The total synthesis of phosphatidyl(Dioleoyl)hydroxy-l-proline and its activity in blood-clotting systems.

The phthalimidomethyl ester ofN-anisyloxycarbonyl-hydroxy-L: -proline was combined with phosphorus oxychloride andrac-1,2-diolein. The diolein was made by large-scale preparative application of the method of Krabisch and Borgström (1). The protected phosphatide, obtained by the phosphorylation reaction, was stripped of its protective groups under mild conditions. The phosphatidyl(dioleoyl)-hydroxy-L: -proline was purified by TEAE cellulose (acetate) chromatography, as developed by Rouser (6), also by silicic acid chromatography. Aqueous dispersions of the material were tested for anticoagulant activity in the antithrom-boplastin test and the Hicks-Pitney test. The new phosphatide had about one-tenth of the activity of beef brain phosphatidylserine.