Structure of an ether phospholipid. Note ether at first and second positions.Plasmalogen. Note ether at first position, and ester at second position.Platelet-activating factor. Note ether at first position, and acyl group at second position.
In biochemistry, an ether lipid refers to any lipid in which the lipid "tail" group is attached to the glycerol backbone via an ether bond at any position. In contrast, conventional glycerophospholipids and triglycerides are triesters.[1] Structural types include:
Ether phospholipids: phospholipids are known to have ether-linked "tails" instead of the usual ester linkage.[1]
Ether on sn-1, ester on sn-2: "ether lipids" in the context of bacteria and eukaryotes refer to this class of lipids. Compared to the usual 1,2-diacyl-sn-glycerol (DAG), the sn-1 linkage is replaced with an ester bond.[1][2][3]
Based on whether the sn-1 lipid is unsaturated next to the ether linkage, they can be further divided into alkenyl-acylphospholipids ("plasmenylphospholipid", 1-0-alk-1’-enyl-2-acyl-sn-glycerol) and alkyl-acylphospholipids ("plasmanylphospholipid"). This class of lipids have important roles in human cell signaling and structure.[4]
Ether on sn-2 and sn-3: this class with flipped chirality on the phosphate connection is called an "archaeal ether lipid". With few (if any) exceptions, it is only found among archaea. The part excluding the phoshphate group is known as archaeol.[5][6]
Ether analogues of triglycerides: 1-alkyldiacyl-sn-glycerols (alkyldiacylglycerols) are found in significant proportions in marine animals.[5]
Other ether lipids: a number of other lipids not belonging to any of the classes above contain the ether linkage. For example, seminolipid, a vital part of the testes and sperm cells, has a ether linkage.[1]
The term "plasmalogen" can refer to any ether lipid with a vinyl ether linkage, i.e. ones with a carbon-carbon double bond next to the ether linkage. Without specification it generally refers to alkenyl-acylphospholipids, but "neutral plasmalogens" (alkenyldiacylglycerols) and "diplasmalogens" (dialkenylphospholipids) also exist.[1] The prototypical plasmalogen is platelet-activating factor.[7]
^ abcdeChristie W. "Ether lipids - glyceryl ethers, plasmalogens, aldehydes, structure, biochemistry, composition and analysis". www.lipidmaps.org.
^Dean JM, Lodhi IJ (February 2018). "Structural and functional roles of ether lipids". Protein & Cell. 9 (2): 196–206. doi:10.1007/s13238-017-0423-5. PMC 5818364. PMID 28523433.
^Ford DA, Gross RW (July 1990). "Differential metabolism of diradyl glycerol molecular subclasses and molecular species by rabbit brain diglyceride kinase". The Journal of Biological Chemistry. 265 (21): 12280–6. doi:10.1016/S0021-9258(19)38342-5. PMID 2165056. S2CID 1042240.
^Dean, JM; Lodhi, IJ (February 2018). "Structural and functional roles of ether lipids". Protein & Cell. 9 (2): 196–206. doi:10.1007/s13238-017-0423-5. PMC 5818364. PMID 28523433.
^ abVillanueva, Laura; von Meijenfeldt, F. A. Bastiaan; Westbye, Alexander B.; Yadav, Subhash; Hopmans, Ellen C.; Dutilh, Bas E.; Damsté, Jaap S. Sinninghe (January 2021). "Bridging the membrane lipid divide: bacteria of the FCB group superphylum have the potential to synthesize archaeal ether lipids". The ISME Journal. 15 (1): 168–182. Bibcode:2021ISMEJ..15..168V. doi:10.1038/s41396-020-00772-2. PMC 7852524. PMID 32929208.
^"Di- and Tetra-Alkyl Ether Lipids of the Archaea". lipidmaps.org.
^Watson RR, De Meester F, eds. (2014). Omega 3 fatty acids in brain and neurological health. Elsevier Academic Press. doi:10.1016/C2012-0-06006-1. ISBN 978-0-12-410527-0.
biochemistry, an etherlipid refers to any lipid in which the lipid "tail" group is attached to the glycerol backbone via an ether bond at any position...
In organic chemistry, ethers are a class of compounds that contain an ether group—an oxygen atom connected to two organyl groups (e.g., alkyl or aryl)...
a diether. The 2,3-sn-glycerol structure and ether bond linkage are two key differences between lipids found in archaea vs those of bacteria and eukarya...
The lipid attached to the vinyl ether at sn-1 can be C16:0, C18:0, or C18:1 (saturated and monounsaturated), and the lipid attached to the acyl group at...
that is the hallmark of circulation-related diseases such as diabetes. Etherlipid oxidase (alkylglycerol monooxygenase, AGMO) catalyses the conversion...
PMID 17954212. Paltauf F (December 1994). "Etherlipids in biomembranes". Chemistry and Physics of Lipids. 74 (2): 101–139. doi:10.1016/0009-3084(94)90054-X...
aspects of archaeal biochemistry are unique, such as their reliance on etherlipids in their cell membranes, including archaeols. Archaea use more diverse...
GDGTs originate as archaeal membrane lipids, whose fatty acids are converted to glycerol via esterification (etherlipid). They were first recognized as being...
Armarego, Wilfred L. F. (1998). "Glyceryl-Ether Monooxygenase [EC 1.14.16.5]. A Microsomal Enzyme of EtherLipid Metabolism". Medicinal Research Reviews...
refrigeration compressors Thioester Transesterification Etherlipid, an ester that is a lipid and an ether Acylal ((R1−C(=O)−O−)(R2−C(=O)−O−)CH−R3) Ortho ester...
The lipid bilayer (or phospholipid bilayer) is a thin polar membrane made of two layers of lipid molecules. These membranes are flat sheets that form a...
Armarego, Wilfred L. F. (1998). "Glyceryl-Ether Monooxygenase [EC 1.14.16.5]. A Microsomal Enzyme of EtherLipid Metabolism". Medicinal Research Reviews...
include glycolysis, purine salvage, beta oxidation of fatty acids, and etherlipid synthesis. The main function that the glycosome serves is of the glycolytic...
Lipid droplets, also referred to as lipid bodies, oil bodies or adiposomes, are lipid-rich cellular organelles that regulate the storage and hydrolysis...
Armarego, Wilfred L. F. (1998). "Glyceryl-Ether Monooxygenase [EC 1.14.16.5]. A Microsomal Enzyme of EtherLipid Metabolism". Medicinal Research Reviews...
dehydrogenase with NAD+/NADH as cofactor. DHAP also has a role in the ether-lipid biosynthesis process in the protozoan parasite Leishmania mexicana. DHAP...
alkylglycerols, a specific subclass of etherlipids. This enzyme was first described in 1964 as a pteridine-dependent etherlipid cleaving enzyme. In 2010 finally...
Armarego, Wilfred L. F. (1998). "Glyceryl-Ether Monooxygenase [EC 1.14.16.5]. A Microsomal Enzyme of EtherLipid Metabolism". Medicinal Research Reviews...
ester linkages in bacteria/eukaryotes and by ether linkages in archaea. In bacteria and procaryotes, the lipids consist of diesters commonly of C16 or C18...
enzyme is also called lysophospholipase D. This enzyme participates in etherlipid metabolism. As of late 2007, only one structure has been solved for this...
therefore considered to be the prototype of synthetic anti-cancer lipids. "The antitumor etherlipid Edelfosine (ET-18-O-CH3) induces apoptosis in H-ras transformed...
Divinyl ether is the organic compound with the formula O(CH=CH2)2. It is a colorless, volatile liquid that has mainly been of interest as an inhalation...
enzyme is also called lysoplasmalogenase. This enzyme participates in etherlipid metabolism. Arthur G, Page L, Mock T, Choy PC (1986). "The catabolism...
Saghatelian A, Cravatt BF (October 2006). "An enzyme that regulates etherlipid signaling pathways in cancer annotated by multidimensional profiling"...
peptidoglycan by glycoproteins and lipoproteins. [L] Reverse DNA gyrase and etherlipid isoprenoids. [M] Phagocytosis. Cavalier-Smith T (2006). "Cell evolution...
Niessen S, Saghatelian A, Cravatt BF (Oct 2006). "An enzyme that regulates etherlipid signaling pathways in cancer annotated by multidimensional profiling"...
interact with the endoplasmic reticulum and cooperate in the synthesis of etherlipids (plasmalogens), which are important for nerve cells (see above). In filamentous...
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