Production of Enantiopure Chiral Epoxides with <i>E. coli</i> Expressing Styrene Monooxygenase
Styrene monooxygenases are a group of highly selective enzymes able to catalyse the epoxidation of alkenes to corresponding chiral epoxides in excellent enantiopurity. Chiral compounds containing oxirane ring or products of their hydrolysis represent key building blocks and precursors in organic syn...
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MDPI AG
2021-03-01
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| Series: | Molecules |
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| Online Access: | https://www.mdpi.com/1420-3049/26/6/1514 |
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| author | Dominika Gyuranová Radka Štadániová Zuzana Hegyi Róbert Fischer Martin Rebroš |
| author_facet | Dominika Gyuranová Radka Štadániová Zuzana Hegyi Róbert Fischer Martin Rebroš |
| author_sort | Dominika Gyuranová |
| collection | DOAJ |
| description | Styrene monooxygenases are a group of highly selective enzymes able to catalyse the epoxidation of alkenes to corresponding chiral epoxides in excellent enantiopurity. Chiral compounds containing oxirane ring or products of their hydrolysis represent key building blocks and precursors in organic synthesis in the pharmaceutical industry, and many of them are produced on an industrial scale. Two-component recombinant styrene monooxygenase (SMO) from <i>Marinobacterium litorale</i> was expressed as a fused protein (StyAL2StyB) in <i>Escherichia coli</i> BL21(DE3). By high cell density fermentation, 35 g<sub>DCW</sub>/L of biomass with overexpressed SMO was produced. SMO exhibited excellent stability, broad substrate specificity, and enantioselectivity, as it remained active for months and converted a group of alkenes to corresponding chiral epoxides in high enantiomeric excess (˃95–99% ee). Optically pure (<i>S</i>)-4-chlorostyrene oxide, (<i>S</i>)-allylbenzene oxide, (2<i>R</i>,5<i>R</i>)-1,2:5,6-diepoxyhexane, 2-(3-bromopropyl)oxirane, and (<i>S</i>)-4-(oxiran-2-yl)butan-1-ol were prepared by whole-cell SMO. |
| first_indexed | 2024-03-10T13:21:52Z |
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| institution | Directory Open Access Journal |
| issn | 1420-3049 |
| language | English |
| last_indexed | 2024-03-10T13:21:52Z |
| publishDate | 2021-03-01 |
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| record_format | Article |
| series | Molecules |
| spelling | doaj.art-026f0e33f6f540e299e3b34e2e4737432023-11-21T09:55:04ZengMDPI AGMolecules1420-30492021-03-01266151410.3390/molecules26061514Production of Enantiopure Chiral Epoxides with <i>E. coli</i> Expressing Styrene MonooxygenaseDominika Gyuranová0Radka Štadániová1Zuzana Hegyi2Róbert Fischer3Martin Rebroš4Faculty of Chemical and Food Technology, Institute of Biotechnology, Slovak University of Technology in Bratislava, Radlinského 9, 812 37 Bratislava, SlovakiaFaculty of Chemical and Food Technology, Institute of Organic Chemistry, Catalysis and Petrochemistry, Slovak University of Technology in Bratislava, Radlinského 9, 812 37 Bratislava, SlovakiaFaculty of Chemical and Food Technology, Institute of Biotechnology, Slovak University of Technology in Bratislava, Radlinského 9, 812 37 Bratislava, SlovakiaFaculty of Chemical and Food Technology, Institute of Organic Chemistry, Catalysis and Petrochemistry, Slovak University of Technology in Bratislava, Radlinského 9, 812 37 Bratislava, SlovakiaFaculty of Chemical and Food Technology, Institute of Biotechnology, Slovak University of Technology in Bratislava, Radlinského 9, 812 37 Bratislava, SlovakiaStyrene monooxygenases are a group of highly selective enzymes able to catalyse the epoxidation of alkenes to corresponding chiral epoxides in excellent enantiopurity. Chiral compounds containing oxirane ring or products of their hydrolysis represent key building blocks and precursors in organic synthesis in the pharmaceutical industry, and many of them are produced on an industrial scale. Two-component recombinant styrene monooxygenase (SMO) from <i>Marinobacterium litorale</i> was expressed as a fused protein (StyAL2StyB) in <i>Escherichia coli</i> BL21(DE3). By high cell density fermentation, 35 g<sub>DCW</sub>/L of biomass with overexpressed SMO was produced. SMO exhibited excellent stability, broad substrate specificity, and enantioselectivity, as it remained active for months and converted a group of alkenes to corresponding chiral epoxides in high enantiomeric excess (˃95–99% ee). Optically pure (<i>S</i>)-4-chlorostyrene oxide, (<i>S</i>)-allylbenzene oxide, (2<i>R</i>,5<i>R</i>)-1,2:5,6-diepoxyhexane, 2-(3-bromopropyl)oxirane, and (<i>S</i>)-4-(oxiran-2-yl)butan-1-ol were prepared by whole-cell SMO.https://www.mdpi.com/1420-3049/26/6/1514styrene monooxygenasewhole-cell biocatalysischiral epoxides |
| spellingShingle | Dominika Gyuranová Radka Štadániová Zuzana Hegyi Róbert Fischer Martin Rebroš Production of Enantiopure Chiral Epoxides with <i>E. coli</i> Expressing Styrene Monooxygenase Molecules styrene monooxygenase whole-cell biocatalysis chiral epoxides |
| title | Production of Enantiopure Chiral Epoxides with <i>E. coli</i> Expressing Styrene Monooxygenase |
| title_full | Production of Enantiopure Chiral Epoxides with <i>E. coli</i> Expressing Styrene Monooxygenase |
| title_fullStr | Production of Enantiopure Chiral Epoxides with <i>E. coli</i> Expressing Styrene Monooxygenase |
| title_full_unstemmed | Production of Enantiopure Chiral Epoxides with <i>E. coli</i> Expressing Styrene Monooxygenase |
| title_short | Production of Enantiopure Chiral Epoxides with <i>E. coli</i> Expressing Styrene Monooxygenase |
| title_sort | production of enantiopure chiral epoxides with i e coli i expressing styrene monooxygenase |
| topic | styrene monooxygenase whole-cell biocatalysis chiral epoxides |
| url | https://www.mdpi.com/1420-3049/26/6/1514 |
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