Tetrahedron

Synthesis of two analogues of arachidonic acid and their reactions with 12-lipoxygenase

M Labelle, JP Falgueyret, D Riendeau, J Rokach

Index: Labelle, Marc; Falgueyret, Jean-Pierre; Riendeau, Denis; Rokach, Joshua Tetrahedron, 1990 , vol. 46, # 18 p. 6301 - 6310

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Citation Number: 23

Abstract

Two analogues of arachidonic acid (AA) were synthesized and their reaction with purified porcine 12-lipoxygenase was investigated. The analogue (Z, Z, Z, E)-5, 8, 11, 13 eicosatetraienoic acid 1 was found to be a substrate for the enzyme, being oxidized at one third the rate of AA. The structure of the lipoxygenation product, as well as its absolute stereochemistry, were determined by comparison of the enzymatic reaction product with a ...