Enzymatic Kolbe-Schmitt reaction to form salicylic acid from phenol: Enzymatic characterization and gene identification of a novel enzyme, Trichosporon moniliiforme salicylic acid decarboxylase

Kotaro Kirimura, Hiroaki Gunji, Rumiko Wakayama, Takasumi Hattori, Yoshitaka Ishii

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    42 Citations (Scopus)

    Abstract

    Salicylic acid decarboxylase (Sdc) can produce salicylic acid from phenol; it was found in the yeast Trichosporon moniliiforme WU-0401 and was for the first time enzymatically characterized, with the sdc gene heterologously expressed. Sdc catalyzed both reactions: decarboxylation of salicylic acid to phenol and the carboxylation of phenol to form salicylic acid without any byproducts. Both reactions were detected without the addition of any cofactors and occurred even in the presence of oxygen, suggesting that this Sdc is reversible, nonoxidative, and oxygen insensitive. Therefore, it is readily applicable in the selective production of salicylic acid from phenol, the enzymatic Kolbe-Schmitt reaction. The deduced amino acid sequence of the gene, sdc, encoding Sdc comprises 350 amino acid residues corresponding to a 40-kDa protein. The recombinant Escherichia coli BL21(DE3) expressing sdc converted phenol to salicylic acid with a 27% (mol/mol) yield at 30 °C for 9 h.

    Original languageEnglish
    Pages (from-to)279-284
    Number of pages6
    JournalBiochemical and Biophysical Research Communications
    Volume394
    Issue number2
    DOIs
    Publication statusPublished - 2010 Apr 2

    Fingerprint

    Trichosporon
    Carboxy-Lyases
    Salicylic Acid
    Phenol
    Genes
    Enzymes
    Carboxylation
    Oxygen
    Amino Acids
    Decarboxylation
    Gene encoding
    Yeast
    Escherichia coli
    Byproducts
    Amino Acid Sequence
    Yeasts

    Keywords

    • Enzymatic Kolbe-Schmitt reaction
    • Reversible decarboxylase
    • Salicylic acid decarboxylase
    • Selective production
    • Trichosporon moniliiforme

    ASJC Scopus subject areas

    • Biochemistry
    • Biophysics
    • Cell Biology
    • Molecular Biology

    Cite this

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    title = "Enzymatic Kolbe-Schmitt reaction to form salicylic acid from phenol: Enzymatic characterization and gene identification of a novel enzyme, Trichosporon moniliiforme salicylic acid decarboxylase",
    abstract = "Salicylic acid decarboxylase (Sdc) can produce salicylic acid from phenol; it was found in the yeast Trichosporon moniliiforme WU-0401 and was for the first time enzymatically characterized, with the sdc gene heterologously expressed. Sdc catalyzed both reactions: decarboxylation of salicylic acid to phenol and the carboxylation of phenol to form salicylic acid without any byproducts. Both reactions were detected without the addition of any cofactors and occurred even in the presence of oxygen, suggesting that this Sdc is reversible, nonoxidative, and oxygen insensitive. Therefore, it is readily applicable in the selective production of salicylic acid from phenol, the enzymatic Kolbe-Schmitt reaction. The deduced amino acid sequence of the gene, sdc, encoding Sdc comprises 350 amino acid residues corresponding to a 40-kDa protein. The recombinant Escherichia coli BL21(DE3) expressing sdc converted phenol to salicylic acid with a 27{\%} (mol/mol) yield at 30 °C for 9 h.",
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    AU - Gunji, Hiroaki

    AU - Wakayama, Rumiko

    AU - Hattori, Takasumi

    AU - Ishii, Yoshitaka

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