Biocatalytic reduction of activated cinnamic acid derivatives asymmetric reduction of C=C double bonds using Johnson Matthey enzymes

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Abstract

The asymmetric reduction of C=C double bonds is a sought-after chemical transformation to obtain chiral molecules used in the synthesis of fine chemicals. Biocatalytic C=C double bond reduction is a particularly interesting transformation complementary to more established chemocatalytic methods. The enzymes capable of catalysing this reaction are called ene-reductases (ENEs). For the reaction to take place, ENEs need an electron withdrawing group (EWG) in conjugation with the double bond. Especially favourable EWGs are carbonyls and nitro groups; other EWGs, such as carboxylic acids, esters or nitriles, often give poor results. In this work, a substrate engineering strategy is proposed whereby a simple transformation of the carboxylic acid into a fluorinated ester or a cyclic imide allows to increase the ability of ENEs to reduce the conjugated double bond. Up to complete conversion of the substrates tested was observed with enzymes ENE-105 and *ENE-69.

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APA

Staniland, S., Angelini, T., Pushpanath, A., Bornadel, A., Siirola, E., Bisagni, S., … Domínguez, B. (2020). Biocatalytic reduction of activated cinnamic acid derivatives asymmetric reduction of C=C double bonds using Johnson Matthey enzymes. Johnson Matthey Technology Review, 64(4), 529–536. https://doi.org/10.1595/205651320X15954136194837

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