Utilization of reaction medium‐dependent regiospecificity of Candida antarctica lipase (Novozym 435) for the synthesis of 1,3‐dicapryloyl‐2‐docosahexaenoyl (or eicosapentaenoyl) glycerol
Abstract A highly efficient enzymatic method for the synthesis of regioisomerically pure 1,3‐dicapryloyl‐2‐docosahexaenoyl glycerol (CDC) in two steps was established. 2‐Monoglyceride (2‐MG) formation by ethanolysis of tridocosahexaenoylglycerol (DDD) with immobilized Candida antarctica lipase (Novo...
Published in: | Journal of the American Oil Chemists' Society |
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crwiley:10.1007/s11746-001-0258-3 2024-09-15T17:48:04+00:00 Utilization of reaction medium‐dependent regiospecificity of Candida antarctica lipase (Novozym 435) for the synthesis of 1,3‐dicapryloyl‐2‐docosahexaenoyl (or eicosapentaenoyl) glycerol Irimescu, Roxana Furihata, Kiyomi Hata, Kazuhiko Iwasaki, Yugo Yamane, Tsuneo 2001 http://dx.doi.org/10.1007/s11746-001-0258-3 https://onlinelibrary.wiley.com/doi/full/10.1007/s11746-001-0258-3 en eng Wiley http://onlinelibrary.wiley.com/termsAndConditions#vor Journal of the American Oil Chemists' Society volume 78, issue 3, page 285-290 ISSN 0003-021X 1558-9331 journal-article 2001 crwiley https://doi.org/10.1007/s11746-001-0258-3 2024-07-30T04:18:47Z Abstract A highly efficient enzymatic method for the synthesis of regioisomerically pure 1,3‐dicapryloyl‐2‐docosahexaenoyl glycerol (CDC) in two steps was established. 2‐Monoglyceride (2‐MG) formation by ethanolysis of tridocosahexaenoylglycerol (DDD) with immobilized Candida antarctica lipase (Novozym 435) as catalyst was the key step of the synthesis. CDC was finally obtained by reesterification of 2‐MG with ethylcaprylate (EtC) catalyzed by Rhizomucor miehei lipase (Lipozyme IM). The regiospecificity of Novozym 435 depended on the type of reaction and the initial composition of the reaction medium. It displayed strict 1,3‐regiospecificity for ethanolysis at a high excess of ethanol in the reaction mixture although it displayed no regiospecificity in transesterification and esterification reactions. The highest yield of CDC (85.4%) was obtained by ethanolysis at a 4∶1 weight ratio of ethanol/DDD for 6 h followed by reesterification at a 20∶1 molar ratio of EtC/initial DDD for 1.5 h. The regioisomeric purity of CDC was 100%. Good results were obtained also for the synthesis of 1,3‐dicapryloyl‐eicosapentaenoylglycerol (CEC) by the same method: 84.2% yield and 99.8% regioisomeric purity at the same reactant ratios as above. The yield of the reesterification step and the regioisomeric purity of the product were influenced by the molar ratio of the reactants for both CDC and CEC syntheses: higher excess of EtC favored higher yields and regioisomeric purity of the products. Article in Journal/Newspaper Antarc* Antarctica Wiley Online Library Journal of the American Oil Chemists' Society 78 3 285 290 |
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Open Polar |
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Wiley Online Library |
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crwiley |
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English |
description |
Abstract A highly efficient enzymatic method for the synthesis of regioisomerically pure 1,3‐dicapryloyl‐2‐docosahexaenoyl glycerol (CDC) in two steps was established. 2‐Monoglyceride (2‐MG) formation by ethanolysis of tridocosahexaenoylglycerol (DDD) with immobilized Candida antarctica lipase (Novozym 435) as catalyst was the key step of the synthesis. CDC was finally obtained by reesterification of 2‐MG with ethylcaprylate (EtC) catalyzed by Rhizomucor miehei lipase (Lipozyme IM). The regiospecificity of Novozym 435 depended on the type of reaction and the initial composition of the reaction medium. It displayed strict 1,3‐regiospecificity for ethanolysis at a high excess of ethanol in the reaction mixture although it displayed no regiospecificity in transesterification and esterification reactions. The highest yield of CDC (85.4%) was obtained by ethanolysis at a 4∶1 weight ratio of ethanol/DDD for 6 h followed by reesterification at a 20∶1 molar ratio of EtC/initial DDD for 1.5 h. The regioisomeric purity of CDC was 100%. Good results were obtained also for the synthesis of 1,3‐dicapryloyl‐eicosapentaenoylglycerol (CEC) by the same method: 84.2% yield and 99.8% regioisomeric purity at the same reactant ratios as above. The yield of the reesterification step and the regioisomeric purity of the product were influenced by the molar ratio of the reactants for both CDC and CEC syntheses: higher excess of EtC favored higher yields and regioisomeric purity of the products. |
format |
Article in Journal/Newspaper |
author |
Irimescu, Roxana Furihata, Kiyomi Hata, Kazuhiko Iwasaki, Yugo Yamane, Tsuneo |
spellingShingle |
Irimescu, Roxana Furihata, Kiyomi Hata, Kazuhiko Iwasaki, Yugo Yamane, Tsuneo Utilization of reaction medium‐dependent regiospecificity of Candida antarctica lipase (Novozym 435) for the synthesis of 1,3‐dicapryloyl‐2‐docosahexaenoyl (or eicosapentaenoyl) glycerol |
author_facet |
Irimescu, Roxana Furihata, Kiyomi Hata, Kazuhiko Iwasaki, Yugo Yamane, Tsuneo |
author_sort |
Irimescu, Roxana |
title |
Utilization of reaction medium‐dependent regiospecificity of Candida antarctica lipase (Novozym 435) for the synthesis of 1,3‐dicapryloyl‐2‐docosahexaenoyl (or eicosapentaenoyl) glycerol |
title_short |
Utilization of reaction medium‐dependent regiospecificity of Candida antarctica lipase (Novozym 435) for the synthesis of 1,3‐dicapryloyl‐2‐docosahexaenoyl (or eicosapentaenoyl) glycerol |
title_full |
Utilization of reaction medium‐dependent regiospecificity of Candida antarctica lipase (Novozym 435) for the synthesis of 1,3‐dicapryloyl‐2‐docosahexaenoyl (or eicosapentaenoyl) glycerol |
title_fullStr |
Utilization of reaction medium‐dependent regiospecificity of Candida antarctica lipase (Novozym 435) for the synthesis of 1,3‐dicapryloyl‐2‐docosahexaenoyl (or eicosapentaenoyl) glycerol |
title_full_unstemmed |
Utilization of reaction medium‐dependent regiospecificity of Candida antarctica lipase (Novozym 435) for the synthesis of 1,3‐dicapryloyl‐2‐docosahexaenoyl (or eicosapentaenoyl) glycerol |
title_sort |
utilization of reaction medium‐dependent regiospecificity of candida antarctica lipase (novozym 435) for the synthesis of 1,3‐dicapryloyl‐2‐docosahexaenoyl (or eicosapentaenoyl) glycerol |
publisher |
Wiley |
publishDate |
2001 |
url |
http://dx.doi.org/10.1007/s11746-001-0258-3 https://onlinelibrary.wiley.com/doi/full/10.1007/s11746-001-0258-3 |
genre |
Antarc* Antarctica |
genre_facet |
Antarc* Antarctica |
op_source |
Journal of the American Oil Chemists' Society volume 78, issue 3, page 285-290 ISSN 0003-021X 1558-9331 |
op_rights |
http://onlinelibrary.wiley.com/termsAndConditions#vor |
op_doi |
https://doi.org/10.1007/s11746-001-0258-3 |
container_title |
Journal of the American Oil Chemists' Society |
container_volume |
78 |
container_issue |
3 |
container_start_page |
285 |
op_container_end_page |
290 |
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1810288944103817216 |