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Biohydrogenation of Unsaturated Fatty Acids

VI. SOURCE OF HYDROGEN AND STEREOSPECIFICITY OF REDUCTION

From the ¹ From the Department of Biochemistry, North Carolina State University, Raleigh, North Carolina 27607

The biohydrogenation of either linoleic acid or cis-9, trans-11, cis-13-octadecatrienoic acid (punicic acid) by Butyrivibrio fibrisolvens results in the formation of trans-11-octadecenoic acid. Incubation of whole cells with tritiated formate, tritiated succinate, and glucose labeled with tritium in various positions failed to result in the labeling of the monoenoic acid product. In contrast, experiments performed in D₂O indicated that deuterium was incorporated at the cis double bond(s) reduced by the microorganism. This reduction, which takes place stereospecifically, was found to occur by cis addition to the d side of cis-9, trans-11-octadecadienoic acid, an intermediate in the biohydrogenation of linoleic acid. The distribution of deuterium at the reduced carbon atoms shows an isotope effect and leads to the speculation that reduction occurs by addition of a proton and hydride ion mediated by an unknown carrier.

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