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Biophys J, October 1998, p. 1858-1868, Vol. 75, No. 4

A New Monofluorinated Phosphatidylcholine Forms Interdigitated Bilayers

Donald J. Hirsh,* Nancy Lazaro,# Lee R. Wright,# Joan M. Boggs,§ Thomas J. McIntosh, Jacob Schaefer,* and Jack Blazyk#

 *Department of Chemistry, Washington University, St. Louis, Missouri 63130 USA;  #Department of Biomedical Sciences, College of Osteopathic Medicine, and Department of Chemistry and Biochemistry, College of Arts and Sciences, Ohio University, Athens, Ohio 45701 USA;  §Department of Biochemistry, Research Institute, Hospital for Sick Children, and Department of Laboratory Medicine and Pathobiology, University of Toronto, Toronto, Ontario M5G 1X8, Canada; and  Department of Cell Biology, Duke University Medical Center, Durham, North Carolina 27710 USA

16-Fluoropalmitic acid was synthesized from 16-hydroxypalmitic acid using diethylaminosulfur trifluoride. This monofluorinated fatty acid then was used to make 1-palmitoyl-2-[16-fluoropalmitoyl]-phosphatidylcholine (F-DPPC) as a fluorinated analog of dipalmitoylphosphatidylcholine (DPPC). Surprisingly, we found that the phase transition temperature (Tm) of F-DPPC occurs near 50°C, ~10°C higher than its nonfluorinated counterpart, DPPC, as judged by both differential scanning calorimetry and infrared spectroscopy. The pretransition observed for DPPC is absent in F-DPPC. A combination of REDOR, rotational-echo double-resonance, and conventional solid-state NMR experiments demonstrates that F-DPPC forms a fully interdigitated bilayer in the gel phase. Electron paramagnetic resonance experiments show that below Tm, the hydrocarbon chains of F-DPPC are more motionally restricted than those of DPPC. X-ray scattering experiments confirm that the thickness and packing of gel phase F-DPPC is similar to that of heptanetriol-induced interdigitated DPPC. F-DPPC is the first phosphoglyceride containing sn-1 and sn-2 ester-linked fatty acyl chains of equal length that spontaneously forms interdigitated bilayers in the gel state in the absence of inducing agents such as alcohols.

Biophys J, October 1998, p. 1858-1868, Vol. 75, No. 4
© 1998 by the Biophysical Society   0006-3495/98/10/1858/11  $2.00


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