Guest-induced conformational change of β-cyclodextrin capped with an environmentally sensitive chromophore

Kahee Fujita, Tadashi Ueda, Taiji Imoto, Iwao Tabushi, Namiko Toh, Toshitaka Koga

Research output: Contribution to journalArticle

42 Citations (Scopus)

Abstract

A capped cyclodextrin, 6-deoxy-6-(p-hydroxy-m-nitrophenacylthio)-β-cyclodextrin, was prepared in order to detect any conformational change of the host upon the guest binding. The association constant between the cyclodextrin and 1-adamantanecarboxylate, cyclohexanecarboxylate, p-methylbenzoate, 3,3-dimethylbutyrate, or 2,2-dimethylpropionate was enhanced 20, 5.3, 3.7, 2.3, or 2.0 times, respectively, by chromophore capping. The changes in the electronic, NMR, and circular dichroism spectra as well as pKa of this cyclodextrin upon binding of the guest strongly indicate a conformational change around the chromophoric moiety of the cyclodextrin.

Original languageEnglish
Pages (from-to)72-84
Number of pages13
JournalBioorganic Chemistry
Volume11
Issue number1
DOIs
Publication statusPublished - Mar 1982

All Science Journal Classification (ASJC) codes

  • Biochemistry
  • Molecular Biology
  • Drug Discovery
  • Organic Chemistry

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