The preparation and characterization of the methoxy derivatives of polyunsaturated fatty acids: Stabilized product analogs of lipoxygenase catalysis |
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Authors: | Max O Funk Bruce Levison Maggie B Keller |
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Affiliation: | (1) Bowman-Oddy Laboratories, Department of Chemistry, University of Toledo, 43606 Toledo, OH |
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Abstract: | The products from the action of soybean lipoxygenase on a series of polyunsaturated fatty acids have been converted in 2 steps
into the corresponding methoxy derivatives. The product hydroperoxides were reduced in situ to alcohols with sodium borohydride.
The ethers were generated by treatment of the alcohols with sodium hydride and methyl iodide in tetrahydrofuran. 13-Methoxy-9(Z),11(E)-octadecadienoic,
15-methoxy-11(Z),13(E)-eicosadienoic and 15-methoxy-5(Z),8(Z),11(Z), 13(E)-eicosatetraenoic acids were thus prepared. The
methyl ethers were analyzed and the structures established by high performance liquid chromatography, nuclear magnetic resonance
and infrared spectrometry, polarimetry and mass spectroscopy (as methyl esters). The methylation reaction proceeds without
molecular rearrangements or racemiziation. |
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