Glycerophospholipid synthesis: improved general method and new analogs containing photoactivable groups

Abstract

Current methods for phospholipid synthesis involving acylation of sn-glycero-3-phosphorylcholine, lysolecithins, and related glycerophosphate esters are not satisfactory. With N,N-dimethyl-4-aminopyridine as a catalyst and moderate amounts of fatty acid anhydrides (1.2-1.5 mol equiv per OH group), diacyl or 1,2-mixed diacylphosphatidylcholines, N-protected phosphatidylethanolamines, and phosphatide acids now can be conveniently prepared in high yields (75-90%). New phospholipids containing photoactivable groups, such as trifluorodiazopropionyl, diazirinophenoxy, 2-nitro-4-azidophenoxy, m-azidophenoxy, and alpha, beta-unsaturated keto groups, in the fatty acyl chains have been prepared. These phospholipids are of interest in studies of lipid-lipid and lipid-protein interactions in biological membranes.