Reaction: a fatty acid + O2 = a (2R)-2-hydroperoxyfatty acid
Other name(s): DOX1 (gene name)
Systematic name: fatty acid:oxygen 2-oxidoreductase [(2R)-2-hydroperoxyfatty acid-forming]
Comments: Contains heme. This plant enzyme catalyses the (2R)-hydroperoxidation of fatty acids. It differs from lipoxygenases and cyclooxygenases in that the oxygen addition does not target an unsaturated region in the fatty acid. In vitro the product undergoes spontaneous decarboxylation, resulting in formation of a chain-shortened aldehyde. In vivo the product may be reduced to a (2R)-2-hydroxyfatty acid. The enzyme, which is involved in responses to different abiotic and biotic stresses, has a wide substrate range that includes both saturated and unsaturated fatty acids.
Links to other databases: BRENDA, EXPASY, KEGG, MetaCyc, CAS registry number:
1. Akakabe, Y., Matsui, K., and Kajiwara, T. Enantioselective α-hydroperoxylation of long-chain fatty acids with crude enzyme of marine green alga Ulva pertusa. Tetrahedron Lett. 40 (1999) 1137-1140.
2. Hamberg, M., Sanz, A. and Castresana, C. α-oxidation of fatty acids in higher plants. Identification of a pathogen-inducible oxygenase (piox) as an α-dioxygenase and biosynthesis of 2-hydroperoxylinolenic acid. J. Biol. Chem. 274 (1999) 24503-24513. [PMID: 10455113]
3. Saffert, A., Hartmann-Schreier, J., Schon, A. and Schreier, P. A dual function α-dioxygenase-peroxidase and NAD(+) oxidoreductase active enzyme from germinating pea rationalizing α-oxidation of fatty acids in plants. Plant Physiol. 123 (2000) 1545-1552. [PMID: 10938370]
4. Koeduka, T., Matsui, K., Akakabe, Y. and Kajiwara, T. Catalytic properties of rice α-oxygenase. A comparison with mammalian prostaglandin H synthases. J. Biol. Chem. 277 (2002) 22648-22655. [PMID: 11909851]
5. Liu, W., Rogge, C.E., Bambai, B., Palmer, G., Tsai, A.L. and Kulmacz, R.J. Characterization of the heme environment in Arabidopsis thaliana fatty acid α-dioxygenase-1. J. Biol. Chem. 279 (2004) 29805-29815. [PMID: 15100225]
6. Meisner, A.K., Saffert, A., Schreier, P. and Schon, A. Fatty acid α-dioxygenase from Pisum sativum: temporal and spatial regulation during germination and plant development. J. Plant Physiol. 166 (2009) 333-343. [PMID: 18760499]