Enantioselective preparation of δ-valerolactones with horse liver alcohol dehydrogenase

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. Not just horsing around: Horse liver alcohol dehydrogenase is found to be a versatile biocatalyst for the desymmetrization of 3-arylpentane-1,5-diols through a two-step one-pot oxidation. The catalytic performance of horse liver alcohol dehydrogenase (HLADH) is studied with several cofactor regeneration systems and cosolvents. Docking studies reveal the importance of pattern substitution in the selectivity and activity of this biotransformation. © 2014 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.