Thermodynamical and geometrical characterization of molecular recognition by cage-type and peptide azapara-cyclophanes in aqueous media

Yukito Murakami, Osamu Hayashida, Kazuya Ono, Yoshio Hisaeda

Research output: Contribution to journalArticle

14 Citations (Scopus)

Abstract

A cage-type cyclophane which is constructed with two rigid macrocyclic skeletons, tetraaza[6.1.6.1]paracyclophane and tetraaza[3.3.3.3]paracyclophane, and four chiral bridging components strongly binds anionic and hydrophobic guests, such as 8-anilinonaphthalene-1-sulfonate and 6-p-toluidinonaphthalene-2-sulfonate. Thermodynamic parameters were evaluated from temperature-dependent complexation constants for the cage-type host and a peptide cyclophane, which was prepared by introducing four valine residues into a tetraaza[6.1.6.1]-paracyclophane skeleton, with the hydrophobic guests as determined by fluorescence spectroscopy. The complexation of the former and latter hosts with the guests gave positive and negative AS values, respectively. The positive AS values come primarily from effective desolvation of the guest molecule incorporated into the hydrophobic host cavity and partly from conformational changes around the bridging moieties of the cage-type host upon complexation, as evidenced by fluorescence polarization and circular dichroism measurements. The geometrical arrangements of the guest molecules in the respective inclusion complexes were clarified by detailed 1H NMR analysis.

Original languageEnglish
Pages (from-to)2319-2324
Number of pages6
JournalPure and Applied Chemistry
Volume65
Issue number11
DOIs
Publication statusPublished - Jan 1 1993

All Science Journal Classification (ASJC) codes

  • Chemistry(all)
  • Chemical Engineering(all)

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