Preparation of chiral alcohols by enantioselective reduction of prochiral ketones with Sinapis alba seeds as biocatalyst

•Yellow mustard seeds have enzymes that can be applied in reduction reactions of carbonyl compounds.•S-configuration products with excellent enantiomeric excess values were obtained in the reduction reactions with acetophenone.•The presence of PVP in the reaction medium reversed the (R) configuratio...

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Veröffentlicht in:Industrial crops and products 2019-12, Vol.141, p.111729, Article 111729
Hauptverfasser: de Sousa, Emerson Yvay Almeida, da Silva, Francisco Felipe Maia, de Souza, Juliana Maria Oliveira, Ferreira, Daniele Alves, de Lemos, Telma Leda Gomes, Monte, Francisco José Queiroz
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Sprache:eng
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Zusammenfassung:•Yellow mustard seeds have enzymes that can be applied in reduction reactions of carbonyl compounds.•S-configuration products with excellent enantiomeric excess values were obtained in the reduction reactions with acetophenone.•The presence of PVP in the reaction medium reversed the (R) configuration of the respective meta-substituted alcohol. The objective of this work is to apply yellow mustard seeds in the enzymatic reduction (biocatalysis) of acetophenone and its derivatives, providing a new biocatalyst for this type of reduction. The reaction parameters were optimized from acetophenone, resulting in 1-phenylethanol, with 68.5% conversion yield and 53% enantiomeric excess (e.e.), analyzed by GC and HPLC, respectively. Reactions to acetophenone and its derivatives were conducted in aqueous medium using buffers pH 6.0 and pH 6.5 in the presence of PVP. A polymer that can act as a protector preventing oxidation of peroxidase enzymes. The results for the derivatives presented low yields (4–18%: substances 5, 7 and 8), moderate (28–40%: substances 3, 4 and 6) and optimum (81%: substance 2) yields, with enantiomeric excesses varying from good to excellent results. Meta-substituted derivatives showed inversion of configuration in the presence of PVP. The biocatalyst was also tested in reactions with other carbonyl compounds, presenting moderate results. In this way, this work offers a new perspective of the application of PVP in biocatalysis reactions and a new biocatalyst for future applications.
ISSN:0926-6690
1872-633X
DOI:10.1016/j.indcrop.2019.111729