Lipase‐Catalysed Enzymatic Kinetic Resolution of Aromatic Morita‐Baylis‐Hillman Derivatives by Hydrolysis and Transesterification
Abstract Acylated Morita‐Baylis‐Hillman (MBH) adducts were synthesised and subjected to enzymatic kinetic resolution (EKR) by hydrolysis employing various lipase enzymes: from P. fluorescens, P. cepacia (PCL), C. antarctica A (CAL−A), C. antarctica B (CAL−B) and Novozyme 435. In a number of instance...
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crwiley:10.1002/cbic.202200435 2024-09-15T17:42:14+00:00 Lipase‐Catalysed Enzymatic Kinetic Resolution of Aromatic Morita‐Baylis‐Hillman Derivatives by Hydrolysis and Transesterification Mathebula, Nompumelelo P. Sheldon, Roger A. Bode, Moira L. University of the Witwatersrand, Johannesburg 2022 http://dx.doi.org/10.1002/cbic.202200435 https://onlinelibrary.wiley.com/doi/pdf/10.1002/cbic.202200435 https://onlinelibrary.wiley.com/doi/full-xml/10.1002/cbic.202200435 en eng Wiley http://creativecommons.org/licenses/by-nc/4.0/ ChemBioChem volume 23, issue 21 ISSN 1439-4227 1439-7633 journal-article 2022 crwiley https://doi.org/10.1002/cbic.202200435 2024-08-13T04:18:14Z Abstract Acylated Morita‐Baylis‐Hillman (MBH) adducts were synthesised and subjected to enzymatic kinetic resolution (EKR) by hydrolysis employing various lipase enzymes: from P. fluorescens, P. cepacia (PCL), C. antarctica A (CAL−A), C. antarctica B (CAL−B) and Novozyme 435. In a number of instances enantiopure Morita‐Baylis‐Hillman acetates or butyrates and their corresponding hydrolysed MBH adducts were obtained with ee values of >90 %, at ca. 50 % conversion, corresponding to enantiomeric ratio (E) values of >200. Enantioselective transesterification reactions on MBH adducts was achieved using acyl anhydrides in THF or the greener organic solvent 2‐MeTHF in the presence of CAL−A. This is the first report of successful lipase‐catalysed EKR of aromatic MBH adducts by transesterification in organic medium. Article in Journal/Newspaper Antarc* Antarctica Wiley Online Library ChemBioChem 23 21 |
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English |
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Abstract Acylated Morita‐Baylis‐Hillman (MBH) adducts were synthesised and subjected to enzymatic kinetic resolution (EKR) by hydrolysis employing various lipase enzymes: from P. fluorescens, P. cepacia (PCL), C. antarctica A (CAL−A), C. antarctica B (CAL−B) and Novozyme 435. In a number of instances enantiopure Morita‐Baylis‐Hillman acetates or butyrates and their corresponding hydrolysed MBH adducts were obtained with ee values of >90 %, at ca. 50 % conversion, corresponding to enantiomeric ratio (E) values of >200. Enantioselective transesterification reactions on MBH adducts was achieved using acyl anhydrides in THF or the greener organic solvent 2‐MeTHF in the presence of CAL−A. This is the first report of successful lipase‐catalysed EKR of aromatic MBH adducts by transesterification in organic medium. |
author2 |
University of the Witwatersrand, Johannesburg |
format |
Article in Journal/Newspaper |
author |
Mathebula, Nompumelelo P. Sheldon, Roger A. Bode, Moira L. |
spellingShingle |
Mathebula, Nompumelelo P. Sheldon, Roger A. Bode, Moira L. Lipase‐Catalysed Enzymatic Kinetic Resolution of Aromatic Morita‐Baylis‐Hillman Derivatives by Hydrolysis and Transesterification |
author_facet |
Mathebula, Nompumelelo P. Sheldon, Roger A. Bode, Moira L. |
author_sort |
Mathebula, Nompumelelo P. |
title |
Lipase‐Catalysed Enzymatic Kinetic Resolution of Aromatic Morita‐Baylis‐Hillman Derivatives by Hydrolysis and Transesterification |
title_short |
Lipase‐Catalysed Enzymatic Kinetic Resolution of Aromatic Morita‐Baylis‐Hillman Derivatives by Hydrolysis and Transesterification |
title_full |
Lipase‐Catalysed Enzymatic Kinetic Resolution of Aromatic Morita‐Baylis‐Hillman Derivatives by Hydrolysis and Transesterification |
title_fullStr |
Lipase‐Catalysed Enzymatic Kinetic Resolution of Aromatic Morita‐Baylis‐Hillman Derivatives by Hydrolysis and Transesterification |
title_full_unstemmed |
Lipase‐Catalysed Enzymatic Kinetic Resolution of Aromatic Morita‐Baylis‐Hillman Derivatives by Hydrolysis and Transesterification |
title_sort |
lipase‐catalysed enzymatic kinetic resolution of aromatic morita‐baylis‐hillman derivatives by hydrolysis and transesterification |
publisher |
Wiley |
publishDate |
2022 |
url |
http://dx.doi.org/10.1002/cbic.202200435 https://onlinelibrary.wiley.com/doi/pdf/10.1002/cbic.202200435 https://onlinelibrary.wiley.com/doi/full-xml/10.1002/cbic.202200435 |
genre |
Antarc* Antarctica |
genre_facet |
Antarc* Antarctica |
op_source |
ChemBioChem volume 23, issue 21 ISSN 1439-4227 1439-7633 |
op_rights |
http://creativecommons.org/licenses/by-nc/4.0/ |
op_doi |
https://doi.org/10.1002/cbic.202200435 |
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ChemBioChem |
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23 |
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21 |
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1810488750227062784 |