Synthesis of 7-thiaarachidonic acid as a mechanistic probe of prostaglandin H synthase-2.
The mechanism by which prostaglandin synthase converts arachidonic acid to prostaglandin G(2), creating five new chiral centers in the process, is still incompletely understood. The first radical intermediate has been characterized by EPR spectroscopy but subsequent proposed intermediates have not succumbed to detection. We report the synthesis of 7-thiaarachidonic acid designed to stabilize one of the proposed radical intermediates, which may allow its detection.
McGinley
Chris M
CM
Roger Adams Laboratory, Department of Chemistry, University of Illinois, 600 S. Mathews Avenue, Urbana, IL 61801, USA.
Jacquot
Cyril
C
van der Donk
Wilfred A
WA
D001095:Arachidonic Acids / Q000138:chemical synthesis*; D051546:Cyclooxygenase 2 / Q000737:chemistry*; D004578:Electron Spin Resonance Spectroscopy; D015335:Molecular Probes
D001095:Arachidonic Acids; D015335:Molecular Probes; D051546:Cyclooxygenase 2