Sikorska
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  4. Wiesław Wiczk
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Correspondence to Wiesław Wiczk.

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Mrozek, J., Guzow, K., Sikorska, E. et al. Influence of amino acid sequence on the interaction of short peptides containing 3-[2-(9-anthryl)benzoxazol-5-yl]-alanine with β-cyclodextrin. cent.eur.j.chem. 9, 1046–1055 (2011). https://doi.org/10.2478/s11532-011-0103-x

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  • DOI: https://doi.org/10.2478/s11532-011-0103-x

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