Kinetics of Enantiomerically Enriched Synthesis of Solketal Esters Using Native and SBA-15 supported P. Fluorescens Lipase
The studies showed that alkaline lipase from Pseudomonas fluorescens enables an irreversible transesterification of vinyl esters to give enantiomeric excess (eeR) of about 80% using vinyl butyrate as acyl donor and diisopropyl ether as a solvent, at partially optimized conditions. For the native lip...
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Polish Academy of Sciences Committee of Chemical and Process Engineering
2017-06-01
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| Series: | Chemical and Process Engineering |
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| Online Access: | http://www.degruyter.com/view/j/cpe.2017.38.issue-2/cpe-2017-0016/cpe-2017-0016.xml?format=INT |
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| author | Zniszczoł Aurelia Szymańska Katarzyna Kocurek Jacek Bryjak Jolanta Walczak Krzysztof Jarzębski Andrzej |
| author_facet | Zniszczoł Aurelia Szymańska Katarzyna Kocurek Jacek Bryjak Jolanta Walczak Krzysztof Jarzębski Andrzej |
| author_sort | Zniszczoł Aurelia |
| collection | DOAJ |
| description | The studies showed that alkaline lipase from Pseudomonas fluorescens enables an irreversible transesterification of vinyl esters to give enantiomeric excess (eeR) of about 80% using vinyl butyrate as acyl donor and diisopropyl ether as a solvent, at partially optimized conditions. For the native lipase the process was adequately described by a five-parameter Ping-Pong Bi Bi model for both enantiomers plus expression accounting for the formation of enzyme-acyl donor complex, but for the same lipase supported on mesoporous materials of SBA-15-Oc type, R-product inhibition also had to be taken into account. The use of hydrophobic support increased by more than two-fold the rate of the S-solketal conversion but even more that of R-solketal. Thus the immobilization of lipase had very positive effect on the process kinetics but decreased its enantioselectivity. |
| format | Article |
| id | doaj-art-70fe5d998b014d05ad206f47da6caeeb |
| institution | DOAJ |
| issn | 2300-1925 |
| language | English |
| publishDate | 2017-06-01 |
| publisher | Polish Academy of Sciences Committee of Chemical and Process Engineering |
| record_format | Article |
| series | Chemical and Process Engineering |
| spelling | doaj-art-70fe5d998b014d05ad206f47da6caeeb2025-08-20T03:10:01ZengPolish Academy of Sciences Committee of Chemical and Process EngineeringChemical and Process Engineering2300-19252017-06-0138220921510.1515/cpe-2017-0016cpe-2017-0016Kinetics of Enantiomerically Enriched Synthesis of Solketal Esters Using Native and SBA-15 supported P. Fluorescens LipaseZniszczoł Aurelia0Szymańska Katarzyna1Kocurek Jacek2Bryjak Jolanta3Walczak Krzysztof4Jarzębski Andrzej5Department of Chemical Engineering and Process Design, Silesian University of Technology, 44-100 Gliwice, Ks. M. Strzody 7, Gliwice, PolandDepartment of Chemical Engineering and Process Design, Silesian University of Technology, 44-100 Gliwice, Ks. M. Strzody 7, Gliwice, PolandDepartment of Chemical Engineering and Process Design, Silesian University of Technology, 44-100 Gliwice, Ks. M. Strzody 7, Gliwice, PolandDepartment of Bioroganic Chemistry, Faculty of Chemistry, Wrocław University of Technology, 50-370 Wrocław, Wybrzeże Wyspiańskiego 27, Wrocław, PolandDepartment of Chemical Engineering and Process Design, Silesian University of Technology, 44-100 Gliwice, Ks. M. Strzody 7, Gliwice, PolandDepartment of Chemical Engineering and Process Design, Silesian University of Technology, 44-100 Gliwice, Ks. M. Strzody 7, Gliwice, PolandThe studies showed that alkaline lipase from Pseudomonas fluorescens enables an irreversible transesterification of vinyl esters to give enantiomeric excess (eeR) of about 80% using vinyl butyrate as acyl donor and diisopropyl ether as a solvent, at partially optimized conditions. For the native lipase the process was adequately described by a five-parameter Ping-Pong Bi Bi model for both enantiomers plus expression accounting for the formation of enzyme-acyl donor complex, but for the same lipase supported on mesoporous materials of SBA-15-Oc type, R-product inhibition also had to be taken into account. The use of hydrophobic support increased by more than two-fold the rate of the S-solketal conversion but even more that of R-solketal. Thus the immobilization of lipase had very positive effect on the process kinetics but decreased its enantioselectivity.http://www.degruyter.com/view/j/cpe.2017.38.issue-2/cpe-2017-0016/cpe-2017-0016.xml?format=INTbioenantioselectivitysolketalping-pong kineticstransesterification |
| spellingShingle | Zniszczoł Aurelia Szymańska Katarzyna Kocurek Jacek Bryjak Jolanta Walczak Krzysztof Jarzębski Andrzej Kinetics of Enantiomerically Enriched Synthesis of Solketal Esters Using Native and SBA-15 supported P. Fluorescens Lipase Chemical and Process Engineering bioenantioselectivity solketal ping-pong kinetics transesterification |
| title | Kinetics of Enantiomerically Enriched Synthesis of Solketal Esters Using Native and SBA-15 supported P. Fluorescens Lipase |
| title_full | Kinetics of Enantiomerically Enriched Synthesis of Solketal Esters Using Native and SBA-15 supported P. Fluorescens Lipase |
| title_fullStr | Kinetics of Enantiomerically Enriched Synthesis of Solketal Esters Using Native and SBA-15 supported P. Fluorescens Lipase |
| title_full_unstemmed | Kinetics of Enantiomerically Enriched Synthesis of Solketal Esters Using Native and SBA-15 supported P. Fluorescens Lipase |
| title_short | Kinetics of Enantiomerically Enriched Synthesis of Solketal Esters Using Native and SBA-15 supported P. Fluorescens Lipase |
| title_sort | kinetics of enantiomerically enriched synthesis of solketal esters using native and sba 15 supported p fluorescens lipase |
| topic | bioenantioselectivity solketal ping-pong kinetics transesterification |
| url | http://www.degruyter.com/view/j/cpe.2017.38.issue-2/cpe-2017-0016/cpe-2017-0016.xml?format=INT |
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