Stereochemistry of the epoxidation of fatty acids catalyzed by soybean peroxygenase.
The stereochemistry of C18 unsaturated fatty acids epoxidation catalyzed by detergent-solubilized and partially purified soybean peroxygenase was determined by chiral phase HPLC. Linoleic acid was oxidized into 9, 10- and 12,13-cis-epoxyoctadecenoic acids with a high enantiofacial selectivity. A 5.2:1 and 2.3:1 ratio respectively in favor of the 9(R), 10(S)- and 12(R), 13(S)-epoxy enantiomers was observed. These epoxy-derivatives of linoleic acid have the chirality of metabolites known to be involved in plant defense against fungi. This finding is of importance in establishing a physiological role for the peroxygenase.
Blee
E
E
Institut de Biologie Moléculaire des Plantes (CNRS UPR-406), DECM, Institut de Botanique, Strasbourg, France.
Schuber
F
F
D002851:Chromatography, High Pressure Liquid; D003902:Detergents; D004852:Epoxy Compounds / Q000378:metabolism*; D005227:Fatty Acids / Q000378:metabolism*; D006864:Hydrogenase / Q000378:metabolism*; D008041:Linoleic Acids / Q000378:metabolism; D008861:Microsomes / Q000201:enzymology; D013025:Glycine max / Q000201:enzymology*; D013237:Stereoisomerism
D003902:Detergents; D004852:Epoxy Compounds; D005227:Fatty Acids; D008041:Linoleic Acids; D006864:Hydrogenase