Note: a dashed line (without arrowheads) between two compound names is meant to imply that the two names are just different instantiations of the same compound -- i.e. one may be a specific name and the other a general name, or they may both represent the same compound in different stages of a polymerization-type pathway. If an enzyme name is shown in bold, there is experimental evidence for this enzymatic activity.
Synonyms: free fatty acid epoxidation via a P450
|Superclasses:||Biosynthesis → Fatty Acid and Lipid Biosynthesis → Fatty Acid Biosynthesis → Unusual Fatty Acid Biosynthesis|
Some taxa known to possess this pathway include : Arabidopsis thaliana col
Expected Taxonomic Range: Viridiplantae
An Arabidopsis cytochrome P450, CYP77A4, was shown to catalyze expoxidation of free fatty acids, the first one of its kind characterized in plants [Sauveplane09]. The epoxides can be further metabolized by epoxide hydrolases and fatty acid hydroxylases to diols and poly-hydroxy fatty acids. Some of the derived metabolites are cutin monomers, i.e. 18-hydroxy-9,10-epoxystearate (see cutin biosynthesis), some others have antifungal properties possibly involved in plant defense, i.e. 12,13,17-trihydroxyoctadeca-9-enoate [Hou00].
Sauveplane09: Sauveplane V, Kandel S, Kastner PE, Ehlting J, Compagnon V, Werck-Reichhart D, Pinot F (2009). "Arabidopsis thaliana CYP77A4 is the first cytochrome P450 able to catalyze the epoxidation of free fatty acids in plants." FEBS J 276(3);719-35. PMID: 19120447
Blee93: Blee E, Stahl U, Schuber F, Stymne S (1993). "Regio- and stereoselectivity of cytochrome P-450 and peroxygenase-dependent formation of cis-12,13-epoxy-9(Z)-octadecenoic acid (vernolic acid) in Euphorbia lagascae." Biochem Biophys Res Commun 197(2);778-84. PMID: 8267615
Jaworski74: Jaworski JG, Stumpf PK (1974). "Fat metabolism in higher plants. Properties of a soluble stearyl-acyl carrier protein desaturase from maturing Carthamus tinctorius." Arch Biochem Biophys 162(1);158-65. PMID: 4831331
Le01: Le Bouquin R, Skrabs M, Kahn R, Benveniste I, Salaun JP, Schreiber L, Durst F, Pinot F (2001). "CYP94A5, a new cytochrome P450 from Nicotiana tabacum is able to catalyze the oxidation of fatty acids to the omega-alcohol and to the corresponding diacid." Eur J Biochem 268(10);3083-90. PMID: 11358528
Lee98: Lee M, Lenman M, Banas A, Bafor M, Singh S, Schweizer M, Nilsson R, Liljenberg C, Dahlqvist A, Gummeson PO, Sjodahl S, Green A, Stymne S (1998). "Identification of non-heme diiron proteins that catalyze triple bond and epoxy group formation." Science 280(5365);915-8. PMID: 9572738
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