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Amino Acids

, Volume 47, Issue 10, pp 2215–2227 | Cite as

Investigating the inclusion properties of aromatic amino acids complexing beta-cyclodextrins in model peptides

  • Jolanda Valentina Caso
  • Luigi Russo
  • Maddalena Palmieri
  • Gaetano Malgieri
  • Stefania Galdiero
  • Annarita Falanga
  • Carla Isernia
  • Rosa IacovinoEmail author
Original Article

Abstract

Cyclodextrins are commonly used as complexing agents in biological, pharmaceutical, and industrial applications since they have an effect on protein thermal and proteolytic stability, refolding yields, solubility, and taste masking. β-cyclodextrins (β-CD), because of their cavity size are a perfectly suited complexing agent for many common guest moieties. In the case of peptide-cyclodextrin and protein-cyclodextrin host–guest complexes the aromatic amino acids are reported to be the principal responsible of the interaction. For these reasons, we have investigated the inclusion properties of nine designed tripeptides, obtained permuting the position of two l-alanines (Ala, A) with that of one l-tryptophan (Trp, W), l-phenylalanine (Phe, F), or l-tyrosine (Tyr, Y), respectively. Interestingly, the position of the aromatic side-chain in the sequence appears to modulate the β-CD:peptide binding constants, determined via UV–Vis and NMR spectroscopy, which in turn assumes values higher than those reported for the single amino acid. The tripeptides containing a tyrosine showed the highest binding constants, with the central position in the Ac-AYA-NH2 peptide becoming the most favorite for the interaction. A combined NMR and Molecular Docking approach permitted to build detailed complex models, highlighting the stabilizing interactions of the neighboring amino acids backbone atoms with the upper rim of the β-CD.

Keywords

Inclusion complex β-Cyclodextrin Aromatic amino acids UV–Vis spectroscopy NMR Molecular docking 

Notes

Acknowledgments

The authors are grateful to Cristina Di Donato for useful discussion. This work was partially funded by M.I.U.R. Grants PRIN 2010 (to Roberto Fattorusso).

Conflict of interest

The authors declare that there are no conflicts of interest.

Supplementary material

726_2015_2003_MOESM1_ESM.docx (22 kb)
Supplementary material 1 (DOCX 21 kb)

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Copyright information

© Springer-Verlag Wien 2015

Authors and Affiliations

  • Jolanda Valentina Caso
    • 1
  • Luigi Russo
    • 1
  • Maddalena Palmieri
    • 1
  • Gaetano Malgieri
    • 1
  • Stefania Galdiero
    • 2
  • Annarita Falanga
    • 2
  • Carla Isernia
    • 1
  • Rosa Iacovino
    • 1
    Email author
  1. 1.Department of Environmental, Biological and Pharmaceutical Sciences and TechnologiesSecond University of NaplesCasertaItaly
  2. 2.Department of PharmacyUniversity of Naples Federico IINaplesItaly

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