Exploring the Substrate Scope and Catalytic Promiscuity of Nitroreductase‐Like Enzymes

Flavin‐dependent nitroreductases are gaining attention as biocatalysts for the synthesis of pharmaceutically active compounds and their precursors. Here, we examined a panel of nitroreductase‐like flavoenzymes for their reductase activity towards a wide variety of aromatic and aliphatic nitro compou...

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Bibliographic Details
Published in:Advanced synthesis & catalysis 2024-11, Vol.366 (22), p.4679-4687
Main Authors: Luján, Alejandro Prats, Bhat, Mohammad Faizan, Saravanan, Thangavelu, Poelarends, Gerrit J.
Format: Article
Language:English
Subjects:
Aromatic compounds
Carbonyl compounds
Carbonyls
Catalytic converters
Chemical synthesis
Chemoselectivity
Enantiomers
Ene-reductase
Enzymes
Flavoenzyme
Nitro compounds
Nitroreductase
Promiscuity
Reductases
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Summary:Flavin‐dependent nitroreductases are gaining attention as biocatalysts for the synthesis of pharmaceutically active compounds and their precursors. Here, we examined a panel of nitroreductase‐like flavoenzymes for their reductase activity towards a wide variety of aromatic and aliphatic nitro compounds, nitroolefins, and α,β‐unsaturated carbonyl compounds. Several of these flavoenzymes displayed high reductase activity and achieved excellent conversion of diverse nitroarenes, nitroolefins and α,β‐unsaturated carbonyl compounds, accomplishing good product yields in semi‐preparative scale reactions (up to 97%). In addition to the catalytic promiscuity of several of these flavoenzymes, being able to perform the reduction of nitro groups (nitroreductase activity) as well as C=C groups (ene‐reductase activity), this study also revealed that some flavoenzymes exhibit high chemo‐, regio‐ and/or enantioselectivity, making them attractive enzymes for use in organic synthesis.
ISSN:1615-4150
1615-4169
DOI:10.1002/adsc.202400220