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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 Unusual 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

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

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

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."

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


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 May 24, 2015, biocyc11.