Towards the synthesis of 5,6-epoxy-E2-isoprostane

Under condition of oxidative stress, free radicals mediated peroxidation of polyunsaturated fatty acids, generating in vivo cyclic metabolites like isoprostanes, neuroprostanes and phytoprostanes in human and plants respectively. In 1999, was reported that phospholipids from minimally modified-low density lipoproteins (MM-LDL) containing arachidonic acid, were converted by ROS to 1-palmitoyl-2-(5, 6-epoxyisoprostane E2)-sn-glycero-3-phosphatidylcholine (PEIPC). PEIPC, activates human aortic endothelial cell to bind monocytes, so it plays a pivotal role in the early development of arteriosclerosis and other inflammatory conditions.of the free acid 5,6-epoxy-E2-isoprostane which derives from hydrolysis of phosphatidylcholine-bound of PEIPC , to provide an anti-inflammatory effect by reducing secretion of the pro-inflammatory cytokines, IL-6 and IL-12. In this report, we will discuss about the possibility to synthetize 5,6-epoxy-E2-isoprostane through a different and innovative synthetic pathway, using a stereo controlled system, that allows to achieve the skeleton core of the molecule starting from bicyclo (3.3.0) octane.Regarding the connection of the α-side chain to the core, we want to analyze a new strategy by using a ligand which needs to be synthetize and verify its functionality through methodological studies.Using this kind of molecule, should be possible to promote the coupling between the aldehyde function of the core and the epoxide function of the future α-chain.

Verso la sintesi del 5,6-epossi-E2-isoprostano