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Rational Design of Biocatalytic Deuteration Platform of Aldehydes

Jian Xu, Yujiao Lou, Lanlan Wang, Zhiguo Wang, Weihua Xu, Wenqian Ma, Zhichun Chen, Xiaoyang Chen, Qi Wu

2021ACS Catalysis26 citationsDOI

Abstract

The rational design of a non-natural reactivity of an enzyme based on the understanding of catalytic mechanism remains a significant challenge. Herein, we report a biocatalytic synthesis of deuterated aldehydes via a ThDP-dependent enzyme-catalyzed hydrogen-isotope exchange (HIE) reaction. An MD-guided structure screening of ThDP-dependent enzymes was used to evaluate the feasibility of the HIE reaction. Under the guidance of the mechanism, protein engineering was then utilized to expand this method to a diverse range of substrates through the rational generation of several key mutants, which have suitable binding pockets in favor of the production of corresponding deuterated aldehydes in good yields and high D-incorporations, while blocking the undesired benzoin condensation reactions.

Topics & Concepts

Rational designChemistryCatalysisBiocatalysisDeuteriumCombinatorial chemistryReactivity (psychology)Kinetic isotope effectEnzymeOrganic chemistryComputational chemistryReaction mechanismStereochemistryNanotechnologyMaterials scienceMedicineQuantum mechanicsPathologyPhysicsAlternative medicineChemical Reactions and IsotopesChemical Synthesis and AnalysisAsymmetric Hydrogenation and Catalysis
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