Highly Efficient Enzymatic Synthesis of 2‐Monoacylglycerides and Structured Lipids and their Production on a Technical Scale
Abstract We report here a two‐step process for the high‐yield enzymatic synthesis of 2‐monoacylglycerides (2‐MAG) of saturated as well as unsaturated fatty acids with different chain lengths. The process consists of two steps: first the unselective esterification of fatty acids and glycerol leading...
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Online Access: | http://dx.doi.org/10.1007/s11745-007-3084-y https://onlinelibrary.wiley.com/doi/full/10.1007/s11745-007-3084-y |
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crwiley:10.1007/s11745-007-3084-y 2024-09-15T17:42:09+00:00 Highly Efficient Enzymatic Synthesis of 2‐Monoacylglycerides and Structured Lipids and their Production on a Technical Scale Pfeffer, Jan Freund, Andreas Bel‐Rhlid, Rachid Hansen, Carl‐Erik Reuss, Matthias Schmid, Rolf D. Maurer, Steffen C. 2007 http://dx.doi.org/10.1007/s11745-007-3084-y https://onlinelibrary.wiley.com/doi/full/10.1007/s11745-007-3084-y en eng Wiley http://onlinelibrary.wiley.com/termsAndConditions#vor Lipids volume 42, issue 10 ISSN 0024-4201 1558-9307 journal-article 2007 crwiley https://doi.org/10.1007/s11745-007-3084-y 2024-07-30T04:18:55Z Abstract We report here a two‐step process for the high‐yield enzymatic synthesis of 2‐monoacylglycerides (2‐MAG) of saturated as well as unsaturated fatty acids with different chain lengths. The process consists of two steps: first the unselective esterification of fatty acids and glycerol leading to a triacylglyceride followed by an sn 1,3‐selective alcoholysis reaction yielding 2‐monoacylglycerides. Remarkably, both steps can be catalyzed by lipase B from Candida antarctica (CalB). The whole process including esterification and alcoholysis was scaled up in a miniplant to a total volume of 10 l. With this volume, a two‐step process catalyzed by CalB for the synthesis of 1,3‐oleoyl‐2‐palmitoylglycerol (OPO) using tripalmitate as starting material was established. On a laboratory scale, we obtained gram quantities of the synthesized 2‐monoacylglycerides of polyunsaturated fatty acids such as arachidonic‐, docosahexaenoic‐ and eicosapentaenoic acids and up to 96.4% of the theoretically possible yield with 95% purity. On a technical scale (>100 g of product, >5 l of reaction volume), 97% yield was reached in the esterification and 73% in the alcoholysis and a new promising process for the enzymatic synthesis of OPO was established. Article in Journal/Newspaper Antarc* Antarctica Wiley Online Library Lipids 42 10 |
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Wiley Online Library |
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language |
English |
description |
Abstract We report here a two‐step process for the high‐yield enzymatic synthesis of 2‐monoacylglycerides (2‐MAG) of saturated as well as unsaturated fatty acids with different chain lengths. The process consists of two steps: first the unselective esterification of fatty acids and glycerol leading to a triacylglyceride followed by an sn 1,3‐selective alcoholysis reaction yielding 2‐monoacylglycerides. Remarkably, both steps can be catalyzed by lipase B from Candida antarctica (CalB). The whole process including esterification and alcoholysis was scaled up in a miniplant to a total volume of 10 l. With this volume, a two‐step process catalyzed by CalB for the synthesis of 1,3‐oleoyl‐2‐palmitoylglycerol (OPO) using tripalmitate as starting material was established. On a laboratory scale, we obtained gram quantities of the synthesized 2‐monoacylglycerides of polyunsaturated fatty acids such as arachidonic‐, docosahexaenoic‐ and eicosapentaenoic acids and up to 96.4% of the theoretically possible yield with 95% purity. On a technical scale (>100 g of product, >5 l of reaction volume), 97% yield was reached in the esterification and 73% in the alcoholysis and a new promising process for the enzymatic synthesis of OPO was established. |
format |
Article in Journal/Newspaper |
author |
Pfeffer, Jan Freund, Andreas Bel‐Rhlid, Rachid Hansen, Carl‐Erik Reuss, Matthias Schmid, Rolf D. Maurer, Steffen C. |
spellingShingle |
Pfeffer, Jan Freund, Andreas Bel‐Rhlid, Rachid Hansen, Carl‐Erik Reuss, Matthias Schmid, Rolf D. Maurer, Steffen C. Highly Efficient Enzymatic Synthesis of 2‐Monoacylglycerides and Structured Lipids and their Production on a Technical Scale |
author_facet |
Pfeffer, Jan Freund, Andreas Bel‐Rhlid, Rachid Hansen, Carl‐Erik Reuss, Matthias Schmid, Rolf D. Maurer, Steffen C. |
author_sort |
Pfeffer, Jan |
title |
Highly Efficient Enzymatic Synthesis of 2‐Monoacylglycerides and Structured Lipids and their Production on a Technical Scale |
title_short |
Highly Efficient Enzymatic Synthesis of 2‐Monoacylglycerides and Structured Lipids and their Production on a Technical Scale |
title_full |
Highly Efficient Enzymatic Synthesis of 2‐Monoacylglycerides and Structured Lipids and their Production on a Technical Scale |
title_fullStr |
Highly Efficient Enzymatic Synthesis of 2‐Monoacylglycerides and Structured Lipids and their Production on a Technical Scale |
title_full_unstemmed |
Highly Efficient Enzymatic Synthesis of 2‐Monoacylglycerides and Structured Lipids and their Production on a Technical Scale |
title_sort |
highly efficient enzymatic synthesis of 2‐monoacylglycerides and structured lipids and their production on a technical scale |
publisher |
Wiley |
publishDate |
2007 |
url |
http://dx.doi.org/10.1007/s11745-007-3084-y https://onlinelibrary.wiley.com/doi/full/10.1007/s11745-007-3084-y |
genre |
Antarc* Antarctica |
genre_facet |
Antarc* Antarctica |
op_source |
Lipids volume 42, issue 10 ISSN 0024-4201 1558-9307 |
op_rights |
http://onlinelibrary.wiley.com/termsAndConditions#vor |
op_doi |
https://doi.org/10.1007/s11745-007-3084-y |
container_title |
Lipids |
container_volume |
42 |
container_issue |
10 |
_version_ |
1810488593855021056 |