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MetaCyc Pathway: oleate β-oxidation

Pathway diagram: oleate beta-oxidation

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.

Superclasses: Degradation/Utilization/Assimilation Fatty Acid and Lipids Degradation Fatty Acids Degradation

Some taxa known to possess this pathway include ? : Escherichia coli K-12 substr. MG1655

Expected Taxonomic Range: Bacteria

Oleate can serve as the sole source of carbon for Escherichia coli. Oleate is an unsaturated fatty acid and first undergoes two rounds of β-oxidation (see fatty acid β-oxidation I), producing 2-trans,5-cis-tetradecadienoyl-CoA. The original unsaturated bond is now located in the 5 position.

While the majority of 2-trans,5-cis-tetradecadienoyl-CoA is completely degraded by further rounds of β-oxidation, approximately 10% of the substrate enters a side pathway due to the production of a 3,5-unsaturated fatty acid, 3-trans,5-cis-tetradecadienoyl-CoA, from the 2,5-unsaturated 2-trans,5-cis-tetradecadienoyl-CoA by the enoyl-CoA isomerase activity of FadB. 3-trans,5-cis-tetradecadienoyl-CoA can not be further metabolized by Escherichia coli, since the organism lacks a Delta;3,52,4-dienoyl-CoA isomerase activity. Thioesterase III liberates the CoA moiety from 3-trans,5-cis-tetradecadienoyl-CoA by hydrolysis, thus avoiding the production of a dead-end compound that traps CoA. The resulting (3E,5Z)-tetradecadienoate is secreted into the growth medium [Ren04, Nie08a].

Review: Clark, D.P. and Cronan, J.E., Two-Carbon Compounds and Fatty Acids as Carbon Sources, EcoSal Module 3.4.4 [ECOSAL]

Variants: 9-cis, 11-trans-octadecadienoyl-CoA degradation (isomerase-dependent, yeast) , 10-cis-heptadecenoyl-CoA degradation (yeast) , 10-trans-heptadecenoyl-CoA degradation (MFE-dependent, yeast) , 10-trans-heptadecenoyl-CoA degradation (reductase-dependent, yeast) , alkane oxidation , fatty acid α-oxidation I , fatty acid α-oxidation II , fatty acid α-oxidation III , fatty acid β-oxidation (peroxisome, yeast) , fatty acid β-oxidation I , fatty acid β-oxidation II (peroxisome) , fatty acid β-oxidation III (unsaturated, odd number) , fatty acid beta-oxidation V (unsaturated, odd number, di-isomerase-dependent) , fatty acid β-oxidation VI (peroxisome) , oleate β-oxidation (isomerase-dependent, yeast) , oleate β-oxidation (reductase-dependent, yeast) , oleate β-oxidation (thioesterase-dependent, yeast) , unsaturated, even numbered fatty acid β-oxidation

Unification Links: EcoCyc:PWY0-1337

Created 30-Jun-2008 by Keseler I , SRI International


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

Nie08a: Nie L, Ren Y, Schulz H (2008). "Identification and characterization of Escherichia coli thioesterase III that functions in fatty acid beta-oxidation." Biochemistry 47(29);7744-51. PMID: 18576672

Ren04: Ren Y, Aguirre J, Ntamack AG, Chu C, Schulz H (2004). "An alternative pathway of oleate beta-oxidation in Escherichia coli involving the hydrolysis of a dead end intermediate by a thioesterase." J Biol Chem 279(12);11042-50. PMID: 14707139

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

Binstock81: Binstock JF, Schulz H (1981). "Fatty acid oxidation complex from Escherichia coli." Methods Enzymol 1981;71 Pt C;403-11. PMID: 7024730

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

Feng09a: Feng Y, Cronan JE (2009). "A new member of the Escherichia coli fad regulon: transcriptional regulation of fadM (ybaW)." J Bacteriol 191(20);6320-8. PMID: 19684132

Geisbrecht98: Geisbrecht BV, Zhu D, Schulz K, Nau K, Morrell JC, Geraghty M, Schulz H, Erdmann R, Gould SJ (1998). "Molecular characterization of Saccharomyces cerevisiae Delta3, Delta2-enoyl-CoA isomerase." J Biol Chem 273(50);33184-91. PMID: 9837886

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."

Gurvitz98: Gurvitz A, Mursula AM, Firzinger A, Hamilton B, Kilpelainen SH, Hartig A, Ruis H, Hiltunen JK, Rottensteiner H (1998). "Peroxisomal Delta3-cis-Delta2-trans-enoyl-CoA isomerase encoded by ECI1 is required for growth of the yeast Saccharomyces cerevisiae on unsaturated fatty acids." J Biol Chem 273(47);31366-74. PMID: 9813046

He96a: He XY, Yang SY (1996). "Histidine-450 is the catalytic residue of L-3-hydroxyacyl coenzyme A dehydrogenase associated with the large alpha-subunit of the multienzyme complex of fatty acid oxidation from Escherichia coli." Biochemistry 1996;35(29);9625-30. PMID: 8755745

Jones99a: Jones JM, Nau K, Geraghty MT, Erdmann R, Gould SJ (1999). "Identification of peroxisomal acyl-CoA thioesterases in yeast and humans." J Biol Chem 274(14);9216-23. PMID: 10092594

Kal00: Kal AJ, Hettema EH, van den Berg M, Koerkamp MG, van Ijlst L, Distel B, Tabak HF (2000). "In silicio search for genes encoding peroxisomal proteins in Saccharomyces cerevisiae." Cell Biochem Biophys 32 Spring;1-8. PMID: 11330035

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

Maeda06: Maeda I, Delessert S, Hasegawa S, Seto Y, Zuber S, Poirier Y (2006). "The peroxisomal Acyl-CoA thioesterase Pte1p from Saccharomyces cerevisiae is required for efficient degradation of short straight chain and branched chain fatty acids." J Biol Chem 281(17);11729-35. PMID: 16490786

Mursula01: Mursula AM, van Aalten DM, Hiltunen JK, Wierenga RK (2001). "The crystal structure of delta(3)-delta(2)-enoyl-CoA isomerase." J Mol Biol 309(4);845-53. PMID: 11399063

Mursula04: Mursula AM, Hiltunen JK, Wierenga RK (2004). "Structural studies on delta(3)-delta(2)-enoyl-CoA isomerase: the variable mode of assembly of the trimeric disks of the crotonase superfamily." FEBS Lett 557(1-3);81-7. PMID: 14741345

Nie08: Nie L, Ren Y, Janakiraman A, Smith S, Schulz H (2008). "A novel paradigm of fatty acid beta-oxidation exemplified by the thioesterase-dependent partial degradation of conjugated linoleic acid that fully supports growth of Escherichia coli." Biochemistry 47(36);9618-26. PMID: 18702504

Ntamack09: Ntamack AG, Karpichev IV, Gould SJ, Small GM, Schulz H (2009). "Oleate beta-oxidation in yeast involves thioesterase but not Yor180c protein that is not a dienoyl-CoA isomerase." Biochim Biophys Acta 1791(5);371-8. PMID: 19830908

Pawar81: Pawar S, Schulz H (1981). "The structure of the multienzyme complex of fatty acid oxidation from Escherichia coli." J Biol Chem 1981;256(8);3894-9. PMID: 7012144

Pramanik79: Pramanik A, Pawar S, Antonian E, Schulz H (1979). "Five different enzymatic activities are associated with the multienzyme complex of fatty acid oxidation from Escherichia coli." J Bacteriol 1979;137(1);469-73. PMID: 368024

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

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Please cite the following article in publications resulting from the use of MetaCyc: Caspi et al, Nucleic Acids Research 42:D459-D471 2014
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