Extraction behavior of amino acids by calix[6]arene carboxylic acid derivatives

Tatsuya Oshima, Masahiro Goto, Shintaro Furusaki

    Research output: Contribution to journalArticlepeer-review

    50 Citations (Scopus)

    Abstract

    A series of calixarene carboxylic acid derivatives were synthesized for the extraction of amino acids. A calix[6]arene carboxylic acid derivative showed the highest extractability to the target tryptophan ester. The main driving force for the complexation was the interaction between the ammonium cation of the amino acid and the oxygen atoms of the host molecule. Stripping of amino acids was also accomplished by contacting the organic solution with a fresh acidic solution. Based on slope and Job method analyses, it was confirmed that the calix[6]arene forms a 1:1 complex with the amino acid ester. The structure of the complex between the calix[6]arene and the amino acid was investigated by 1H-NMR and CD spectra. The calix[6]arene includes a guest molecule in the cavity, and the inclusion induces the asymmetrization of the host molecule. This host compound functions as a novel recognition tool for amino acids.

    Original languageEnglish
    Pages (from-to)77-86
    Number of pages10
    JournalJournal of Inclusion Phenomena
    Volume43
    Issue number1-2
    DOIs
    Publication statusPublished - 2002

    All Science Journal Classification (ASJC) codes

    • Food Science
    • Chemistry(all)
    • Condensed Matter Physics

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