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Synthesis and properties of phosphatidyl carnitine and phosphatidyl β‐methylcholine
Author(s) -
Hintze Ulrich,
Gercken Guenther
Publication year - 1975
Publication title -
lipids
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.601
H-Index - 120
eISSN - 1558-9307
pISSN - 0024-4201
DOI - 10.1007/bf02532189
Subject(s) - carnitine , chemistry , phosphatidylcholine , hydrolysis , biochemistry , phosphatidic acid , hydrolase , stereochemistry , enzyme , phospholipid , membrane
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.