Metabolic Modeling Tutorial
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Metabolic Modeling Tutorial
discounted EARLY registration ends Dec 31, 2014
Metabolic Modeling Tutorial
discounted EARLY registration ends Dec 31, 2014
Metabolic Modeling Tutorial
discounted EARLY registration ends Dec 31, 2014
Metabolic Modeling Tutorial
discounted EARLY registration ends Dec 31, 2014
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MetaCyc Pathway: poly-hydroxy fatty acids biosynthesis

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 Acids and Lipids Biosynthesis Fatty Acid Biosynthesis

Some taxa known to possess this pathway include ? : Arabidopsis thaliana col

Expected Taxonomic Range: Viridiplantae

Summary:
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].

Credits:
Created 08-Feb-2011 by Zhang P , TAIR


References

Hou00: Hou, CT, Forman, RJ (2000). "Growth inhibition of plant pathogenic fungi by hydroxy fatty acids." J Ind Microbiol Biotechnol, 24:275-276.

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

Other References Related to Enzymes, Genes, Subpathways, and Substrates of this Pathway

Bedord78: Bedord CJ, McMahon V, Adams B (1978). "alpha-linolenic acid biosynthesis in Cyanidium caldarium." Arch Biochem Biophys 185(1);15-20. PMID: 414660

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

Kenyon72: Kenyon CN (1972). "Fatty acid composition of unicellular strains of blue-green algae." J Bacteriol 109(2);827-34. PMID: 4621688

Latendresse13: Latendresse M. (2013). "Computing Gibbs Free Energy of Compounds and Reactions in MetaCyc."

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


Report Errors or Provide Feedback
Please cite the following article in publications resulting from the use of MetaCyc: Caspi et al, Nucleic Acids Research 42:D459-D471 2014
Page generated by SRI International Pathway Tools version 18.5 on Wed Nov 26, 2014, BIOCYC13B.