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discounted EARLY registration ends Dec 31, 2014
BioCyc websites down
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discounted EARLY registration ends Dec 31, 2014
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MetaCyc Pathway: fatty acid beta-oxidation V (unsaturated, odd number, di-isomerase-dependent)

Enzyme View:

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 ? : Arabidopsis thaliana col , Saccharomyces cerevisiae

Expected Taxonomic Range: Opisthokonta , Viridiplantae

Summary:
This is an alternative degradation route of fatty acids with cis-double bonds on odd-number carbons, for example, oleate, that was proposed after the identification of a delta3,5-delta2,4-dienoyl-CoA isomerase from yeast [Gurvitz99]. The physiological role of the yeast DCI1 however remains unclear since yeast mutants with a deletion in DCI1 showed no deficiency in utilization of oleate [Gurvitz99]. Later, this pathway was thought to be present in Arabidopsis based on the identification of the Arabidopsis DCI1 [Goepfert05, Goepfert07]. No genetics data are available for the Arabidopsis DCI1 thus its physiological role in fatty acid degradation is still unclear.

In this pathway, unsaturated fatty acids with cis-double bonds on odd-number carbons (i.e. a double bond on the 9th position in the case of oleate) are converted to cis-5-enoyl-CoA after two rounds of core beta oxidation cycle. Instead of continuing for another round of core beta-oxidation cycle which would yield cis-3-enoyl-CoA to enter fatty acid β-oxidation III (unsaturated, odd number), cis-5-enoyl-CoA once being oxidized to trans-2,cis-5-dienoyl-CoA exits the core beta oxidation. It is converted to trans-3,cis-5-dienoyl-CoA by delta3,delta2-enoyl-CoA isomerase. Trans-3,cis-5-dienoyl-CoA is then converted by the di-isomerase delta3,5-delta2,4-dienoyl-CoA isomerase to trans-2,trans-4-dienoyl-CoA. The latter is further converted to trans-3-enoyl-CoA by 2,4-dienoyl-CoA reductase. Finally, trans-3-enoyl-CoA is converted to trans-2-enoyl-CoA to reenter core beta oxidation for complete degradation.

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 β-oxidation VI (peroxisome) , oleate β-oxidation , 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

Credits:
Created 20-Jul-2011 by Zhang P , PMN


References

Goepfert05: Goepfert S, Vidoudez C, Rezzonico E, Hiltunen JK, Poirier Y (2005). "Molecular identification and characterization of the Arabidopsis delta(3,5),delta(2,4)-dienoyl-coenzyme A isomerase, a peroxisomal enzyme participating in the beta-oxidation cycle of unsaturated fatty acids." Plant Physiol 138(4);1947-56. PMID: 16040662

Goepfert07: Goepfert S, Poirier Y (2007). "Beta-oxidation in fatty acid degradation and beyond." Curr Opin Plant Biol 10(3);245-51. PMID: 17434787

Gurvitz99: Gurvitz A, Mursula AM, Yagi AI, Hartig A, Ruis H, Rottensteiner H, Hiltunen JK (1999). "Alternatives to the isomerase-dependent pathway for the beta-oxidation of oleic acid are dispensable in Saccharomyces cerevisiae. Identification of YOR180c/DCI1 encoding peroxisomal delta(3,5)-delta(2,4)-dienoyl-CoA isomerase." J Biol Chem 274(35);24514-21. PMID: 10455114

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

Coe92: Coe JG, Murray LE, Kennedy CJ, Dawes IW (1992). "Isolation and characterization of sporulation-specific promoters in the yeast Saccharomyces cerevisiae." Mol Microbiol 6(1);75-81. PMID: 1738316

Dmochowska90: Dmochowska A, Dignard D, Maleszka R, Thomas DY (1990). "Structure and transcriptional control of the Saccharomyces cerevisiae POX1 gene encoding acyl-coenzyme A oxidase." Gene 88(2);247-52. PMID: 2189786

Eastmond00a: Eastmond PJ, Hooks MA, Williams D, Lange P, Bechtold N, Sarrobert C, Nussaume L, Graham IA (2000). "Promoter trapping of a novel medium-chain acyl-CoA oxidase, which is induced transcriptionally during Arabidopsis seed germination." J Biol Chem 275(44);34375-81. PMID: 10918060

Engeland91: Engeland K, Kindl H (1991). "Purification and characterization of a plant peroxisomal delta 2, delta 3-enoyl-CoA isomerase acting on 3-cis-enoyl-CoA and 3-trans-enoyl-CoA." Eur J Biochem 196(3);699-705. PMID: 2013292

Froman00: Froman BE, Edwards PC, Bursch AG, Dehesh K (2000). "ACX3, a novel medium-chain acyl-coenzyme A oxidase from Arabidopsis." Plant Physiol 123(2);733-42. PMID: 10859203

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

Geisbrecht99: Geisbrecht BV, Schulz K, Nau K, Geraghty MT, Schulz H, Erdmann R, Gould SJ (1999). "Preliminary characterization of Yor180Cp: identification of a novel peroxisomal protein of saccharomyces cerevisiae involved in fatty acid metabolism." Biochem Biophys Res Commun 260(1);28-34. PMID: 10381339

Goepfert08: Goepfert S, Vidoudez C, Tellgren-Roth C, Delessert S, Hiltunen JK, Poirier Y (2008). "Peroxisomal Delta(3),Delta(2)-enoyl CoA isomerases and evolution of cytosolic paralogues in embryophytes." Plant J 56(5);728-42. PMID: 18657232

GuhnemannSchafe95: Guhnemann-Schafer K, Kindl H (1995). "Fatty acid beta-oxidation in glyoxysomes. Characterization of a new tetrafunctional protein (MFP III)." Biochim Biophys Acta 1256(2);181-6. PMID: 7766696

GuhnemannShafer94: Guhnemann-Shafer, Kerstin, Engeland, Kurt, Linder, Dietmar, Kindl, Helmut (1994). "Evidence for domain structures of the trifunctional protein and tetrafunctional protein acting in glyoxysomal fatty acid beta-oxidation." Eur J Biochem, 226: 909-915.

Gurvitz00: Gurvitz A, Wabnegger L, Rottensteiner H, Dawes IW, Hartig A, Ruis H, Hamilton B (2000). "Adr1p-dependent regulation of the oleic acid-inducible yeast gene SPS19 encoding the peroxisomal beta-oxidation auxiliary enzyme 2,4-dienoyl-CoA reductase." Mol Cell Biol Res Commun 4(2);81-9. PMID: 11170837

Gurvitz01: Gurvitz A, Hiltunen JK, Erdmann R, Hamilton B, Hartig A, Ruis H, Rottensteiner H (2001). "Saccharomyces cerevisiae Adr1p governs fatty acid beta-oxidation and peroxisome proliferation by regulating POX1 and PEX11." J Biol Chem 276(34);31825-30. PMID: 11431484

Gurvitz97: Gurvitz A, Rottensteiner H, Kilpelainen SH, Hartig A, Hiltunen JK, Binder M, Dawes IW, Hamilton B (1997). "The Saccharomyces cerevisiae peroxisomal 2,4-dienoyl-CoA reductase is encoded by the oleate-inducible gene SPS19." J Biol Chem 272(35);22140-7. PMID: 9268358

Gurvitz97a: Gurvitz A, Rottensteiner H, Hiltunen JK, Binder M, Dawes IW, Ruis H, Hamilton B (1997). "Regulation of the yeast SPS19 gene encoding peroxisomal 2,4-dienoyl-CoA reductase by the transcription factors Pip2p and Oaf1p: beta-oxidation is dispensable for Saccharomyces cerevisiae sporulation in acetate medium." Mol Microbiol 26(4);675-85. PMID: 9427398

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

Hayashi99: Hayashi H, De Bellis L, Ciurli A, Kondo M, Hayashi M, Nishimura M (1999). "A novel acyl-CoA oxidase that can oxidize short-chain acyl-CoA in plant peroxisomes." J Biol Chem 274(18);12715-21. PMID: 10212254

Karpichev00: Karpichev IV, Small GM (2000). "Evidence for a novel pathway for the targeting of a Saccharomyces cerevisiae peroxisomal protein belonging to the isomerase/hydratase family." J Cell Sci 113 ( Pt 3);533-44. PMID: 10639339

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

Luo96: Luo Y, Karpichev IV, Kohanski RA, Small GM (1996). "Purification, identification, and properties of a Saccharomyces cerevisiae oleate-activated upstream activating sequence-binding protein that is involved in the activation of POX1." J Biol Chem 271(20);12068-75. PMID: 8662598

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

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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 18.5 on Mon Dec 22, 2014, BIOCYC14B.