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Synthesis and properties of phosphatidyl carnitine and phosphatidyl β‐methylcholine

1975; Wiley; Volume: 10; Issue: 1 Linguagem: Inglês

10.1007/bf02532189

1558-9307

Ulrich Hintze, G. Gercken,

Lipid Membrane Structure and Behavior

Abstract rac‐Phosphatidyl carnitine and racphosphatidyl β‐methylcholine were synthesized by direct condensation of phosphatidic acid and the appropriate alcohols in the presence of 2,4,6‐triisopropylbenzenesulphonylchloride and pyridine. Tetraphenylborates of the quarternary ammonium compounds β‐methylcholine and carnitine benzyl ester were shown to be particularly convenient for synthesis in homogeneous phase. Physical and chemical properties of the two phosphoglycerolipids and some intermediates were described. Phosphatidyl carnitine and phosphatidyl β‐methylcholine were hydrolyzed by phospholipase A 2 (phosphatide acyl‐hydrolase, EC 3.1.1.4), pancreatic lipase (triacylglycerol acyl‐hydrolase, EC 3.1.1.3), and phospholipase C from Bacillus cereus (phosphatidylcholine cholinephosphohydrolase, EC 3.1.4.3). Neither hydrolysis nor transphosphatidylation of phosphatidyl carnitine and phosphatidyl β‐methylcholine was achieved by phospholipase D (phosphatidylcholine phosphatidohydrolase, EC 3.1.4.4). The occurrence of phosphatidyl carnitine in embryonic chicken tissue was suggested by comparison with the synthesized compound. Phosphatidyl carnitine could not be detected in the tissue of rat embryos.