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Mar. Drugs 2015, 13(1), 173-201; doi:10.3390/md13010173

Synthesis of Enantiopure Reversed Structured Ether Lipids of the 1-O-Alkyl-sn-2,3-diacylglycerol Type

Science Institute, University of Iceland, Dunhaga 3, 107 Reykjavik, Iceland
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Author to whom correspondence should be addressed.
Academic Editors: Orazio Taglialatela-Scafati and Yoshihide Usami
Received: 22 October 2014 / Accepted: 17 December 2014 / Published: 7 January 2015
(This article belongs to the Special Issue Synthesis around Marine Natural Products)
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Abstract

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. View Full-Text
Keywords: diacylglyceryl ethers (DAGE); ether lipids; structured lipids; n-3 PUFA; EPA; DHA; n-3 PUFA oxime esters; lipase; chemoenzymatic synthesis; focused lipid library diacylglyceryl ethers (DAGE); ether lipids; structured lipids; n-3 PUFA; EPA; DHA; n-3 PUFA oxime esters; lipase; chemoenzymatic synthesis; focused lipid library
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This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. (CC BY 4.0).

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MDPI and ACS Style

Magnusson, C.D.; Gudmundsdottir, A.V.; Hansen, K.-A.; Haraldsson, G.G. Synthesis of Enantiopure Reversed Structured Ether Lipids of the 1-O-Alkyl-sn-2,3-diacylglycerol Type. Mar. Drugs 2015, 13, 173-201.

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