Regio- and stereoselective oxygenation of proline derivatives by using microbial 2-oxoglutarate-dependent dioxygenases

Ryotaro Hara, Naoko Uchiumi, Naoko Okamoto, Kuniki Kino

    Research output: Contribution to journalArticle

    6 Citations (Scopus)

    Abstract

    We evaluated the substrate specificities of four proline cis-selective hydroxylases toward the efficient synthesis of proline derivatives. In an initial evaluation, 15 proline-related compounds were investigated as substrates. In addition to l-proline and l-pipecolinic acid, we found that 3,4-dehydro-l-proline, l-azetidine-2-carboxylic acid, cis-3-hydroxy-l-proline, and l-thioproline were also oxygenated. Subsequently, the product structures were determined, revealing cis-3,4-epoxy-l-proline, cis-3-hydroxy-l-azetidine-2-carboxylic acid, and 2,3-cis-3,4-cis-3,4-dihydroxy-l-proline.

    Original languageEnglish
    Pages (from-to)1384-1388
    Number of pages5
    JournalBioscience, Biotechnology, and Biochemistry
    Volume78
    Issue number8
    DOIs
    Publication statusPublished - 2014

    Fingerprint

    Dioxygenases
    Oxygenation
    Proline
    Derivatives
    Azetidinecarboxylic Acid
    Hydroxyproline
    Substrates
    Mixed Function Oxygenases
    alpha-ketoglutaric acid
    Substrate Specificity
    Acids

    Keywords

    • dihydroxyproline
    • dioxygenase
    • hydroxylase
    • oxygenation
    • proline derivative

    ASJC Scopus subject areas

    • Medicine(all)

    Cite this

    Regio- and stereoselective oxygenation of proline derivatives by using microbial 2-oxoglutarate-dependent dioxygenases. / Hara, Ryotaro; Uchiumi, Naoko; Okamoto, Naoko; Kino, Kuniki.

    In: Bioscience, Biotechnology, and Biochemistry, Vol. 78, No. 8, 2014, p. 1384-1388.

    Research output: Contribution to journalArticle

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    AB - We evaluated the substrate specificities of four proline cis-selective hydroxylases toward the efficient synthesis of proline derivatives. In an initial evaluation, 15 proline-related compounds were investigated as substrates. In addition to l-proline and l-pipecolinic acid, we found that 3,4-dehydro-l-proline, l-azetidine-2-carboxylic acid, cis-3-hydroxy-l-proline, and l-thioproline were also oxygenated. Subsequently, the product structures were determined, revealing cis-3,4-epoxy-l-proline, cis-3-hydroxy-l-azetidine-2-carboxylic acid, and 2,3-cis-3,4-cis-3,4-dihydroxy-l-proline.

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