Immunochemical Studies of Phospholipids. II. Syntheses of Cardiolipin and Its Analogues

Abstract

Bis(dipalmitoyl D, L -[alpha]-glyc erylphosphor yl) -1,3-glycerol disodium salt (I) was synthesized by the condensation of the silver salt of dipalmitoyl D,L-glycerophosphoric acid benzyl ester (XI) with 1,3-diiodopropanol benzyl ether, followed by debenzylation with sodium iodide and hydrogenolysis with palladium black. Bis(di-palmitoyl D,L-[alpha]-glycerylphosphoryl)-l,5-pentanediol disodium salt (HI), bis(dipalmitoyl D,L-[alpha]-glycerylphosphoryl)-l,4-butanediol disodium salt (IV), bis(dipalmitoyl D,L-[alpha]-glycerylphosphoryl)-l,2-ethanediol disodium salt (VI) and bis(dipalmitoyl D,L-[alpha]-glyceryl-phosphoryl)methanediol disodium salt (VII) were synthesized similarly by the condensation of the silver salt (XI) with alkyl diiodide or dibro- mide, followed by debenzylation with sodium iodide. Bis(benzylphos-phoryl)-l,3-propanediol disodium (X) was synthesized by condensation of silver dibenzyl phosphate with alkyl diiodide, followed by debenzylation with sodium iodide.