Condensation of monophenylphosphoryl N-carbobenzyloxy DL-serine benzyl ester monosilver salt with the appropriate a-iodo diglyceride by the procedure of Bevan, Malkin, and Tiplady for the synthesis of racemic a-(distearoy1)-phosphatidyl serine, d o r d e d dihexanoyl-, dioctanoyl-, and didecanoyl-DL-a-glycerylphenylphosphoryl N-carbobenzyloxy DL-serine benzyl esters. These esters, upon removal of the protective phenyl, benzyl, and carbobenzyloxy groups by catalytic hydrogenolysis, gave the short-chain fatty acid, DL-a-phosphatidyl DL-serines. In contrast to a-(distearoyl) phosphatidyl serine, these three phosphatidyl serines easily form an emulsion with water and should prove to be suitable substrates for biological and chemical studies.
YNTHETIC PROCEDURES are available for the S preparation of phosphatidyl serine containing a long-chain fatty acid (1, 2). However, in- vestigation of the biological properties and effects of this compound is hampered by its insolubility in water and by the difficulty with which i t forms aqueous emulsions (3). The work presented here describes the synthesis of phosphatidyl serines containing short-chain fatty acids. Such serines can be easily emulsified; therefore, they may be of value i n biological investigations.