Synthesis and characterization of deoxy analogues of diphytanylglycerol phospholipids.
Novel analogues of diphytanyl phospholipids, 2,3-diphytanyl sn-1-glycerol-1-phosphoryl-1'-(1',3'-propanediol) (dPG), 2,3-diphytanyl-sn-glycerol-1-phosphoryl-1'-propanol (ddPG) and 2,3-diphytanyl-sn-glycerol-1-phosphoryl-1'-(1',3'-propanediol-3'-p hosphate) (dPGP), were synthesized according to modifications of previously published procedures. The samples were TLC and analytically pure and were characterized by 13C- and 1H-NMR and negative FAB/MS. The pK values of dPGP in aqueous dispersions or in methanol/water (1:1, v/v) were determined by potentiometric titration and compared with those of 2,3-diphytanyl-sn-glycerol-1-phosphoryl-3'-sn-glycerol-1'-phosphat e (PGP). The dissociation constant of the third ionizable POH group of dPGP was more than 2 pK units higher than that of PGP, indicating that the free glycerol hydroxyl group plays an important role in headgroup conformation and stabilization, perhaps through hydrogen bonding with the phosphate group(s).
Stewart
L C
LC
Department of Biochemistry, University of Ottawa, Canada.
Kates
M
M
Smith
I C
IC
D055598:Chemical Phenomena; D002621:Chemistry; D002855:Chromatography, Thin Layer; D009682:Magnetic Resonance Spectroscopy; D011409:Propylene Glycols / Q000032:analysis / Q000138:chemical synthesis*
D011409:Propylene Glycols; C059130:1-bis(trichloroethyl)phosphoryl-1,3-propanediol; C059129:1-O-benzoyl-1,3-propanediol