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

Ryotaro Hara, Naoko Uchiumi, Naoko Okamoto, Kuniki Kino

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    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
    Issue number8
    Publication statusPublished - 2014



    • dihydroxyproline
    • dioxygenase
    • hydroxylase
    • oxygenation
    • proline derivative

    ASJC Scopus subject areas

    • Medicine(all)

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