A coenzyme-independent decarboxylase/oxygenase cascade for the efficient synthesis of vanillin

Toshiki Furuya, Misa Miura, Kuniki Kino

    Research output: Contribution to journalArticle

    15 Citations (Scopus)

    Abstract

    Vanillin is one of the most widely used flavor compounds in the world as well as a promising versatile building block. The biotechnological production of vanillin from plant-derived ferulic acid has attracted much attention as a new alternative to chemical synthesis. One limitation of the known metabolic pathway to vanillin is its requirement for expensive coenzymes. Here, we developed a novel route to vanillin from ferulic acid that does not require any coenzymes. This artificial pathway consists of a coenzyme-independent decarboxylase and a coenzyme-independent oxygenase. When Escherichia coli cells harboring the decarboxylase/oxygenase cascade were incubated with ferulic acid, the cells efficiently synthesized vanillin (8.0 mM, 1.2 g L(-1) ) via 4-vinylguaiacol in one pot, without the generation of any detectable aromatic by-products. The efficient method described here might be applicable to the synthesis of other high-value chemicals from plant-derived aromatics.

    Original languageEnglish
    Pages (from-to)2248-2254
    Number of pages7
    JournalChembiochem : a European journal of chemical biology
    Volume15
    Issue number15
    DOIs
    Publication statusPublished - 2014 Oct 13

    Fingerprint

    ferulic acid
    Oxygenases
    Carboxy-Lyases
    Coenzymes
    Flavor compounds
    Phytochemicals
    Metabolic Networks and Pathways
    Escherichia coli
    Byproducts
    vanillin

    Keywords

    • biocatalysis
    • cascade reaction
    • decarboxylation
    • oxidation
    • sustainable chemistry

    ASJC Scopus subject areas

    • Biochemistry
    • Molecular Medicine
    • Molecular Biology
    • Organic Chemistry

    Cite this

    A coenzyme-independent decarboxylase/oxygenase cascade for the efficient synthesis of vanillin. / Furuya, Toshiki; Miura, Misa; Kino, Kuniki.

    In: Chembiochem : a European journal of chemical biology, Vol. 15, No. 15, 13.10.2014, p. 2248-2254.

    Research output: Contribution to journalArticle

    @article{c945a177c6754264af22e874fbdf0b3b,
    title = "A coenzyme-independent decarboxylase/oxygenase cascade for the efficient synthesis of vanillin",
    abstract = "Vanillin is one of the most widely used flavor compounds in the world as well as a promising versatile building block. The biotechnological production of vanillin from plant-derived ferulic acid has attracted much attention as a new alternative to chemical synthesis. One limitation of the known metabolic pathway to vanillin is its requirement for expensive coenzymes. Here, we developed a novel route to vanillin from ferulic acid that does not require any coenzymes. This artificial pathway consists of a coenzyme-independent decarboxylase and a coenzyme-independent oxygenase. When Escherichia coli cells harboring the decarboxylase/oxygenase cascade were incubated with ferulic acid, the cells efficiently synthesized vanillin (8.0 mM, 1.2 g L(-1) ) via 4-vinylguaiacol in one pot, without the generation of any detectable aromatic by-products. The efficient method described here might be applicable to the synthesis of other high-value chemicals from plant-derived aromatics.",
    keywords = "biocatalysis, cascade reaction, decarboxylation, oxidation, sustainable chemistry",
    author = "Toshiki Furuya and Misa Miura and Kuniki Kino",
    year = "2014",
    month = "10",
    day = "13",
    doi = "10.1002/cbic.201402215",
    language = "English",
    volume = "15",
    pages = "2248--2254",
    journal = "ChemBioChem",
    issn = "1439-4227",
    publisher = "Wiley-VCH Verlag",
    number = "15",

    }

    TY - JOUR

    T1 - A coenzyme-independent decarboxylase/oxygenase cascade for the efficient synthesis of vanillin

    AU - Furuya, Toshiki

    AU - Miura, Misa

    AU - Kino, Kuniki

    PY - 2014/10/13

    Y1 - 2014/10/13

    N2 - Vanillin is one of the most widely used flavor compounds in the world as well as a promising versatile building block. The biotechnological production of vanillin from plant-derived ferulic acid has attracted much attention as a new alternative to chemical synthesis. One limitation of the known metabolic pathway to vanillin is its requirement for expensive coenzymes. Here, we developed a novel route to vanillin from ferulic acid that does not require any coenzymes. This artificial pathway consists of a coenzyme-independent decarboxylase and a coenzyme-independent oxygenase. When Escherichia coli cells harboring the decarboxylase/oxygenase cascade were incubated with ferulic acid, the cells efficiently synthesized vanillin (8.0 mM, 1.2 g L(-1) ) via 4-vinylguaiacol in one pot, without the generation of any detectable aromatic by-products. The efficient method described here might be applicable to the synthesis of other high-value chemicals from plant-derived aromatics.

    AB - Vanillin is one of the most widely used flavor compounds in the world as well as a promising versatile building block. The biotechnological production of vanillin from plant-derived ferulic acid has attracted much attention as a new alternative to chemical synthesis. One limitation of the known metabolic pathway to vanillin is its requirement for expensive coenzymes. Here, we developed a novel route to vanillin from ferulic acid that does not require any coenzymes. This artificial pathway consists of a coenzyme-independent decarboxylase and a coenzyme-independent oxygenase. When Escherichia coli cells harboring the decarboxylase/oxygenase cascade were incubated with ferulic acid, the cells efficiently synthesized vanillin (8.0 mM, 1.2 g L(-1) ) via 4-vinylguaiacol in one pot, without the generation of any detectable aromatic by-products. The efficient method described here might be applicable to the synthesis of other high-value chemicals from plant-derived aromatics.

    KW - biocatalysis

    KW - cascade reaction

    KW - decarboxylation

    KW - oxidation

    KW - sustainable chemistry

    UR - http://www.scopus.com/inward/record.url?scp=85027943031&partnerID=8YFLogxK

    UR - http://www.scopus.com/inward/citedby.url?scp=85027943031&partnerID=8YFLogxK

    U2 - 10.1002/cbic.201402215

    DO - 10.1002/cbic.201402215

    M3 - Article

    C2 - 25164030

    AN - SCOPUS:85027943031

    VL - 15

    SP - 2248

    EP - 2254

    JO - ChemBioChem

    JF - ChemBioChem

    SN - 1439-4227

    IS - 15

    ER -