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A Biocatalytic Synthesis of Heteroaromatic N ‐Oxides by Whole Cells of Escherichia coli Expressing the Multicomponent, Soluble Di‐Iron Monooxygenase (SDIMO) PmlABCDEF
Author(s) -
Petkevičius Vytautas,
Vaitekūnas Justas,
Tauraitė Daiva,
Stankevičiūtė Jonita,
Šarlauskas Jonas,
Čėnas Narimantas,
Meškys Rolandas
Publication year - 2019
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.201801491
Subject(s) - chemistry , biocatalysis , oxidizing agent , catalysis , reagent , organic chemistry , escherichia coli , monooxygenase , environmentally friendly , combinatorial chemistry , enzyme , reaction mechanism , biochemistry , cytochrome p450 , gene , ecology , biology
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.