Bioelectrochemical Synthesis of N-Heterocycles

Bioelectrochemical Synthesis of N-Heterocycles

Author: Angewandte Chemie International Edition

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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