Lipase-mediated Baeyer–Villiger oxidation of benzylcyclopentanones in ester solvents and deep eutectic solvents
Abstract This work presents the chemo-enzymatic Baeyer–Villiger oxidation of α-benzylcyclopentanones in ester solvents as well as deep eutectic solvents (DES). In the first part of the work the effect of selected reaction conditions on the reaction rate was determined. The oxidation process was most...
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| Format: | Article |
| Language: | English |
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Nature Portfolio
2022-08-01
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| Series: | Scientific Reports |
| Online Access: | https://doi.org/10.1038/s41598-022-18913-2 |
| _version_ | 1798032528891707392 |
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| author | Marcelina Mazur Tomasz Janeczko Witold Gładkowski |
| author_facet | Marcelina Mazur Tomasz Janeczko Witold Gładkowski |
| author_sort | Marcelina Mazur |
| collection | DOAJ |
| description | Abstract This work presents the chemo-enzymatic Baeyer–Villiger oxidation of α-benzylcyclopentanones in ester solvents as well as deep eutectic solvents (DES). In the first part of the work the effect of selected reaction conditions on the reaction rate was determined. The oxidation process was most effective in ethyl acetate at 55 °C, with the use of lipase B from Candida antarctica immobilized on acrylic resin and UHP as oxidant. Ultimately, these preliminary studies prompted the development of an effective method for the implementation of lipase-mediated Baeyer–Villiger oxidation of benzylcyclopentanones in DES. The highest conversion was indicated when the oxidizing agent was a component of DESs (minimal DESs). The fastest conversion of ketones to lactones was observed in a mixture of choline chloride with urea hydrogen peroxide. In this case, after 3 days, the conversion of the ketones to lactones products exceeded 92% for all substrates. As a result, two new lactones were obtained and fully characterized by spectroscopic data. |
| first_indexed | 2024-04-11T20:15:30Z |
| format | Article |
| id | doaj.art-088506e9291a421b891991649b33fd3f |
| institution | Directory Open Access Journal |
| issn | 2045-2322 |
| language | English |
| last_indexed | 2024-04-11T20:15:30Z |
| publishDate | 2022-08-01 |
| publisher | Nature Portfolio |
| record_format | Article |
| series | Scientific Reports |
| spelling | doaj.art-088506e9291a421b891991649b33fd3f2022-12-22T04:04:59ZengNature PortfolioScientific Reports2045-23222022-08-011211710.1038/s41598-022-18913-2Lipase-mediated Baeyer–Villiger oxidation of benzylcyclopentanones in ester solvents and deep eutectic solventsMarcelina Mazur0Tomasz Janeczko1Witold Gładkowski2Department of Food Chemistry and Biocatalysis, Wrocław University of Environmental and Life SciencesDepartment of Food Chemistry and Biocatalysis, Wrocław University of Environmental and Life SciencesDepartment of Food Chemistry and Biocatalysis, Wrocław University of Environmental and Life SciencesAbstract This work presents the chemo-enzymatic Baeyer–Villiger oxidation of α-benzylcyclopentanones in ester solvents as well as deep eutectic solvents (DES). In the first part of the work the effect of selected reaction conditions on the reaction rate was determined. The oxidation process was most effective in ethyl acetate at 55 °C, with the use of lipase B from Candida antarctica immobilized on acrylic resin and UHP as oxidant. Ultimately, these preliminary studies prompted the development of an effective method for the implementation of lipase-mediated Baeyer–Villiger oxidation of benzylcyclopentanones in DES. The highest conversion was indicated when the oxidizing agent was a component of DESs (minimal DESs). The fastest conversion of ketones to lactones was observed in a mixture of choline chloride with urea hydrogen peroxide. In this case, after 3 days, the conversion of the ketones to lactones products exceeded 92% for all substrates. As a result, two new lactones were obtained and fully characterized by spectroscopic data.https://doi.org/10.1038/s41598-022-18913-2 |
| spellingShingle | Marcelina Mazur Tomasz Janeczko Witold Gładkowski Lipase-mediated Baeyer–Villiger oxidation of benzylcyclopentanones in ester solvents and deep eutectic solvents Scientific Reports |
| title | Lipase-mediated Baeyer–Villiger oxidation of benzylcyclopentanones in ester solvents and deep eutectic solvents |
| title_full | Lipase-mediated Baeyer–Villiger oxidation of benzylcyclopentanones in ester solvents and deep eutectic solvents |
| title_fullStr | Lipase-mediated Baeyer–Villiger oxidation of benzylcyclopentanones in ester solvents and deep eutectic solvents |
| title_full_unstemmed | Lipase-mediated Baeyer–Villiger oxidation of benzylcyclopentanones in ester solvents and deep eutectic solvents |
| title_short | Lipase-mediated Baeyer–Villiger oxidation of benzylcyclopentanones in ester solvents and deep eutectic solvents |
| title_sort | lipase mediated baeyer villiger oxidation of benzylcyclopentanones in ester solvents and deep eutectic solvents |
| url | https://doi.org/10.1038/s41598-022-18913-2 |
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