Selective α-glucosylation of eugenol by α-glucosyl transfer enzyme of Xanthomonas campestris WU-9701

Toshiyuki Sato, Hiroaki Takeuchi, Kei Takahashi, Jun Kurosu, Keishiro Yoshida, Takanori Tsugane, Susumu Shimura, Kuniki Kino, Kotaro Kirimura

    Research output: Contribution to journalArticle

    12 Citations (Scopus)

    Abstract

    For one-step enzymatic synthesis of eugenyl α-glucoside as a promising pro-drug for a hair restorer and a derivative of spices, selective α-glucosylation of eugenol was carried out using the α-glucosyl transfer enzyme of Xanthomonas campestris WU-9701. When 130 μmol eugenol and crude enzyme showing 1.0 unit of α-glucosyl transfer activity were shaken in 2 ml of 10 mM H3BO3-NaOH-KCl buffer (pH 8.0) containing 1.2 M maltose as a glucosyl donor at 40°C, only one form of eugenyl glucoside was selectively obtained as a product and identified as eugenyl α-D-glucopyranoside (α-EG) by 13C-NMR, 1H-NMR, and two-dimensional heteronuclear multiple-bond coherence analyses. In the reaction, no other glucosylated products such as maltotriose or eugenyl maltoside were detected in the reaction mixture. The reaction at 40°C for 48 h under the above conditions yielded 68 μmol α-EG in 2 ml suspension, and the maximum molar conversion yield based on the amount of eugenol supplied reached 52%.

    Original languageEnglish
    Pages (from-to)199-202
    Number of pages4
    JournalJournal of Bioscience and Bioengineering
    Volume96
    Issue number2
    DOIs
    Publication statusPublished - 2003

    Fingerprint

    Xanthomonas campestris
    Eugenol
    Enzymes
    Glucosides
    Nuclear magnetic resonance
    Maltose
    Spices
    Prodrugs
    Derivatives
    Suspensions
    Buffers

    Keywords

    • Eugenol
    • Pro-drug
    • Selective α-glucosylation
    • Transglucosylation
    • Xanthomonas campestris

    ASJC Scopus subject areas

    • Biotechnology
    • Bioengineering

    Cite this

    Selective α-glucosylation of eugenol by α-glucosyl transfer enzyme of Xanthomonas campestris WU-9701. / Sato, Toshiyuki; Takeuchi, Hiroaki; Takahashi, Kei; Kurosu, Jun; Yoshida, Keishiro; Tsugane, Takanori; Shimura, Susumu; Kino, Kuniki; Kirimura, Kotaro.

    In: Journal of Bioscience and Bioengineering, Vol. 96, No. 2, 2003, p. 199-202.

    Research output: Contribution to journalArticle

    Sato, Toshiyuki ; Takeuchi, Hiroaki ; Takahashi, Kei ; Kurosu, Jun ; Yoshida, Keishiro ; Tsugane, Takanori ; Shimura, Susumu ; Kino, Kuniki ; Kirimura, Kotaro. / Selective α-glucosylation of eugenol by α-glucosyl transfer enzyme of Xanthomonas campestris WU-9701. In: Journal of Bioscience and Bioengineering. 2003 ; Vol. 96, No. 2. pp. 199-202.
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