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MetaCyc Pathway: poly-hydroxy fatty acids biosynthesis

Pathway diagram: poly-hydroxy fatty acids biosynthesis

This view shows enzymes only for those organisms listed below, in the list of taxa known to possess the 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 Hydroxylated Fatty Acids 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

Bi13: Bi H, Wang H, Cronan JE (2013). "FabQ, a dual-function dehydratase/isomerase, circumvents the last step of the classical fatty acid synthesis cycle." Chem Biol 20(9);1157-67. PMID: 23972938

Biebl02: Biebl H, Sproer C (2002). "Taxonomy of the glycerol fermenting clostridia and description of Clostridium diolis sp. nov." Syst Appl Microbiol 25(4);491-7. PMID: 12583708

Goldfine71: Goldfine H, Panos C (1971). "Phospholipids of Clostridium butyricum. IV. Analysis of the positional isomers of monounsaturated and cyclopropane fatty acids and alk-1'-enyl ethers by capillary column chromatography." J Lipid Res 12(2);214-20. PMID: 5554109

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

Johnston83: Johnston NC, Goldfine H (1983). "Lipid composition in the classification of the butyric acid-producing clostridia." J Gen Microbiol 129(4);1075-81. PMID: 6886674

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

Lederer94: Lederer F (1994). "The cytochrome b5-fold: an adaptable module." Biochimie 76(7);674-92. PMID: 7893819

Lee98a: 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

Napier03: Napier JA, Michaelson LV, Sayanova O (2003). "The role of cytochrome b5 fusion desaturases in the synthesis of polyunsaturated fatty acids." Prostaglandins Leukot Essent Fatty Acids 68(2);135-43. PMID: 12538077

Scheuerbrandt61: Scheuerbrandt G, Goldfine H, Baronowsky PE, Bloch K (1961). "A novel mechanism for the biosynthesis of unsaturated fatty acids." J Biol Chem 236;PC70-PC71. PMID: 14498314


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 19.0 on Sun Aug 30, 2015, biocyc14.