Synthesis and properties of monofluorinated dimyristoylphosphatidylcholine derivatives: potential fluorinated probes for the study of membrane topology

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)...

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Bibliographic Details
Published in:Organic & biomolecular chemistry 2012-02, Vol.10 (6), p.1145-1148
Main Authors: Guimond-Tremblay, Jonathan, Gagnon, Marie-Claude, Pineault-Maltais, Jozy-Ann, Turcotte, Vanessa, Auger, Michèle, Paquin, Jean-François
Format: Article
Language:English
Subjects:
Dimyristoylphosphatidylcholine - analogs & derivatives
Dimyristoylphosphatidylcholine - chemical synthesis
Dimyristoylphosphatidylcholine - chemistry
Fluorescent Dyes - chemical synthesis
Fluorescent Dyes - chemistry
Lipid Bilayers - chemistry
Molecular Structure
Spectroscopy, Fourier Transform Infrared
Stereoisomerism
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Summary: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.
ISSN:1477-0520
1477-0539
DOI:10.1039/c2ob06570c