Bioelectrochemical Synthesis of N-Heterocycles

  • Author: Angewandte Chemie International Edition
  • Published Date: 28 May 2020
  • Source / Publisher: Angewandte Chemie International Edition/Wiley-VCH
  • Copyright: Wiley-VCH Verlag GmbH & Co. KGaA
thumbnail image: Bioelectrochemical Synthesis of N-Heterocycles

Reactions driven by electricity are clean, easy to tune, and can be sustainable when coupled with renewable energy sources. Enzymatic reactions can be combined with this approach in a bioelectrochemical cell. Such cells are powered by electricity, and they can be used to selectively synthesize fine chemicals.

Lars Lauterbach, Technical University of Berlin, Germany, and colleagues have developed a scalable system that uses the gaseous products of electrolysis to power a synthetic enzymatic cascade in a continuous flow reactor. The enzymatic cascade is used to convert diamines into methylated N-heterocycles. H2 and O2 are generated by electrochemical water splitting using an iron–nickel sulfide (pentlandite) and a nickel catalyst for the H2- and O2-evolving reactions, respectively. The gases are then transferred into a flow system via a permeable membrane.

The electrolytic cell (pictured in yellow) is coupled to a packed column (pictured in green) containing a hydrogenase and catalase, immobilized on Amberlite, and an amine oxidase and imine reductase (IRED), immobilized on an the enzyme carrier EziGTM. The enzyme cascade functions with the help of a cofactor, nicotinamide adenine dinucleotide (NAD).



Using this setup, the team synthesized a range of methylated piperidines from diamines and, by including D2O in the biotransformation, they performed regioselective isotopic labeling (pictured below).




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