A general route to glycerophospholipids modified in the hydrophobic region (Friedel–Crafts reaction introducing arene modifiers into natural glycerophospholipids)

Abstract A useful method for incorporation of aromatic molecules into hydrophobic moiety of natural lipids was devised. A number of fluorescent labeled phospholipids (anthryl- and pyrenyl-labeled phosphatidylcholines, phosphatidylethanolamines, phosphatidylinositols and diphosphatidylglycerols) as well as phospholipids immobilized on aryl-containing carriers were prepared in one step by interaction of natural unsaturated glycerophospholipids with corresponding arenes under the conditions of Friedel–Crafts alkylation. Localization of the label in acyl moieties corresponding to distribution of unsaturated fatty acyl residues in natural glycerophospholipid molecules was established by methods of chemical and enzymatic degradation.