Abstract
Deuterated unsaturated fragments have gained increasing attention because of their roles in understanding reaction mechanisms and pharmaceutical potentials. Due to the difficulties of the existing synthetic methods, it is highly desirable to develop an effective, highly site selective, and environmentally friendly method to introduce deuterium into unsaturated fragments. Herein, we describe a biocatalytic hydrogen isotope exchange (HIE) reaction of unsaturated fragments to form C(sp2)–D bonds catalyzed by an engineered ferulic acid decarboxylase from Aspergillus niger (AnFdc), which naturally catalyzes the reversible transformation of cinnamic acid to styrene and CO2. AnFdc displayed promising synthetic potentials and a broad compatibility of substrates, affording a series of deuterated aromatic heterocycles and styrene derivatives with high yields, site selectivity, and D incorporations.
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