Synthesis of isotopically labeled arachidonic acids to probe the reaction mechanism of prostaglandin H synthase

…, G Wu, RJ Kulmacz, WA van der Donk

Index: Peng, Sheng; Okeley, Nicole M.; Tsai, Ah-Lim; Wu, Gang; Kulmacz, Richard J.; Van der Donk, Wilfred A. Journal of the American Chemical Society, 2002 , vol. 124, # 36 p. 10785 - 10796

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Citation Number: 38

Abstract

Prostaglandin H synthase (PGHS) catalyzes the conversion of arachidonic acid to prostaglandin G2 in the cyclooxygenase reaction. The first step of the mechanism has been proposed to involve abstraction of the pro-S hydrogen atom from C13 to generate a pentadienyl radical spanning C11-C15. We report here the synthesis of six site-specifically deuterated arachidonic acids to investigate the structure of the radical intermediate. The ...