A soluble enzyme preparation from a pseudomonad was shown to catalyze the conversion of linoleic acid to 10d-hydroxy-cis-Δ12-octadecenoic acid. The assignment of structure was based upon chromatographic studies, infrared spectroscopy, optical rotation studies, and, to a major extent, mass spectrometry, including combined gas-liquid chromatography-mass spectrometry, high resolution mass spectrometry, and the preparation of deuterium-labeled derivatives prior to mass spectrometry.
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Schroepfer et al. (1970) studied this question.
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