Synthesis of Enantiopure Reversed Structured Ether Lipids of the 1-O-Alkyl-sn-2,3-diacylglycerol Type
This report describes the synthesis of reversed structured 1-O-alkyl-2,3-diacyl-sn-glycerols (DAGEs) possessing a pure saturated even number fatty acid (C6:0–C16:0) at the sn-2 position along with a pure EPA or DHA located at the terminal sn-3 position of the glycerol backbone of chimyl, batyl and s...
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ftdoajarticles:oai:doaj.org/article:68a7015f1b574d0ab0ce29b85537b485 2023-05-15T14:04:55+02:00 Synthesis of Enantiopure Reversed Structured Ether Lipids of the 1-O-Alkyl-sn-2,3-diacylglycerol Type Carlos D. Magnusson Anna V. Gudmundsdottir Kai-Anders Hansen Gudmundur G. Haraldsson 2015-01-01T00:00:00Z https://doi.org/10.3390/md13010173 https://doaj.org/article/68a7015f1b574d0ab0ce29b85537b485 EN eng MDPI AG http://www.mdpi.com/1660-3397/13/1/173 https://doaj.org/toc/1660-3397 1660-3397 doi:10.3390/md13010173 https://doaj.org/article/68a7015f1b574d0ab0ce29b85537b485 Marine Drugs, Vol 13, Iss 1, Pp 173-201 (2015) diacylglyceryl ethers (DAGE) ether lipids structured lipids n-3 PUFA EPA DHA n-3 PUFA oxime esters lipase chemoenzymatic synthesis focused lipid library Biology (General) QH301-705.5 article 2015 ftdoajarticles https://doi.org/10.3390/md13010173 2022-12-30T19:56:59Z This report describes the synthesis of reversed structured 1-O-alkyl-2,3-diacyl-sn-glycerols (DAGEs) possessing a pure saturated even number fatty acid (C6:0–C16:0) at the sn-2 position along with a pure EPA or DHA located at the terminal sn-3 position of the glycerol backbone of chimyl, batyl and selachyl alcohols. These adducts were synthesized by a highly efficient two-step chemoenzymatic process involving an immobilized Candida antarctica lipase to introduce pure EPA and DHA activated as oxime esters exclusively to the sn-3 terminal position of enantiopure chimyl, batyl and selachyl alcohols in excellent yields. The saturated fatty acids were subsequently incorporated to the remaining sn-2 position of the resulting 3-monoacylglyceryl ethers (3-MAGEs) using EDAC coupling agent in the presence of DMAP in very high to excellent yields (85%–98%). No losses of enantiomeric composition were observed during these processes. The multiple utilities of the resulting focused library of reversed structured DAGEs are discussed including how such compounds may possibly be utilized within the pharmaceutical area. Article in Journal/Newspaper Antarc* Antarctica Directory of Open Access Journals: DOAJ Articles Marine Drugs 13 1 173 201 |
institution |
Open Polar |
collection |
Directory of Open Access Journals: DOAJ Articles |
op_collection_id |
ftdoajarticles |
language |
English |
topic |
diacylglyceryl ethers (DAGE) ether lipids structured lipids n-3 PUFA EPA DHA n-3 PUFA oxime esters lipase chemoenzymatic synthesis focused lipid library Biology (General) QH301-705.5 |
spellingShingle |
diacylglyceryl ethers (DAGE) ether lipids structured lipids n-3 PUFA EPA DHA n-3 PUFA oxime esters lipase chemoenzymatic synthesis focused lipid library Biology (General) QH301-705.5 Carlos D. Magnusson Anna V. Gudmundsdottir Kai-Anders Hansen Gudmundur G. Haraldsson Synthesis of Enantiopure Reversed Structured Ether Lipids of the 1-O-Alkyl-sn-2,3-diacylglycerol Type |
topic_facet |
diacylglyceryl ethers (DAGE) ether lipids structured lipids n-3 PUFA EPA DHA n-3 PUFA oxime esters lipase chemoenzymatic synthesis focused lipid library Biology (General) QH301-705.5 |
description |
This report describes the synthesis of reversed structured 1-O-alkyl-2,3-diacyl-sn-glycerols (DAGEs) possessing a pure saturated even number fatty acid (C6:0–C16:0) at the sn-2 position along with a pure EPA or DHA located at the terminal sn-3 position of the glycerol backbone of chimyl, batyl and selachyl alcohols. These adducts were synthesized by a highly efficient two-step chemoenzymatic process involving an immobilized Candida antarctica lipase to introduce pure EPA and DHA activated as oxime esters exclusively to the sn-3 terminal position of enantiopure chimyl, batyl and selachyl alcohols in excellent yields. The saturated fatty acids were subsequently incorporated to the remaining sn-2 position of the resulting 3-monoacylglyceryl ethers (3-MAGEs) using EDAC coupling agent in the presence of DMAP in very high to excellent yields (85%–98%). No losses of enantiomeric composition were observed during these processes. The multiple utilities of the resulting focused library of reversed structured DAGEs are discussed including how such compounds may possibly be utilized within the pharmaceutical area. |
format |
Article in Journal/Newspaper |
author |
Carlos D. Magnusson Anna V. Gudmundsdottir Kai-Anders Hansen Gudmundur G. Haraldsson |
author_facet |
Carlos D. Magnusson Anna V. Gudmundsdottir Kai-Anders Hansen Gudmundur G. Haraldsson |
author_sort |
Carlos D. Magnusson |
title |
Synthesis of Enantiopure Reversed Structured Ether Lipids of the 1-O-Alkyl-sn-2,3-diacylglycerol Type |
title_short |
Synthesis of Enantiopure Reversed Structured Ether Lipids of the 1-O-Alkyl-sn-2,3-diacylglycerol Type |
title_full |
Synthesis of Enantiopure Reversed Structured Ether Lipids of the 1-O-Alkyl-sn-2,3-diacylglycerol Type |
title_fullStr |
Synthesis of Enantiopure Reversed Structured Ether Lipids of the 1-O-Alkyl-sn-2,3-diacylglycerol Type |
title_full_unstemmed |
Synthesis of Enantiopure Reversed Structured Ether Lipids of the 1-O-Alkyl-sn-2,3-diacylglycerol Type |
title_sort |
synthesis of enantiopure reversed structured ether lipids of the 1-o-alkyl-sn-2,3-diacylglycerol type |
publisher |
MDPI AG |
publishDate |
2015 |
url |
https://doi.org/10.3390/md13010173 https://doaj.org/article/68a7015f1b574d0ab0ce29b85537b485 |
genre |
Antarc* Antarctica |
genre_facet |
Antarc* Antarctica |
op_source |
Marine Drugs, Vol 13, Iss 1, Pp 173-201 (2015) |
op_relation |
http://www.mdpi.com/1660-3397/13/1/173 https://doaj.org/toc/1660-3397 1660-3397 doi:10.3390/md13010173 https://doaj.org/article/68a7015f1b574d0ab0ce29b85537b485 |
op_doi |
https://doi.org/10.3390/md13010173 |
container_title |
Marine Drugs |
container_volume |
13 |
container_issue |
1 |
container_start_page |
173 |
op_container_end_page |
201 |
_version_ |
1766276366958854144 |