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A more recent version of this article appeared on April 1, 2006

Papers In Press, published online ahead of print January 3, 2006
J. Lipid Res., doi:10.1194/jlr.D500042-JLR200
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Submitted on December 14, 2005
Revised on January 3, 2006
Accepted on January 3, 2006

A simplified enzymatic method of 10,17-dihydro(pero)xydocosahexa-4Z,7Z,11E,13Z,15E,19Z-enoic acid synthesis by soybean lipoxygenase

Igor A. Butovich

Ophthalmology Dept., University of Texas Southwestern Medical Center, Dallas, TX 75390-9057

Corresponding Author: igor.butovich{at}utsouthwestern.edu

A product of lipoxygenase (LOX) oxidation of docosahexaenoic acid (DHA), 10,17-dihydro(pero)xydocosahexa-4Z,7Z,11E,13Z,15E,19Z-enoic acid [10,17(S)-diH(P)DHA], was obtained through various reaction pathways that involved DHA, 17(S)-hydro(pero)xyDHA [17(S)-H(P)DHA], soybean LOX (sLOX) and potato tuber LOX (ptLOX) in various combinations. The structure of the product was confirmed by HPLC, UV-spectrometry, GC-MS, MS/MS and NMR-spectroscopy. It has been found that 10,17-diH(P)DHA formed by sLOX through direct oxidation of either DHA or 17(S)-H(P)DHA was apparently identical to the product of ptLOX oxidation of the latter. The sLOX- and ptLOX-derived samples of 10,17-diHDHAs coeluted under the conditions of normal, reverse, and chiral phase HPLC analyses, displayed identical UV absorption spectra with maxima at 260, 270 and 280 nm, and had similar one-dimensional and two-dimensional proton NMR spectra. Analysis of their NMR spectra led to a conclusion that 10,17-diHDHA formed by sLOX had solely 11E,13Z,15E-configuration of the conjugated triene fragment, which was identical to the previously published structure of its ptLOX derived counterpart [Butovich, Hamberg, and Rådmark, Lipids, 2005 and Butovich, J. Lipid Res., 2005]. Based on the cis,trans geometry of the reaction products, a conclusion is made that in the tested conditions sLOX catalyzed direct double dioxygenation of DHA. Compared to the previously described two-enzyme method that involved sLOX and ptLOX, the current simplified one-enzyme procedure utilizes only sLOX as catalyst of both the dioxygenation steps.


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