Polyunsaturated fatty acids ( PUFAs) are one of the major constituent of lipids inside the cell membrane. Linoleic acid(LA), one of the most prevalent forms of PUFAs, possess 1,4-diene functional group. This functional group makes LA prone to oxidation through enzymatic or nonenzymatic reactions and conversion to 13or 9-hydroperoxy(HpODE). Following, HpODE rearrangement or fragmentation leads to variety of lipid metabolites forms. Among these scaffolds of linoleic acid metabolites,epoxyketooctadecenoicacid (EKODE)s specifically caught our attention. This family of metabolites is proven to exist in vivoinvolved in pathological states such as hypertension and obesity.Interesting physiological activities of EKODEs made us think about providing robust synthesis for each specific core (scaffold). Here in, we illustrate methodology towards total synthesis of EKODE. Likewise, comparative kinetics studies on reactivity of EKODEs along with HNE and ONE (known end metabolites of lipid peroxidation) will shed light on distinctive cabonylation characteristics of these metabolites. The outcomes are expected to provide detailed information towards human diseases that are associated with elevated levels of EKODEs.

Epoxyketooctadecenoicacid (EKODE)s synthesis via bifunctional conjunctive ylide and their comparative kinetic studies towards model nucleophile

247th National Meeting (2014)

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