A Biocatalytic Synthesis of Heteroaromatic N‐Oxides by Whole Cells of Escherichia coli Expressing the Multicomponent, Soluble Di‐Iron Monooxygenase (SDIMO) PmlABCDEF

Aromatic N‐oxides (ArN−OX) are desirable biologically active compounds with a potential for application in pharmacy and agriculture industries. As biocatalysis is making a great impact in organic synthesis, there is still a lack of efficient and convenient enzyme‐based techniques for the production...

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Bibliographic Details
Published in:Advanced synthesis & catalysis 2019-06, Vol.361 (11), p.2456-2465
Main Authors: Petkevičius, Vytautas, Vaitekūnas, Justas, Tauraitė, Daiva, Stankevičiūtė, Jonita, Šarlauskas, Jonas, Čėnas, Narimantas, Meškys, Rolandas
Format: Article
Language:English
Subjects:
Aromatic compounds
Bacteria
Biocatalysis
chemoselectivity
E coli
Iron
nitrogen heterocycles
Oxidation
Oxides
Oxidizing agents
Pyrazines
Pyridines
Pyrimidines
Reagents
regioselectivity
soluble di-iron monooxygenase
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Summary:Aromatic N‐oxides (ArN−OX) are desirable biologically active compounds with a potential for application in pharmacy and agriculture industries. As biocatalysis is making a great impact in organic synthesis, there is still a lack of efficient and convenient enzyme‐based techniques for the production of aromatic N‐oxides. In this study, a recombinant soluble di‐iron monooxygenase (SDIMO) PmlABCDEF overexpressed in Escherichia coli was showed to produce various aromatic N‐oxides. Out of 98 tested N‐heterocycles, seventy were converted to the corresponding N‐oxides without any side oxidation products. This whole‐cell biocatalyst showed a high activity towards pyridines, pyrazines, and pyrimidines. It was also capable of oxidizing bulky N‐heterocycles with two or even three aromatic rings. Being entirely biocatalytic, our approach provides an environmentally friendly and mild method for the production of aromatic N‐oxides avoiding the use of strong oxidants, organometallic catalysts, undesirable solvents, or other environment unfriendly reagents.
ISSN:1615-4150
1615-4169
DOI:10.1002/adsc.201801491