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. 2006 Jan 25;128(3):720-1.
doi: 10.1021/ja056517y.

Convergent oxygenation of arachidonic acid by 5-lipoxygenase and cyclooxygenase-2

Claus Schneider  1 , William E Boeglin, Huiyong Yin, Donald F Stec, Markus Voehler
Affiliations

Convergent oxygenation of arachidonic acid by 5-lipoxygenase and cyclooxygenase-2

Claus Schneider et al. J Am Chem Soc. .

Abstract

5-Lipoxygenase and cyclooxygenase-2 (COX-2) initiate the biosynthesis of distinct families of mediators from arachidonic acid (leukotrienes and prostaglandins, respectively) and are each the target of anti-inflammatory medications. Here we show that the product of 5-lipoxygenase, 5S-hydroxyeicosatetraenoic acid, is selectively and efficiently triply oxygenated by COX-2, implicating a cross-pathway interaction. The product is a unique diendoperoxide, potentially representing the parent compound of a novel group of lipid mediators.

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Figures

Figure 1
Figure 1
Reaction of COX-2 with 5S-HETE. (A) Oxygen electrode assays using arachidonic acid (left panel), 5S-HETE (middle), and 5RHETE (right). Oxygen uptake was recorded upon addition of COX-2 (short arrow) and substrate (long arrow). (B) Reversed-phase HPLC analysis of the reaction products of [14C]5S-HETE with COX-2. (C) 1H
Scheme 1
Scheme 1
Proposed mechanism of formation of 1 by COX-2.
See this image and copyright information in PMC

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