Enzymatic carboxylation of hydroxystilbenes by the γ-resorcylic acid decarboxylase from Rhizobium radiobacter WU-0108 under reverse reaction conditions

Masaru Sato, Nozomu Sakurai, Hideyuki Suzuki, Daisuke Shibata, Kuniki Kino

    Research output: Contribution to journalArticle

    6 Citations (Scopus)

    Abstract

    We examined 66 aromatics for carboxylation by the γ-resorcylic acid decarboxylase from Rhizobium radiobacter WU-0108 under reverse reaction conditions. The enzyme carboxylated resorcinol, catechol, 5-methylresorcinol and three hydroxystilbenes (resveratrol, gnetol, and piceatannol) with high yields. Except for catechol, the structures of these substrates include a 1,3-dihydroxybenzene moiety. Other compounds gave no reaction products. The reaction products from resveratrol and gnetol were 2,6-dihydroxy-4-[(E)-2-(4-hydroxyphenyl)ethenyl]benzoic acid and 2,6-dihydroxy-4-[(E)-2-(2,6-dihydroxyphenyl)ethenyl]benzoic acid, respectively, as determined by mass spectrometry and nuclear magnetic resonance analyses. Kinetic analyses of the carboxylation reactions indicated that resveratrol and gnetol are better substrates than resorcinol or catechol.

    Original languageEnglish
    Pages (from-to)348-352
    Number of pages5
    JournalJournal of Molecular Catalysis B: Enzymatic
    Volume122
    DOIs
    Publication statusPublished - 2015 Dec 1

    Fingerprint

    Resveratrol
    Carboxylation
    Agrobacterium tumefaciens
    Carboxy-Lyases
    Benzoic acid
    Reaction products
    Acids
    Benzoic Acid
    Substrates
    Mass spectrometry
    Enzymes
    Nuclear magnetic resonance
    Mass Spectrometry
    Kinetics
    Magnetic Resonance Spectroscopy
    catechol
    2,3',5',6-tetrahydroxy-trans-stilbene
    resveratrol

    Keywords

    • Enzymatic carboxylation
    • Gnetol
    • Hydroxystilbene
    • Resveratrol
    • γ-Resorcylic acid decarboxylase

    ASJC Scopus subject areas

    • Biochemistry
    • Bioengineering
    • Catalysis
    • Process Chemistry and Technology

    Cite this

    Enzymatic carboxylation of hydroxystilbenes by the γ-resorcylic acid decarboxylase from Rhizobium radiobacter WU-0108 under reverse reaction conditions. / Sato, Masaru; Sakurai, Nozomu; Suzuki, Hideyuki; Shibata, Daisuke; Kino, Kuniki.

    In: Journal of Molecular Catalysis B: Enzymatic, Vol. 122, 01.12.2015, p. 348-352.

    Research output: Contribution to journalArticle

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    abstract = "We examined 66 aromatics for carboxylation by the γ-resorcylic acid decarboxylase from Rhizobium radiobacter WU-0108 under reverse reaction conditions. The enzyme carboxylated resorcinol, catechol, 5-methylresorcinol and three hydroxystilbenes (resveratrol, gnetol, and piceatannol) with high yields. Except for catechol, the structures of these substrates include a 1,3-dihydroxybenzene moiety. Other compounds gave no reaction products. The reaction products from resveratrol and gnetol were 2,6-dihydroxy-4-[(E)-2-(4-hydroxyphenyl)ethenyl]benzoic acid and 2,6-dihydroxy-4-[(E)-2-(2,6-dihydroxyphenyl)ethenyl]benzoic acid, respectively, as determined by mass spectrometry and nuclear magnetic resonance analyses. Kinetic analyses of the carboxylation reactions indicated that resveratrol and gnetol are better substrates than resorcinol or catechol.",
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    AU - Kino, Kuniki

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