Syntheses of 2H- and 13C-labeled 1,2-di- O-hexadecyl- sn-glycero-3-phosphoethanolamines and 1,2-di- O-hexadecyl- sn-glycero-3-phosphocholines

• Published in: Chemistry and physics of lipids Vol. 50; no. 2; pp. 163 - 169
• Main Authors: Abdelmageed, Osama H., Duclos, Richard I., Griffin, Robert G., Siminovitch, David J., Ruocco, Martin J., Makriyannis, Alexandros
• Format: Journal Article
• Language: English
• Published: Shannon Elsevier Ireland Ltd 01.05.1989; Elsevier Science
• Subjects: 13C-labeled ether lipid; 2H-labeled ether lipid; Chemistry; ether lipid; Exact sciences and technology; Lipids; Organic chemistry; phospholipid; Preparations and properties; sn-glycero-3-phosphocholine; sn-glycero-3-phosphoethanolamine; 2H-labeled ether lipid; sn-glycero-3-phosphoethanolamine; sn-glycero-3-phosphocholine; phospholipid; 13C-labeled ether lipid; ether lipid; Phospholipid; Complex lipid
• ISSN: 0009-3084; 1873-2941
• DOI: 10.1016/0009-3084(89)90040-6

Improved syntheses of 1,2-di- O-hexadecyl- sn-glycero-3-phosphoethanolamine and 1,2-di- O-hexadecyl- sn-glycero-3-phosphocholine were performed in 71% and 57% overall yields, respectively. Reported reactions which have been greatly improved include the dialkylation of 3- O-benzyl- sn-glycerol, the hydrogenolysis of the 3- O-benzyl- sn-glycerol derivative, and the quaternization of the sn-glycero-3-phosphoethanolamine to the corresponding sn-glycero-3-phosphocholine. Several 2H-, and 13C-labeled analogs of 1,2- di- O-hexadecyl- sn-glycero-3-phosphocholine were then prepared by the appropriate modifications of our synthetic sequence.