SYNTHESIS OF -PALMITOYL-2-HEXADECYL-SN-GLYCERO-3-PHOSPHOCHOLINE (PHPC)

A general method for the chirospecific synthesis of 1-acyl-2-alkyl-sn- glycero-3-phosphocholines is described. -Palmitoyl-2-hexadecyl-sn-glyc ero-3-phosphocholine (PHPC) was synthesized in 18% overall yield in te n steps via five new synthetic intermediates, and 1-acetyl-2-hexadecyl -sn-glycero-3-phosphocholine (AHPC) was also synthesized. 1-Acyl-2-alk yl-sn-glycero-3-phosphocholine which have not been found to exist in n ature, are ether lipid analogs of 1,2-diacyl-sn-glycero-3-phosphocholi nes, which are important components of cell membranes. Biophysical stu dies of hydrated bilayers of PHPC will be of interest in probing the c ritical importance of the central region of these amphiphilic molecule s to the molecular assemblies that are formed.