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MetaCyc Pathway: cis-vaccenate biosynthesis
Inferred from experiment

Enzyme View:

Pathway diagram: cis-vaccenate 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: cis vaccenic acid acid biosynthesis

Superclasses: BiosynthesisFatty Acid and Lipid BiosynthesisFatty Acid BiosynthesisUnsaturated Fatty Acid Biosynthesis

Some taxa known to possess this pathway include : Asclepias syriaca, Dolichandra unguis-cati, Escherichia coli K-12 substr. MG1655

Expected Taxonomic Range: Bacteria , Magnoliophyta

The only unsaturated fatty acids found in Escherichia coli, palmitoleate and cis-vaccenate, comprise about one-half the fatty acid content of the organism. The proportion of unsaturated fatty acids is known to increase in Escherichia coli with lower growth temperature, a phenomenon found in most organisms that provides a mechanism for adjusting the lipid phase transition of the membrane phospholipids to differing temperatures.

KASII is the only enzyme that can catalyze the conversion of palmitoleate to cis-vaccenate, and is believed to play a major role in the thermal regulation of fatty acid composition of the membrane phospholipids of Escherichia coli [Garwin80a]. KASII is one of three β-ketoacyl-ACP synthases (KAS) in Escherichia coli: KASI, KASII and KASIII, encoded by fabB, fabF and fabH, respectively.

It has been shown that KASII is more active at low temperatures (relative to the overall rate of fatty acid synthesis) than at high temperatures [Garwin80]. This relative increase results in the production of cis-vaccenate rather than palmitoleate. Furthermore, because the former (but not the later) can be incorporated into both positions of sn-glycerol 3-phosphate, the synthesis of diunsaturated phospholipids occurs and the thermotrophic phase transition of the membrane phospholipids is lowered [Garwin80a].

Some plant species such as Asclepias syriaca and Dolichandra unguis-cati (Doxantha unguis-cati L.) produce relatively high levels of palmitoleate and cis-vaccenate in their seed oils [Chisholm60, Chisholm65]. The plastidal synthesis of cis-vaccenate from palmitoleate via KASII is thought to be similar to that of the Escherichia coli pathway (in [Nguyen10b]). KAS II enzymes (EC have been characterized in Brassica napus [Han01a] and Spinacia oleracea [Shimakata82], and a NADH-dependent enoyl-ACP reductase (EC has been characterized in these and several other plant species [Shimakata82, Kater91, Caughey82, Shimakata82a].

Superpathways: superpathway of fatty acids biosynthesis (E. coli), superpathway of unsaturated fatty acids biosynthesis (E. coli)

Variants: (5Z)-dodec-5-enoate biosynthesis, (5Z)-icosenoate biosynthesis, 10,13-epoxy-11-methyl-octadecadienoate biosynthesis, gondoate biosynthesis (anaerobic), petroselinate biosynthesis, ricinoleate biosynthesis, sapienate biosynthesis, vernolate biosynthesis I, vernolate biosynthesis II

Unification Links: EcoCyc:PWY-5973

Created 11-Jul-2008 by Caspi R, SRI International
Revised 13-May-2013 by Fulcher CA, SRI International


Caughey82: Caughey I, Kekwick RG (1982). "The characteristics of some components of the fatty acid synthetase system in the plastids from the mesocarp of avocado (Persea americana) fruit." Eur J Biochem 123(3);553-61. PMID: 7075600

Chisholm60: Chisholm MJ, Hopkins C Y (1960). "11-octadecenoic acid and other fatty acids of Asclepias syriaca seed oil." Canadian Journal of Chemistry 38(6);805-812.

Chisholm65: Chisholm MJ, Hopkins C Y (1965). "Fatty acids of doxantha seed oil." Journal of the American Oil Chemists' Society 42(1);49-50.

Garwin80: Garwin JL, Klages AL, Cronan JE (1980). "Structural, enzymatic, and genetic studies of beta-ketoacyl-acyl carrier protein synthases I and II of Escherichia coli." J Biol Chem 1980;255(24);11949-56. PMID: 7002930

Garwin80a: Garwin JL, Klages AL, Cronan JE (1980). "Beta-ketoacyl-acyl carrier protein synthase II of Escherichia coli. Evidence for function in the thermal regulation of fatty acid synthesis." J Biol Chem 1980;255(8);3263-5. PMID: 6988423

Han01a: Han J, Luhs W, Sonntag K, Zahringer U, Borchardt DS, Wolter FP, Heinz E, Frentzen M (2001). "Functional characterization of beta-ketoacyl-CoA synthase genes from Brassica napus L." Plant Mol Biol 46(2);229-39. PMID: 11442062

Kater91: Kater MM, Koningstein GM, Nijkamp HJ, Stuitje AR (1991). "cDNA cloning and expression of Brassica napus enoyl-acyl carrier protein reductase in Escherichia coli." Plant Mol Biol 17(4);895-909. PMID: 1912503

Nguyen10b: Nguyen HT, Mishra G, Whittle E, Pidkowich MS, Bevan SA, Merlo AO, Walsh TA, Shanklin J (2010). "Metabolic engineering of seeds can achieve levels of omega-7 fatty acids comparable with the highest levels found in natural plant sources." Plant Physiol 154(4);1897-904. PMID: 20943853

Shimakata82: Shimakata T, Stumpf PK (1982). "Purification and characterizations of beta-Ketoacyl-[acyl-carrier-protein] reductase, beta-hydroxyacyl-[acyl-carrier-protein] dehydrase, and enoyl-[acyl-carrier-protein] reductase from Spinacia oleracea leaves." Arch Biochem Biophys 218(1);77-91. PMID: 6756317

Shimakata82a: Shimakata T, Stumpf PK (1982). "The procaryotic nature of the fatty acid synthetase of developing Carthamus tinctorius L. (Safflower) seeds." Arch Biochem Biophys 217(1);144-54. PMID: 7125663

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

Baldock96: Baldock C, Rafferty JB, Sedelnikova SE, Baker PJ, Stuitje AR, Slabas AR, Hawkes TR, Rice DW (1996). "A mechanism of drug action revealed by structural studies of enoyl reductase." Science 274(5295);2107-10. PMID: 8953047

Barnes68: Barnes EM, Wakil SJ (1968). "Studies on the mechanism of fatty acid synthesis. XIX. Preparation and general properties of palmityl thioesterase." J Biol Chem 1968;243(11);2955-62. PMID: 4871199

Bergler92: Bergler H, Hogenauer G, Turnowsky F (1992). "Sequences of the envM gene and of two mutated alleles in Escherichia coli." J Gen Microbiol 1992;138 ( Pt 10);2093-100. PMID: 1364817

Bergler94: Bergler H, Wallner P, Ebeling A, Leitinger B, Fuchsbichler S, Aschauer H, Kollenz G, Hogenauer G, Turnowsky F (1994). "Protein EnvM is the NADH-dependent enoyl-ACP reductase (FabI) of Escherichia coli." J Biol Chem 1994;269(8);5493-6. PMID: 8119879

Bergler96: Bergler H, Fuchsbichler S, Hogenauer G, Turnowsky F (1996). "The enoyl-[acyl-carrier-protein] reductase (FabI) of Escherichia coli, which catalyzes a key regulatory step in fatty acid biosynthesis, accepts NADH and NADPH as cofactors and is inhibited by palmitoyl-CoA." Eur J Biochem 242(3);689-94. PMID: 9022698

Bonner72: Bonner WM, Bloch K (1972). "Purification and properties of fatty acyl thioesterase I from Escherichia coli." J Biol Chem 1972;247(10);3123-33. PMID: 4554913

Butland05: Butland G, Peregrin-Alvarez JM, Li J, Yang W, Yang X, Canadien V, Starostine A, Richards D, Beattie B, Krogan N, Davey M, Parkinson J, Greenblatt J, Emili A (2005). "Interaction network containing conserved and essential protein complexes in Escherichia coli." Nature 433(7025);531-7. PMID: 15690043

Byers07: Byers DM, Gong H (2007). "Acyl carrier protein: structure-function relationships in a conserved multifunctional protein family." Biochem Cell Biol 85(6);649-62. PMID: 18059524

Campbell01: Campbell JW, Cronan JE (2001). "Bacterial fatty acid biosynthesis: targets for antibacterial drug discovery." Annu Rev Microbiol 55;305-32. PMID: 11544358

Chan10a: Chan DI, Vogel HJ (2010). "Current understanding of fatty acid biosynthesis and the acyl carrier protein." Biochem J 430(1);1-19. PMID: 20662770

Cho94: Cho H, Cronan JE (1994). ""Protease I" of Escherichia coli functions as a thioesterase in vivo." J Bacteriol 176(6);1793-5. PMID: 8132479

Cho95: Cho H, Cronan JE (1995). "Defective export of a periplasmic enzyme disrupts regulation of fatty acid synthesis." J Biol Chem 270(9);4216-9. PMID: 7876180

DAgnolo75: D'Agnolo G, Rosenfeld IS, Vagelos PR (1975). "Multiple forms of beta-ketoacyl-acyl carrier protein synthetase in Escherichia coli." J Biol Chem 250(14);5289-94. PMID: 237914

DiazMejia09: Diaz-Mejia JJ, Babu M, Emili A (2009). "Computational and experimental approaches to chart the Escherichia coli cell-envelope-associated proteome and interactome." FEMS Microbiol Rev 33(1);66-97. PMID: 19054114

ECOSAL: EcoSal "Escherichia coli and Salmonella: Cellular and Molecular Biology." Online edition.

Edwards97a: Edwards P, Nelsen JS, Metz JG, Dehesh K (1997). "Cloning of the fabF gene in an expression vector and in vitro characterization of recombinant fabF and fabB encoded enzymes from Escherichia coli." FEBS Lett 402(1);62-6. PMID: 9013860

Escaich11: Escaich S, Prouvensier L, Saccomani M, Durant L, Oxoby M, Gerusz V, Moreau F, Vongsouthi V, Maher K, Morrissey I, Soulama-Mouze C (2011). "The MUT056399 inhibitor of FabI is a new antistaphylococcal compound." Antimicrob Agents Chemother 55(10);4692-7. PMID: 21825292

GOA01: GOA, MGI (2001). "Gene Ontology annotation based on Enzyme Commission mapping." Genomics 74;121-128.

GOA01a: GOA, DDB, FB, MGI, ZFIN (2001). "Gene Ontology annotation through association of InterPro records with GO terms."

GOA06: GOA, SIB (2006). "Electronic Gene Ontology annotations created by transferring manual GO annotations between orthologous microbial proteins."

Showing only 20 references. To show more, press the button "Show all references".

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 Pathway Tools version 19.5 (software by SRI International) on Wed May 4, 2016, biocyc13.