Generation, total syntheses, and identification of biologically active oxidized ethanolamine phospholipids

ORGN 552

Bogdan G. Gugiu1, Mingjiang Sun1, and Robert G Salomon2. (1) Department of Chemistry, Case Western Reserve University, Cleveland, OH 44106, (2) Chemistry, Case Western Reserve University, Cleveland, OH 44106

Oxidation of three major ethanolamine phospholipids – docosahexaenoyl- (1), arachidonoyl- (2) and linoleyl-phosphatidylethanolamine (3) – generates truncated lipids 4a-c, 5a-c, 6a-c.  Unambiguous total syntheses of these oxidized lipids from lyso-phosphatidylethanolamine (7) confirmed their identities, allowed testing of their biological activities and LC-ES/MS determinations of their yields in the complex oxidation product mixtures.

 

Bioorganic, Molecular Recognition, Asymmetric Reactions and Syntheses
11:00 AM-1:00 PM, Wednesday, September 10, 2003 Javits Convention Center -- Hall 1B/1C, Poster

Division of Organic Chemistry
The 226th ACS National Meeting, New York, NY, September 7-11, 2003