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. 2021 Feb 11;9:617984. doi: 10.3389/fcell.2021.617984

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Copyright © 2021 Angelova, Angelov, Drechsler, Bizien, Gorshkova and Deng.

This is an open-access article distributed under the terms of the Creative Commons Attribution License (CC BY). The use, distribution or reproduction in other forums is permitted, provided the original author(s) and the copyright owner(s) are credited and that the original publication in this journal is cited, in accordance with accepted academic practice. No use, distribution or reproduction is permitted which does not comply with these terms.

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Chemical structures of custom-produced polyunsaturated fatty acid (PUFA)-ether or ester type glycerophospholipids with long tails comprised of docosapentaenoyl (DPA) chains. Plasmalogens (1-alkyl-1′-enyl,2-acyl ether phospholipids) are obtained with phosphocholine and phosphoethanolamine headgroups, namely, 1-O-1′-(Z)-hexadecenyl-2-(4Z,7Z,10Z,13Z,16Z-docosapentaenoyl)-sn-glycero-3-phosphocholine, C16:1p-22:5n6 PC (top), and 1-O-1′-(Z)-hexadecenyl-2-(4Z,7Z,10Z,13Z,16Z-docosapentaenoyl)-sn-glycero-3-phosphoethanolamine, C16:1p-22:5n6 PE (middle). As a diacyl ester lipid, 1,2-bis(4Z,7Z,10Z,13Z,16Z-docosapentaenoyl)-sn-glycero-3- phosphoinositol, 22:5n6 PI, is enriched in docosapentaenoyl (DPA) moieties in order to increase the hydrophobic lipid volume with regard to the bulky phosphoinositol (PI) polar headgroup. Monoolein (bottom) is a single-chain monoglyceride used as a colipid in the studied mixed nanoassemblies.