title: Synthesis and properties of monofluorinated dimyristoylphosphatidylcholine derivatives: potential fluorinated probes for the study of membrane topology.
abstract: The synthesis of three monofluorinated dimyristoylphosphatidylcholine derivatives (F-DMPC), with the fluorine atom located on the acyl chain in position 2 of the glycerol (sn-2) is described. The synthetic strategy relies on the coupling of 1-myristoyl-2-hydroxy-sn-glycero-3-phosphocholine (lyso-PC) and three different fluorinated fatty acids. The latter were obtained from two different and complementary synthetic routes. Preliminary FTIR studies suggest that the presence of the fluorine atom does not significantly perturb the lipid conformational order and phase transition temperature and that these monofluorinated PC derivatives could be used as probes for the study of membrane topology, i.e. the location of drugs, peptides or proteins in membranes.
authors.affiliation: Department of Chemistry, PROTEO, CERMA, 1045 avenue de la Médecine, Université Laval, Québec, Canada. michele.auger@chm.ulaval.ca.
authors.forename: Jonathan
authors.initials: J
authors.lastname: Guimond-Tremblay
authors.forename: Marie-Claude
authors.initials: MC
authors.lastname: Gagnon
authors.forename: Jozy-Ann
authors.initials: JA
authors.lastname: Pineault-Maltais
authors.forename: Vanessa
authors.initials: V
authors.lastname: Turcotte
authors.forename: Michèle
authors.initials: M
authors.lastname: Auger
authors.forename: Jean-François
authors.initials: JF
authors.lastname: Paquin
mesh_terms: D004134:Dimyristoylphosphatidylcholine / Q000031:analogs & derivatives* / Q000138:chemical synthesis* / Q000737:chemistry; D005456:Fluorescent Dyes / Q000138:chemical synthesis / Q000737:chemistry*; D008051:Lipid Bilayers / Q000737:chemistry*; D015394:Molecular Structure; D017550:Spectroscopy, Fourier Transform Infrared; D013237:Stereoisomerism
chemical_list: D005456:Fluorescent Dyes; D008051:Lipid Bilayers; D004134:Dimyristoylphosphatidylcholine