Formation of 12-[18O]Oxo-cis-10,cis-15-phytodienoic acid from 13-[18O]hydroperoxylinolenic acid by hydroperoxide cyclase |
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| Authors: | Brady A. Vick Paul Feng Don C. Zimmerman |
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| Affiliation: | (1) U.S. Department of Agriculture, Science and Education Administration, Agricultural Research, Department of Biochemistry, North Dakota State University, 58105 Fargo, ND |
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| Abstract: | 13-[18O] Hydroperoxylinolenic acid was permitted to react with an extract of flaxseed acetone powder containing hydroperoxide cyclase activity. The resulting product, 12-oxo-cis-10,cis-15-phytodienoic acid (12-oxo-PDA), contained18O in the carbonyl oxygen at carbon 12, suggesting that an epoxide was an intermediate in the hyderoperoxide cyclase reaction. A substrate specificity study showed that acis double bond β,γ to the conjugated hydroperoxide group was essential for the substrate to be converted to a cyclic product by hydroperoxide cyclase. |
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