Open AccessBiocatalytic Reduction of Activated Cinnamic Acid Derivatives : Asymmetric reduction of C=C double bonds using Johnson Matthey enzymes
Author(s) -
Samantha Staniland,
Tommaso Angelini,
Ahir Pushpanath,
Amin Bornadel,
Elina Siirola,
Serena Bisagni,
Antonio ZanottiGerosa,
Beatriz Domı́nguez
Publication year - 2020
Publication title -
johnson matthey technology review
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.571
H-Index - 49
ISSN - 2056-5135
DOI - 10.1595/205651320x16001815466116
Subject(s) - chemistry , double bond , conjugated system , imide , enzyme , substrate (aquarium) , functional group , carboxylic acid , stereochemistry , combinatorial chemistry , nitro , selective reduction , cinnamic acid , biocatalysis , ene reaction , organic chemistry , catalysis , reaction mechanism , polymer , oceanography , alkyl , geology
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.