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Ionic Liquids: Efficient Media for the Lipase-Catalyzed Michael Addition
Recently, ionic liquids (ILs) have been regarded as ideal media for non-aqueous bio-catalysis. In this work, the synthesis of warfarin by the lipase-catalyzed Michael addition in IL media and the parameters that affected the warfarin yield were investigated. Experimental results demonstrated that th...
Autores principales: | , , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
MDPI
2018
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Materias: | |
Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6225191/ https://www.ncbi.nlm.nih.gov/pubmed/30150588 http://dx.doi.org/10.3390/molecules23092154 |
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author | Fan, Yunchang Cai, Dongxu Wang, Xin Yang, Lei |
author_facet | Fan, Yunchang Cai, Dongxu Wang, Xin Yang, Lei |
author_sort | Fan, Yunchang |
collection | PubMed |
description | Recently, ionic liquids (ILs) have been regarded as ideal media for non-aqueous bio-catalysis. In this work, the synthesis of warfarin by the lipase-catalyzed Michael addition in IL media and the parameters that affected the warfarin yield were investigated. Experimental results demonstrated that the chemical structures of the ILs were a major factor for influencing the warfarin yield. The ILs containing the NTf(2)(–) anion were suitable reaction media due to the high chemical stability of this anion. The incorporation of the hydroxyl group on the IL cation significantly improved the lipase activity due to the H(2)O-mimicking property of this group. The lipase activity decreased by increasing the alkyl chain length on the IL cation due to the non-polar domain formation of the IL cation at the active site entrance of lipase. The ILs and lipase could be reused no less than five times without reduction in the warfarin yield. |
format | Online Article Text |
id | pubmed-6225191 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2018 |
publisher | MDPI |
record_format | MEDLINE/PubMed |
spelling | pubmed-62251912018-11-13 Ionic Liquids: Efficient Media for the Lipase-Catalyzed Michael Addition Fan, Yunchang Cai, Dongxu Wang, Xin Yang, Lei Molecules Article Recently, ionic liquids (ILs) have been regarded as ideal media for non-aqueous bio-catalysis. In this work, the synthesis of warfarin by the lipase-catalyzed Michael addition in IL media and the parameters that affected the warfarin yield were investigated. Experimental results demonstrated that the chemical structures of the ILs were a major factor for influencing the warfarin yield. The ILs containing the NTf(2)(–) anion were suitable reaction media due to the high chemical stability of this anion. The incorporation of the hydroxyl group on the IL cation significantly improved the lipase activity due to the H(2)O-mimicking property of this group. The lipase activity decreased by increasing the alkyl chain length on the IL cation due to the non-polar domain formation of the IL cation at the active site entrance of lipase. The ILs and lipase could be reused no less than five times without reduction in the warfarin yield. MDPI 2018-08-27 /pmc/articles/PMC6225191/ /pubmed/30150588 http://dx.doi.org/10.3390/molecules23092154 Text en © 2018 by the authors. Licensee MDPI, Basel, Switzerland. This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution (CC BY) license (http://creativecommons.org/licenses/by/4.0/). |
spellingShingle | Article Fan, Yunchang Cai, Dongxu Wang, Xin Yang, Lei Ionic Liquids: Efficient Media for the Lipase-Catalyzed Michael Addition |
title | Ionic Liquids: Efficient Media for the Lipase-Catalyzed Michael Addition |
title_full | Ionic Liquids: Efficient Media for the Lipase-Catalyzed Michael Addition |
title_fullStr | Ionic Liquids: Efficient Media for the Lipase-Catalyzed Michael Addition |
title_full_unstemmed | Ionic Liquids: Efficient Media for the Lipase-Catalyzed Michael Addition |
title_short | Ionic Liquids: Efficient Media for the Lipase-Catalyzed Michael Addition |
title_sort | ionic liquids: efficient media for the lipase-catalyzed michael addition |
topic | Article |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6225191/ https://www.ncbi.nlm.nih.gov/pubmed/30150588 http://dx.doi.org/10.3390/molecules23092154 |
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