Synthesis of site-specifically labeled arachidonic acids as mechanistic probes for prostaglandin H synthase.
[structure: see text] Prostaglandin H synthase catalyzes the first committed step in the biosynthesis of prostaglandins and thromboxane. Herein we report the synthesis of four site-specifically labeled arachidonic acids for investigation of the radical intermediate formed during this enzymatic reaction. Two compounds were prepared using a common C9-C11 fragment, while another target was synthesized using a previously reported advanced intermediate. An alkyne coupling followed by hydrogenation and Wittig reaction was used to prepare the final labeled substrate.
Peng
Sheng
S
Roger Adams Laboratory, Department of Chemistry, University of Illinois, 600 S. Mathews Avenue, Urbana, Illinois 61801, USA.
McGinley
Chris M
CM
van der Donk
Wilfred A
WA
D001095:Arachidonic Acids / Q000032:analysis / Q000737:chemistry / Q000378:metabolism*; D006865:Hydrogenation; D015335:Molecular Probes / Q000032:analysis / Q000737:chemistry / Q000378:metabolism*; D015394:Molecular Structure; D011451:Prostaglandin-Endoperoxide Synthases / Q000378:metabolism*
D001095:Arachidonic Acids; D015335:Molecular Probes; D011451:Prostaglandin-Endoperoxide Synthases