Tailoring a Soluble Diiron Monooxygenase for Synthesis of Aromatic N-oxides
AbstractThe aromatic N-oxides have received increased attention over the last few years due to their potential application in medicine, agriculture and organic chemistry. As a green alternative in their synthesis, the biocatalytic method employing whole cells of Escherichia coli bearing phenol monooxygenase like protein PmlABCDEF (from here on – PML monooxygenase) has been introduced. In this work, site-directed mutagenesis was used to study the contributions of active site neighboring residues I106, A113, G109, F181, F200, F209 to the regiospecificity of N-oxidation. Based on chromogenic indole oxidation screening, a collection of PML mutants with altered catalytic properties was created. Among the tested mutants, the A113G variant acquired the most distinguishable N-oxidations capacity. This new variant of PML was able to produce dioxides (quinoxaline-1,4-dioxide, 2,5-dimethylpyrazine-1,4-dioxide) and specific mono-N-oxides (2,3,5-trimethylpyrazine-1-oxide) that were unachievable using the wild type PML. This mutant also featured reshaped regioselectivity as N-oxidation shifted towards quinazoline-1-oxide compared to quinazoline-3-oxide that is produced by the wild type PML. View Full-Text
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Petkevičius, V.; Vaitekūnas, J.; Vaitkus, D.; Čėnas, N.; Meškys, R. Tailoring a Soluble Diiron Monooxygenase for Synthesis of Aromatic N-oxides. Catalysts 2019, 9, 356.
Petkevičius V, Vaitekūnas J, Vaitkus D, Čėnas N, Meškys R. Tailoring a Soluble Diiron Monooxygenase for Synthesis of Aromatic N-oxides. Catalysts. 2019; 9(4):356.Chicago/Turabian Style
Petkevičius, Vytautas; Vaitekūnas, Justas; Vaitkus, Dovydas; Čėnas, Narimantas; Meškys, Rolandas. 2019. "Tailoring a Soluble Diiron Monooxygenase for Synthesis of Aromatic N-oxides." Catalysts 9, no. 4: 356.
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