Synthesis of 1-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. 1-Palmitoyl-2-hexadecyl-sn-glycero-3-phosphocholine (PHPC) was synthesized in 18% overall yield in ten steps via five new synthetic intermediates, and 1-acetyl-2-hexadecyl-sn-glycero-3- phosphocholine (AHPC) was also synthesized. 1-Acyl-2-alkyl-sn-glycero-3-phosphocholines, which have not been found to exist in nature, are ether lipid analogs of 1,2-diacyl-sn-glycero-3-phosphocholines, which are important components of cell membranes. Biophysical studies of hydrated bilayers of PHPC will be of interest in probing the critical importance of the central region of these amphiphilic molecules to the molecular assemblies that are formed.
Duclos
R I
RI
Biophysics Department, Housman Medical Research Center, Boston University School of Medicine, MA 02118-2394.
D008051:Lipid Bilayers / Q000138:chemical synthesis*; D010742:Phospholipid Ethers / Q000138:chemical synthesis*; D013237:Stereoisomerism
D008051:Lipid Bilayers; D010742:Phospholipid Ethers; C028144:palmitoyl-palmityl-lecithin ether; C082824:1-hexadecyl-2-palmitoyl-sn-glycero-3-phosphocholine