Stereochemical nature of the products of linoleic acid oxidation catalyzed by lipoxygenases from potato and soybean.
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.
Nikolaev
V
V
Department of Veterinary Science, Pennsylvania State University, University Park 16802.
Reddanna
P
P
Whelan
J
J
Hildenbrandt
G
G
Reddy
C C
CC
D002851:Chromatography, High Pressure Liquid; D019787:Linoleic Acid; D008041:Linoleic Acids / Q000378:metabolism*; D008054:Lipid Peroxides; D008084:Lipoxygenase / Q000378:metabolism*; D011198:Solanum tuberosum / Q000201:enzymology*; D013025:Glycine max / Q000201:enzymology*; D013237:Stereoisomerism
D008041:Linoleic Acids; D008054:Lipid Peroxides; C038649:13-hydroperoxy-9,11-octadecadienoic acid; C049606:9-hydroperoxy-11,12-octadecadienoic acid; D019787:Linoleic Acid; D008084:Lipoxygenase