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Stereospecific Conversion of Oleic Acid to 10-Hydroxystearic Acid

From the ¹ From the Division of Biochemistry, Department of Chemistry and Chemical Engineering, University of Illinois, Urbana, Illinois 61801

The conversion of oleic acid to 10-d-hydroxystearic acid by a pseudomonad was studied in a medium enriched in deuterium oxide. The reaction occurred with stereospecific incorporation of 1 atom of solvent hydrogen at carbon atom 9. The location of the deuterium was established by a combination of chemical and mass spectrometric evidence. The hydroxyl function of the deuterium-labeled hydroxystearate was replaced by hydrogen through a series of standard organic reactions which should not affect the stereochemistry at carbon atom 9. The resulting deuterium-labeled stearate was incubated with a growing culture of a strain of Corynebacterium diphtheriae, a system which stereospecifically removes hydrogen in the d configuration at carbon atom 9 of stearate in the enzymatic introduction of the ⁹-double bond of oleic acid. Retention of the labeled hydrogen in the oleate was observed, indicating that the configuration of the deuterium in the stearate, and hence in the 10-hydroxystearate, was l.

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