A fatty acid alpha-ketol, a product of the plant lipoxygenase pathway, is oxidized to 3(Z)-dodecendioic acid by a bacterial monooxygenase.
The fatty acid alpha-ketol 13-hydroxy-12-oxo-9(Z)-octadecenoic acid (methyl ester) was incubated with a bacterial culture isolated from soil. The bacteria (tentatively identified as Ralstonia sp.) exhibited strong monooxygenase activity growing on 2-tridecanone as sole source of carbon. They catalyzed a Baeyer-Villiger type of oxidation and converted the alpha-ketol to 3(Z)-dodecendioic acid. 3(Z)-Dodecendioic acid was isolated from the incubation mixture and identified by comparison with an authentic reference compound. These findings offer both a physiological role for alpha-ketol fatty acids in plant lipid hydroperoxide metabolism and new insights into an alternative biosynthetic pathway leading to traumatic acid (2(E)-dodecendioic acid).
Schneider
C
C
Lehrstuhl für Lebensmittelchemie, Universität Würzburg, Germany.
Wein
M
M
Harmsen
D
D
Schreier
P
P
D001426:Bacterial Proteins / Q000502:physiology*; D006088:Gram-Negative Aerobic Bacteria / Q000201:enzymology* / Q000254:growth & development; D019746:Intramolecular Oxidoreductases; D007535:Isomerases / Q000378:metabolism; D019787:Linoleic Acid; D008041:Linoleic Acids / Q000378:metabolism*; D008084:Lipoxygenase / Q000378:metabolism*; D006899:Mixed Function Oxygenases / Q000502:physiology*; D010084:Oxidation-Reduction
C105185:3-dodecendioic acid; D001426:Bacterial Proteins; D008041:Linoleic Acids; D019787:Linoleic Acid; D006899:Mixed Function Oxygenases; D008084:Lipoxygenase; D007535:Isomerases; D019746:Intramolecular Oxidoreductases; C021377:hydroperoxide isomerase