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

研究成果: Article査読

123 被引用数 (Scopus)

抄録

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.

本文言語English
ページ(範囲)1487-1493
ページ数7
ジャーナルJournal of Organic Chemistry
64
5
DOI
出版ステータスPublished - 1999 3 5
外部発表はい

ASJC Scopus subject areas

  • 有機化学

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