Molecular recognition study on supramolecular systems. 20. Molecular recognition and enantioselectivity of aliphatic alcohols by L-tryptophan- modified β-cyclodextrin

Yu Liu, Bao Hang Han, Shi Xin Sun, Takehiko Wada, Yoshihisa Inoue

Research output: Contribution to journalArticlepeer-review

121 Citations (Scopus)

Abstract

L-Tryptophan-modified β-cyclodextrin (L-Trp-β-CD) has been synthesized and its molecular recognition behavior investigated through fluorescence and circular dichroism spectrometry, as well as fluorescence lifetime measurement in the presence and absence of various alcohols as guest molecules. Employing the indolyl group as a spectral probe, spectrofluorometric and spectropolarimetric titrations have been performed in aqueous phosphate buffer solution at pH 7.20 to calculate the complex stability constants for 1:1 inclusion complexation of L-Trp-β-CD with several series of alcohols at 25 °C. The results obtained indicate that L-Trp-β-CD can recognize not only size/shape and hydrophobicity but also the enantiomeric and geometrical isomers of the guest alcohols, showing a 230-fold molecular selectivity (13.5 kJ mol-1) for 2-adamantanol over cyclopentanol among the cyclic alcohols examined. Moderate enantiomeric selectivities of 1.2 and 1.9 for (-)-isomers of borneol and menthol, respectively, and geometrical selectivity of 2.0 for geraniol over nerol have also been observed.

Original languageEnglish
Pages (from-to)1487-1493
Number of pages7
JournalJournal of Organic Chemistry
Volume64
Issue number5
DOIs
Publication statusPublished - 1999 Mar 5
Externally publishedYes

ASJC Scopus subject areas

  • Organic Chemistry

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