Dobrijevic, D;
Benhamou, L;
Aliev, AE;
Méndez-Sánchez, D;
Dawson, N;
Baud, D;
Tappertzhofen, N;
... Ward, JM; + view all
(2019)
Metagenomic ene-reductases for the bioreduction of sterically challenging enones.
RSC Advances
, 9
(63)
pp. 36608-36614.
10.1039/c9ra06088j.
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Abstract
Ene-reductases (ERs) of the Old Yellow Enzyme family catalyse asymmetric reduction of activated alkenes providing chiral products. They have become an important method in the synthetic chemists' toolbox offering a sustainable alternative to metal-catalysed asymmetric reduction. Development of new biocatalytic alkene reduction routes, however needs easy access to novel biocatalysts. A sequence-based functional metagenomic approach was used to identify novel ERs from a drain metagenome. From the ten putative ER enzymes initially identified, eight exhibited activities towards widely accepted mono-cyclic substrates with several of the ERs giving high reaction yields and stereoselectivities. Two highly performing enzymes that displayed excellent co-solvent tolerance were used for the stereoselective reduction of sterically challenging bicyclic enones where the reactions proceeded in high yields, which is unprecedented to date with wild-type ERs. On a preparative enzymatic scale, reductions of Hajos–Parish, Wieland–Miescher derivatives and a tricyclic ketone proceeded with good to excellent yields.
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