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Enantioselective Preparation of δ-Valerolactones with Horse Liver Alcohol Dehydrogenase

Authors

  • Alba Díaz-Rodríguez,

    1. Department of Organic and Inorganic Chemistry, University of Oviedo, C/Julián Clavería, 33006 Oviedo (Spain), Fax: (+34) 985103448
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  • Javier Iglesias-Fernández,

    1. Institut de Química Teòrica i Computacional (IQTCUB), Universitat de Barcelona, Martí i Franquès 1, 08028 Barcelona (Spain)
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  • Carme Rovira,

    1. Institut de Química Teòrica i Computacional (IQTCUB), Universitat de Barcelona, Martí i Franquès 1, 08028 Barcelona (Spain)
    2. Institució Catalana de Recerca i Estudis Avançats (ICREA), Passeig Lluis Companys 23, 08020 Barcelona (Spain)
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  • Vicente Gotor-Fernández

    Corresponding author
    1. Department of Organic and Inorganic Chemistry, University of Oviedo, C/Julián Clavería, 33006 Oviedo (Spain), Fax: (+34) 985103448
    • Department of Organic and Inorganic Chemistry, University of Oviedo, C/Julián Clavería, 33006 Oviedo (Spain), Fax: (+34) 985103448

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Abstract

Horse liver alcohol dehydrogenase (HLADH) has been found to be a versatile biocatalyst for the desymmetrization of prochiral 3-arylpentane-1,5-diols, based on a two-step one-pot oxidation. This procedure has allowed the formation of valuable (S)-lactones in good to excellent conversions and enantiomeric excess. The catalytic performance of HLADH has been studied using several cofactor regeneration systems and cosolvents, finding great improvements in terms of activity with L-lactate dehydrogenase, while the stereoselectivity of the process was significantly improved when using tetrahydrofuran. Docking studies has revealed the pattern substitution importance in the selectivity and activity of this oxidative process.

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