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Issue 28, 2014
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Evaluation of the effect of fluorination on the property of monofluorinated dimyristoylphosphatidylcholines

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Abstract

The synthesis of three monofluorinated dimyristoylphosphatidylcholines (F-DMPC's), with the fluorine atom located at the extremities of 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 (14:0 lyso-PC) and three different fluorinated fatty acids. FTIR results suggest that the presence of the fluorine atom does not significantly perturb the lipid phase transition temperature and conformational order even though a small increase in the phase transition temperature is observed for the 14F derivative. Overall, comparison with previously reported F-DMPC's where the fluorine atom is located in the middle or close from either side supports the fact that monofluorination of the acyl chain in sn-2 brings minimal perturbation to the lipid bilayer. F-DMPC's could therefore potentially be used as NMR probes for the investigation at the molecular level of the interaction between drugs or peptides and lipid membranes and for the study of membrane topology.

Graphical abstract: Evaluation of the effect of fluorination on the property of monofluorinated dimyristoylphosphatidylcholines

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Publication details

The article was received on 06 May 2014, accepted on 25 May 2014 and first published on 27 May 2014


Article type: Paper
DOI: 10.1039/C4OB00934G
Citation: Org. Biomol. Chem., 2014,12, 5126-5135
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    Evaluation of the effect of fluorination on the property of monofluorinated dimyristoylphosphatidylcholines

    M. Gagnon, B. Turgeon, J. Savoie, J. Parent, M. Auger and J. Paquin, Org. Biomol. Chem., 2014, 12, 5126
    DOI: 10.1039/C4OB00934G

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