Applying biocatalysis to the synthesis of diastereomerically enriched cyanohydrin mannosides

Ari Hietanen, Filip S. Ekholm, Reko Leino, Liisa T. Kanerva

    Tutkimustuotos: LehtiartikkeliArtikkeliTieteellinenvertaisarvioitu

    11 Sitaatiot (Scopus)

    Abstrakti

    Fully acetylated D- and L-alpha-mannosylacetaldehydes have been prepared and used as substrates to produce the corresponding cyanohydrins or cyanohydrin acetates with (2S) or (2R) configuration, respectively, at the cyanohydrin moiety. The (R)-oxynitrilase-catalysed synthesis and lipase-catalysed diastereomeric kinetic and dynamic kinetic resolutions were investigated. Sequential catalysis with almond meal [ an economic source of (R)-oxynitrilase] and Burkholderia cepacia lipase was shown to be a straightforward method that yielded the four diastereomeric target cyanohydrins, the absolute configurations of which were confirmed by (1)H NMR analysis.
    AlkuperäiskieliEi tiedossa
    Sivut6974–6980
    Sivumäärä7
    JulkaisuEuropean Journal of Organic Chemistry
    Numero36
    DOI - pysyväislinkit
    TilaJulkaistu - 2010
    OKM-julkaisutyyppiA1 Julkaistu artikkeli, soviteltu

    Keywords

    • Diastereoselectivity
    • Enzyme catalysis
    • Kinetic resolution

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