Synthesis and biological activity of nitrated lipids, novel hormone-like signaling molecules

ORGN 669

Steven R. Woodcock, swoodcoc@uoregon.edu, Adam Marwitz, and Bruce P. Branchaud, bbranch@uoregon.edu. Department of Chemistry, University of Oregon, Eugene, OR 97403-1253
Peroxynitrite, a reactive nitrogen species (RNS) produced by oxidative stress, is believed to react with unsaturated fatty acids to produce nitrated lipids in vivo. Nitrated lipids contain a highly reactive nitroalkene functional group. Recent studies have shown that nitrated lipids exhibit several biological activities including protein modification, nitric oxide formation and the regulation of protein activities. We describe efficient, scalable regiospecific and stereoselective syntheses of representative nitrated lipids. We also present data from resulting biochemical investigations of nitrated lipids.