Construction of α-helix peptides with β-cyclodextrin and dansyl units and their conformational and molecular sensing properties

Sachiko Matsumura, Seiji Sakamoto, Akihiko Ueno, Hisakazu Mihara

Research output: Contribution to journalArticle

69 Citations (Scopus)

Abstract

In order to apply de novo peptide design to molecular sensing, we designed and synthesized α-helical peptides with β-cyclodextrin (β-CDx) as a binding site and a dansyl unit (Dns) as a fluorescence sensing site. The conformational and molecular sensing properties of the peptides with β-CDx and Dns in various positions were investigated. Circular dichroism and fluorescence measurements revealed that β-CDx and Dns form intramolecular complexes which depend on their positions in the peptides. In the 17 residual peptides named EK3 and EK3R, in which β-CDx and Dns were introduced at the fourth and the eighth positions (EK3) or at the eighth and the fourth positions (EK3R), Dns was deeply included in the CDx cavity and formed a more stable self-inclusion complex with CDx than in the peptides EK6 and EK6R, in which these moieties were at the eighth and the fifteenth positions or at the fifteenth and the eighth positions, respectively. The stability of the self-inclusion complex between β-CDx and Dns controlled the α-helix structure as well as the binding and sensing abilities for the exogenous guests. These results demonstrate the usefulness of peptide tertiary structure for arranging CDx and other functional units, and suggest that this approach is important in the development of a new type of CDx-based sensory system.

Original languageEnglish
Pages (from-to)1781-1788
Number of pages8
JournalChemistry - A European Journal
Volume6
Issue number10
DOIs
Publication statusPublished - 2000 May 15

Keywords

  • Cyclodextrins
  • Helical structures
  • Inclusion compounds
  • Molecular recognition
  • Peptides

ASJC Scopus subject areas

  • Catalysis
  • Organic Chemistry

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