Stereochemical nature of the products of linoleic acid oxidation catalyzed by lipoxygenases from potato and soybean

Biochemical and Biophysical Research Communications
V NikolaevC C Reddy

Abstract

When linoleic acid was incubated with the purified potato lipoxygenase under O2 atmosphere, a mixture of 9 and 13-hydroperoxyoctadecadienoic acids was formed. Stereochemical analysis of the respective methyl-hydroxyoctadecadienoic acids revealed that the 9-isomer was in S-configuration whereas 13-hydroxyoctadecadienoic acid was a mixture of S (39%) and R (61%). Exactly the opposite was the case with the soybean lipoxygenase products, where the 13-isomer was found to be in S-configuration and 9-hydroxyoctadecadienoic acid - a mixture of S (73%) and R (27%). A general scheme is proposed for the stereochemical nature of oxidation products of enzymes which are predominantly either [+2] or [-2] lipoxygenases.

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Citations

Jan 31, 2008·Journal of Computer-aided Molecular Design·P AparoyP Reddanna
Jul 30, 1991·Biochimica Et Biophysica Acta·H W Gardner
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Aug 13, 2013·ChemSusChem·Konrad B OtteBernhard Hauer

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