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MetaCyc Pathway: dimorphecolate biosynthesis

Pathway diagram: dimorphecolate 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: dimorphecolic acid biosynthesis

Superclasses: Biosynthesis Fatty Acid and Lipid Biosynthesis Fatty Acid Biosynthesis Unsaturated Fatty Acid Biosynthesis Polyunsaturated Fatty Acid Biosynthesis Conjugated Fatty Acid Biosynthesis

Some taxa known to possess this pathway include ? : Dimorphotheca sinuata

Expected Taxonomic Range: Magnoliophyta

Summary:
Dimorphecolate (9-OH-18:2Δ10trans,12trans) is the major fatty acid found in seeds of Dimorphotheca species. It is a conjugated fatty acid that has three unusual structural features:

1) a C-9 hydroxyl group

2) conjugated Δ10,Δ12 double bonds, and

3) two trans double bonds, rather than the much more common cis bonds.

This special fatty acid has potential values in industrial applications such as the manufacture of paints, inks, lubricants, plastics, and nylon.

Dimorphecolate is derived from oleate by the concerted activity of two desaturase enzymes, encoded by the FAD2-1 and FAD2-2 genes [Cahoon04].

cDNAs of both enzymes have been cloned. Ectopic expression in yeast and soybean somatic embryo cells demonstrated that FAD2-1 encodes a oleate 12(E)-desaturase, able to convert oleate (18:1Δ9cis) to (9Z,12E)-octadecadienoate (18:2Δ9cis,12trans). The ectopic expression experiments also demonstrated that FAD2-2 encodes a Δ9 fatty acid conjugase-like enzyme that is able to introduce a hydroxyl group at C9 while simultaneously converting the cis Δ9 double bond to a trans Δ10 double bond [Cahoon04].

Credits:
Created 05-Oct-2006 by Zhang P , TAIR
Revised 01-Dec-2014 by Caspi R , SRI International


References

Cahoon04: Cahoon EB, Kinney AJ (2004). "Dimorphecolic acid is synthesized by the coordinate activities of two divergent Delta12-oleic acid desaturases." J Biol Chem 279(13);12495-502. PMID: 14718523

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

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

Dyer02: Dyer JM, Chapital DC, Kuan JC, Mullen RT, Turner C, McKeon TA, Pepperman AB (2002). "Molecular analysis of a bifunctional fatty acid conjugase/desaturase from tung. Implications for the evolution of plant fatty acid diversity." Plant Physiol 130(4);2027-38. PMID: 12481086

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

Lager13: Lager I, Yilmaz JL, Zhou XR, Jasieniecka K, Kazachkov M, Wang P, Zou J, Weselake R, Smith MA, Bayon S, Dyer JM, Shockey JM, Heinz E, Green A, Banas A, Stymne S (2013). "Plant acyl-CoA:lysophosphatidylcholine acyltransferases (LPCATs) have different specificities in their forward and reverse reactions." J Biol Chem 288(52);36902-14. PMID: 24189065

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

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

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

Rubio06: Rubio S, Larson TR, Gonzalez-Guzman M, Alejandro S, Graham IA, Serrano R, Rodriguez PL (2006). "An Arabidopsis mutant impaired in coenzyme A biosynthesis is sugar dependent for seedling establishment." Plant Physiol 140(3);830-43. PMID: 16415216

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 Wed Jul 1, 2015, BIOCYC13A.