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Enantioselective Biocascade Catalysis with a Single Multifunctional Enzyme

Von Wiley-VCH zur Verfügung gestellt

A single multifunctional enzyme is reported that can promote biocatalytic cascades based on multiple stereoselective steps. Specifically, a 4-oxalocrotonate tautomerase (4-OT) enzyme can form enamine and iminium ion intermediates from aldehydes and enals to promote both a two-component reaction and a triple cascade characterized by different mechanisms and activation sequences.


Abstract

Asymmetric catalytic cascade processes offer direct access to complex chiral molecules from simple substrates and in a single step. In biocatalysis, cascades are generally designed by combining multiple enzymes, each catalyzing individual steps of a sequence. Herein, we report a different strategy for biocascades based on a single multifunctional enzyme that can promote multiple stereoselective steps of a domino process by mastering distinct catalytic mechanisms of substrate activation in a sequential way. Specifically, we have used an engineered 4-oxalocrotonate tautomerase (4-OT) enzyme with the ability to form both enamines and iminium ions and combine their mechanisms of catalysis in a complex sequence. This approach allowed us to activate aldehydes and enals toward the synthesis of enantiopure cyclohexene carbaldehydes. The multifunctional 4-OT enzymes could promote both a two-component reaction and a triple cascade characterized by different mechanisms and activation sequences.

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