Journal of Lipid Research, Vol 29, 1101-1104, Copyright © 1988 by Lipid Research, Inc.
Synthesis of a spin-labeled phospholipid for studying membrane dynamics in intact mammalian cells
J Joseph and CS Lai
National Biomedical ESR Center, Department of Radiology, Medical College of Wisconsin, Milwaukee 53226.
We report here the synthesis of a spin-labeled phospholipid, 1-
palmitoyl-2-(4-doxylpentanoyl)glycerophosphocholine. The synthetic route
for this probe involves two major steps: 1) the synthesis of 4-
doxylpentanoic acid from ethyl levulinate and 2-amino-2-methyl propanol,
and 2) the synthesis of the lipid from 4-doxylpentanoic acid and
lysolecithin. The efficiency and yield of both steps have been greatly
improved. This represents the first instance that the synthesis of this
important spin-labeled phospholipid is described in detail. Because it
mimics the native lipid molecule and can be readily incorporated into
biological membranes, this probe should be extremely useful for studying
lipid dynamics in the plasma membrane of intact mammalian cells using
electron spin resonance (ESR) spectroscopy.
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