Lipase-mediated Epoxidation of the Cyclic Monoterpene Limonene to Limonene Oxide and Limonene Dioxide
Limonene is an industrially interesting monoterpene that accumulates in bulk quantities as byproduct of the fruit juice industry. The corresponding epoxides are versatile synthetic intermediates and additives for the chemical industry. Due to a number of disadvantages of classical chemical epoxidati...
Published in: | Zeitschrift für Naturforschung B |
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Language: | English |
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Walter de Gruyter GmbH
2012
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Online Access: | http://dx.doi.org/10.5560/znb.2012-0167 http://www.degruyter.com/view/j/znb.2012.67.issue-10/znb.2012-0167/znb.2012-0167.xml https://www.degruyter.com/document/doi/10.5560/znb.2012-0167/xml https://www.degruyter.com/document/doi/10.5560/znb.2012-0167/pdf |
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crdegruyter:10.5560/znb.2012-0167 2024-09-15T17:46:09+00:00 Lipase-mediated Epoxidation of the Cyclic Monoterpene Limonene to Limonene Oxide and Limonene Dioxide Wiemann, Lars O. Faltl, Christina Sieber, Volker 2012 http://dx.doi.org/10.5560/znb.2012-0167 http://www.degruyter.com/view/j/znb.2012.67.issue-10/znb.2012-0167/znb.2012-0167.xml https://www.degruyter.com/document/doi/10.5560/znb.2012-0167/xml https://www.degruyter.com/document/doi/10.5560/znb.2012-0167/pdf en eng Walter de Gruyter GmbH http://creativecommons.org/licenses/by-nc-nd/3.0/ Zeitschrift für Naturforschung B volume 67, issue 10, page 1056-1060 ISSN 1865-7117 0932-0776 journal-article 2012 crdegruyter https://doi.org/10.5560/znb.2012-0167 2024-07-22T04:11:32Z Limonene is an industrially interesting monoterpene that accumulates in bulk quantities as byproduct of the fruit juice industry. The corresponding epoxides are versatile synthetic intermediates and additives for the chemical industry. Due to a number of disadvantages of classical chemical epoxidation including serious safety issues and unwanted side-reactions, we here used a mild lipasecatalyzed chemo-enzymatic epoxidation system, with either free or different immobilized forms of Candida antarctica lipase B. Full limonene conversion (> 98%) was easily achieved at 40°C within less than 24 h. The enzymatic activities in the formation of limonene monoxide significantly varied from either 1 - 3:4 U/mg biocatalyst at r. t. or from 1.7 - 4:9 U/mg biocatalyst at 40°C. For the first time we showed that it is possible to generate high amounts of limonene dioxide ( ~ 30% with CalB on carrier 350 at 40°C) using this mild lipase-mediated epoxidation method. Enzyme activities and limonene dioxide yields strongly depend on the nature of the selected enzyme carrier, the immobilization method and the reaction temperature. Article in Journal/Newspaper Antarc* Antarctica De Gruyter Zeitschrift für Naturforschung B 67 10 1056 1060 |
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Open Polar |
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De Gruyter |
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crdegruyter |
language |
English |
description |
Limonene is an industrially interesting monoterpene that accumulates in bulk quantities as byproduct of the fruit juice industry. The corresponding epoxides are versatile synthetic intermediates and additives for the chemical industry. Due to a number of disadvantages of classical chemical epoxidation including serious safety issues and unwanted side-reactions, we here used a mild lipasecatalyzed chemo-enzymatic epoxidation system, with either free or different immobilized forms of Candida antarctica lipase B. Full limonene conversion (> 98%) was easily achieved at 40°C within less than 24 h. The enzymatic activities in the formation of limonene monoxide significantly varied from either 1 - 3:4 U/mg biocatalyst at r. t. or from 1.7 - 4:9 U/mg biocatalyst at 40°C. For the first time we showed that it is possible to generate high amounts of limonene dioxide ( ~ 30% with CalB on carrier 350 at 40°C) using this mild lipase-mediated epoxidation method. Enzyme activities and limonene dioxide yields strongly depend on the nature of the selected enzyme carrier, the immobilization method and the reaction temperature. |
format |
Article in Journal/Newspaper |
author |
Wiemann, Lars O. Faltl, Christina Sieber, Volker |
spellingShingle |
Wiemann, Lars O. Faltl, Christina Sieber, Volker Lipase-mediated Epoxidation of the Cyclic Monoterpene Limonene to Limonene Oxide and Limonene Dioxide |
author_facet |
Wiemann, Lars O. Faltl, Christina Sieber, Volker |
author_sort |
Wiemann, Lars O. |
title |
Lipase-mediated Epoxidation of the Cyclic Monoterpene Limonene to Limonene Oxide and Limonene Dioxide |
title_short |
Lipase-mediated Epoxidation of the Cyclic Monoterpene Limonene to Limonene Oxide and Limonene Dioxide |
title_full |
Lipase-mediated Epoxidation of the Cyclic Monoterpene Limonene to Limonene Oxide and Limonene Dioxide |
title_fullStr |
Lipase-mediated Epoxidation of the Cyclic Monoterpene Limonene to Limonene Oxide and Limonene Dioxide |
title_full_unstemmed |
Lipase-mediated Epoxidation of the Cyclic Monoterpene Limonene to Limonene Oxide and Limonene Dioxide |
title_sort |
lipase-mediated epoxidation of the cyclic monoterpene limonene to limonene oxide and limonene dioxide |
publisher |
Walter de Gruyter GmbH |
publishDate |
2012 |
url |
http://dx.doi.org/10.5560/znb.2012-0167 http://www.degruyter.com/view/j/znb.2012.67.issue-10/znb.2012-0167/znb.2012-0167.xml https://www.degruyter.com/document/doi/10.5560/znb.2012-0167/xml https://www.degruyter.com/document/doi/10.5560/znb.2012-0167/pdf |
genre |
Antarc* Antarctica |
genre_facet |
Antarc* Antarctica |
op_source |
Zeitschrift für Naturforschung B volume 67, issue 10, page 1056-1060 ISSN 1865-7117 0932-0776 |
op_rights |
http://creativecommons.org/licenses/by-nc-nd/3.0/ |
op_doi |
https://doi.org/10.5560/znb.2012-0167 |
container_title |
Zeitschrift für Naturforschung B |
container_volume |
67 |
container_issue |
10 |
container_start_page |
1056 |
op_container_end_page |
1060 |
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1810494136513462272 |