Lipase-mediated epoxidation of the cyclic monoterpene limonene to limonene oxide and limonene dioxide
S.1056-1060 Limonene is an industrially interesting monoterpene that accumulates in bulk quantities as by-product 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 chemi...
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ftfrauneprints:oai:publica.fraunhofer.de:publica/230341 2024-05-19T07:32:32+00:00 Lipase-mediated epoxidation of the cyclic monoterpene limonene to limonene oxide and limonene dioxide Wiemann, Lars O. Faltl, C. Sieber, V. 2012 https://publica.fraunhofer.de/handle/publica/230341 https://doi.org/10.5560/ZNB.2012-0167 en eng Zeitschrift für Naturforschung. B doi:10.5560/ZNB.2012-0167 https://publica.fraunhofer.de/handle/publica/230341 660 546 journal article 2012 ftfrauneprints https://doi.org/10.5560/ZNB.2012-0167 2024-04-24T00:09:22Z S.1056-1060 Limonene is an industrially interesting monoterpene that accumulates in bulk quantities as by-product 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 lipase-catalyzed 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 degrees 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 degrees C. For the first time we showed that it is possible to generate high amounts of limonene dioxide (similar to 30% with CalB on carrier 350 at 40 degrees 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. 67 Nr.10 Article in Journal/Newspaper Antarc* Antarctica Publikationsdatenbank der Fraunhofer-Gesellschaft Zeitschrift für Naturforschung B 67 10 1056 1060 |
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660 546 |
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660 546 Wiemann, Lars O. Faltl, C. Sieber, V. Lipase-mediated epoxidation of the cyclic monoterpene limonene to limonene oxide and limonene dioxide |
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660 546 |
description |
S.1056-1060 Limonene is an industrially interesting monoterpene that accumulates in bulk quantities as by-product 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 lipase-catalyzed 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 degrees 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 degrees C. For the first time we showed that it is possible to generate high amounts of limonene dioxide (similar to 30% with CalB on carrier 350 at 40 degrees 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. 67 Nr.10 |
format |
Article in Journal/Newspaper |
author |
Wiemann, Lars O. Faltl, C. Sieber, V. |
author_facet |
Wiemann, Lars O. Faltl, C. Sieber, V. |
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 |
publishDate |
2012 |
url |
https://publica.fraunhofer.de/handle/publica/230341 https://doi.org/10.5560/ZNB.2012-0167 |
genre |
Antarc* Antarctica |
genre_facet |
Antarc* Antarctica |
op_relation |
Zeitschrift für Naturforschung. B doi:10.5560/ZNB.2012-0167 https://publica.fraunhofer.de/handle/publica/230341 |
op_doi |
https://doi.org/10.5560/ZNB.2012-0167 |
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Zeitschrift für Naturforschung B |
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67 |
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10 |
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1056 |
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1060 |
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1799470630474612736 |