title: Total synthesis of isoprostanes: discovery and quantitation in biological systems.
abstract: Isoprostanes (iP's), a new class of natural products isomeric with prostaglandins, are formed as the result of free radical oxygenation of polyunsaturated fatty acids. We have identified these iP's and developed analytical methodology to measure them in biological fluids. The approach we took, which led to the discovery and measurement of iP's, is as follows: (1) based on some biochemical and chemical considerations, we proposed possible structures for these isoprostanes; (2) we performed the total syntheses of some of these iP's, in particular Groups III through VI, and used them as markers for their discovery in biological fluids and developed a GC/MS and an LC/MS methodologies based on iPF2alpha-III, iPF2alpha-VI, and 8,12-iso-iPF2alpha-VI; (3) with the help of these assays, we measured elevated levels of iP's in Alzheimer's disease and atherosclerosis.
authors.affiliation: Department of Chemistry, Claude Pepper Institute, Florida Institute of Technology, 150 West University Blvd., Melbourne, FL 32901, USA. jrokach@fit.edu
authors.forename: Joshua
authors.initials: J
authors.lastname: Rokach
authors.forename: Seongjin
authors.initials: S
authors.lastname: Kim
authors.forename: Sophie
authors.initials: S
authors.lastname: Bellone
authors.forename: John A
authors.initials: JA
authors.lastname: Lawson
authors.forename: Domenico
authors.initials: D
authors.lastname: Praticò
authors.forename: William S
authors.initials: WS
authors.lastname: Powell
authors.forename: Garret A
authors.initials: GA
authors.lastname: FitzGerald
mesh_terms: D028421:Isoprostanes / Q000032:analysis / Q000138:chemical synthesis*; D009626:Terminology as Topic
chemical_list: D028421:Isoprostanes