Tailored photoenzymatic systems for selective reduction of aliphatic and aromatic nitro compounds fueled by light

Alejandro Prats Luján, Mohammad Faizan Bhat, Sona Tsaturyan, Ronald Merkerk, Haigen Fu and Gerrit J. Poelarends ()
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Alejandro Prats Luján: University of Groningen
Mohammad Faizan Bhat: University of Groningen
Sona Tsaturyan: University of Groningen
Ronald Merkerk: University of Groningen
Haigen Fu: Cornell University
Gerrit J. Poelarends: University of Groningen

Nature Communications, 2023, vol. 14, issue 1, 1-10

Abstract: Abstract The selective enzymatic reduction of nitroaliphatic and nitroaromatic compounds to aliphatic amines and amino-, azoxy- and azo-aromatics, respectively, remains a persisting challenge for biocatalysis. Here we demonstrate the light-powered, selective photoenzymatic synthesis of aliphatic amines and amino-, azoxy- and azo-aromatics from the corresponding nitro compounds. The nitroreductase from Bacillus amyloliquefaciens, in synergy with a photocatalytic system based on chlorophyll, promotes selective conversions of electronically-diverse nitroarenes into a series of aromatic amino, azoxy and azo products with excellent yield (up to 97%). The exploitation of an alternative nitroreductase from Enterobacter cloacae enables the tailoring of a photoenzymatic system for the challenging synthesis of aliphatic amines from nitroalkenes and nitroalkanes (up to 90% yield). This photoenzymatic reduction overcomes the competing bio-Nef reaction, typically hindering the complete enzymatic reduction of nitroaliphatics. The results highlight the usefulness of nitroreductases to create selective photoenzymatic systems for the synthesis of precious chemicals, and the effectiveness of chlorophyll as an innocuous photocatalyst, enabling the use of sunlight to drive the photobiocatalytic reactions.

Date: 2023
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DOI: 10.1038/s41467-023-41194-w

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