Applying biocatalysis to the synthesis of diastereomerically enriched cyanohydrin mannosides

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

    Forskningsoutput: TidskriftsbidragArtikelVetenskapligPeer review

    11 Citeringar (Scopus)

    Sammanfattning

    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.
    OriginalspråkOdefinierat/okänt
    Sidor (från-till)6974–6980
    Antal sidor7
    TidskriftEuropean Journal of Organic Chemistry
    Utgåva36
    DOI
    StatusPublicerad - 2010
    MoE-publikationstypA1 Tidskriftsartikel-refererad

    Nyckelord

    • Diastereoselectivity
    • Enzyme catalysis
    • Kinetic resolution

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