Synthesis of Enantiopure Reversed Structured Ether Lipids of the 1-O-Alkyl-sn-2,3-diacylglycerol Type
| Autor: | Kai-Anders Hansen, Carlos D. Magnusson, Anna V. Gudmundsdottir, Gudmundur G. Haraldsson |
|---|---|
| Jazyk: | angličtina |
| Rok vydání: | 2015 |
| Předmět: |
n-3 PUFA oxime esters
Magnetic Resonance Spectroscopy Pharmaceutical Science Ether Article n-3 PUFA focused lipid library Diglycerides chemistry.chemical_compound Drug Discovery lipase Organic chemistry structured lipids Lipase ether lipids Pharmacology Toxicology and Pharmaceutics (miscellaneous) lcsh:QH301-705.5 chemistry.chemical_classification biology Chemistry Phospholipid Ethers Fatty acid Stereoisomerism EPA chemoenzymatic synthesis Oxime biology.organism_classification diacylglyceryl ethers (DAGE) DHA Enantiopure drug lcsh:Biology (General) biology.protein Candida antarctica lipids (amino acids peptides and proteins) Enantiomer |
| Zdroj: | Marine Drugs, Vol 13, Iss 1, Pp 173-201 (2015) Marine Drugs Volume 13 Issue 1 Pages 173-201 |
| ISSN: | 1660-3397 |
| Popis: | 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. |
| Databáze: | OpenAIRE |
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