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Lipase-mediated Baeyer–Villiger oxidation of benzylcyclopentanones in ester solvents and deep eutectic solvents

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 effectiv...

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Autores principales: Mazur, Marcelina, Janeczko, Tomasz, Gładkowski, Witold
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Nature Publishing Group UK 2022
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9427991/
https://www.ncbi.nlm.nih.gov/pubmed/36042323
http://dx.doi.org/10.1038/s41598-022-18913-2
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author Mazur, Marcelina
Janeczko, Tomasz
Gładkowski, Witold
author_facet Mazur, Marcelina
Janeczko, Tomasz
Gładkowski, Witold
author_sort Mazur, Marcelina
collection PubMed
description 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.
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spelling pubmed-94279912022-09-01 Lipase-mediated Baeyer–Villiger oxidation of benzylcyclopentanones in ester solvents and deep eutectic solvents Mazur, Marcelina Janeczko, Tomasz Gładkowski, Witold Sci Rep Article 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. Nature Publishing Group UK 2022-08-30 /pmc/articles/PMC9427991/ /pubmed/36042323 http://dx.doi.org/10.1038/s41598-022-18913-2 Text en © The Author(s) 2022 https://creativecommons.org/licenses/by/4.0/Open Access This article is licensed under a Creative Commons Attribution 4.0 International License, which permits use, sharing, adaptation, distribution and reproduction in any medium or format, as long as you give appropriate credit to the original author(s) and the source, provide a link to the Creative Commons licence, and indicate if changes were made. The images or other third party material in this article are included in the article's Creative Commons licence, unless indicated otherwise in a credit line to the material. If material is not included in the article's Creative Commons licence and your intended use is not permitted by statutory regulation or exceeds the permitted use, you will need to obtain permission directly from the copyright holder. To view a copy of this licence, visit http://creativecommons.org/licenses/by/4.0/ (https://creativecommons.org/licenses/by/4.0/) .
spellingShingle Article
Mazur, Marcelina
Janeczko, Tomasz
Gładkowski, Witold
Lipase-mediated Baeyer–Villiger oxidation of benzylcyclopentanones in ester solvents and deep eutectic solvents
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
topic Article
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9427991/
https://www.ncbi.nlm.nih.gov/pubmed/36042323
http://dx.doi.org/10.1038/s41598-022-18913-2
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