PathWhiz

Pathway Description

Biosynthesis of Unsaturated Fatty Acids (Tetracosanoyl-CoA)

Saccharomyces cerevisiae

Metabolic Pathway

The biosynthesis of unsaturated fatty acids begins with palmitic acid interacting with ATP and Coenzyme A through an acyl-CoA synthetase resulting in the release of AMP, diphosphate and palmitoyl-CoA. This compound then enters the cycle of unsaturated fatty acid elongation This cycle starts with the acyl-CoA reacting with a hydrogen ion and a malonyl-CoA through a 3-oxo-stearoyl-CoA synthase resulting in the release of a coenzyme A, a carbon dioxide molecule and a 3-oxoacyl-CoA. The 3-oxoacyl-CoA then reacts with a hydrogen ion and an NADPH through a 3-oxoacyl-CoA reductase resulting in the release of an NADP and a (3R)-3-hydroxy-acyl-CoA. The resulting compound then reacts with a trans-2-enoyl-CoA hydratase 2 resulting in the release of water and trans-2,3-dehydroacyl-CoA. This compound then reacts with a hydrogen ion and a NADPH through a enoyl-CoA reductase resulting in the release of a NADP and a new acyl-CoA. The cycle goes from palmitoyl-CoA-->stearoyl-CoA-->eicosanoyl-CoA-->docosanoyl-CoA-->tetracosanoyl-CoA-->hexacosanoyl-CoA. The long chain fatty acids are then incorporated into the sphingolipid pathway. The long chain fatty acid reacts with a phytosphingosine through a ceramide synthase resulting in the release of a hydrogen ion, a coenzyme A and a N-acyl-phytosphinganine.

References

Biosynthesis of Unsaturated Fatty Acids (Tetracosanoyl-CoA) References

Bagnat M, Simons K: Lipid rafts in protein sorting and cell polarity in budding yeast Saccharomyces cerevisiae. Biol Chem. 2002 Oct;383(10):1475-80. doi: 10.1515/BC.2002.169.

Pubmed: 12452424

Dickson RC, Lester RL: Sphingolipid functions in Saccharomyces cerevisiae. Biochim Biophys Acta. 2002 Jun 13;1583(1):13-25.

Pubmed: 12069845

Funato K, Vallee B, Riezman H: Biosynthesis and trafficking of sphingolipids in the yeast Saccharomyces cerevisiae. Biochemistry. 2002 Dec 24;41(51):15105-14.

Pubmed: 12484746

Dickson RC, Sumanasekera C, Lester RL: Functions and metabolism of sphingolipids in Saccharomyces cerevisiae. Prog Lipid Res. 2006 Nov;45(6):447-65. doi: 10.1016/j.plipres.2006.03.004. Epub 2006 Apr 21.

Pubmed: 16730802

Gaigg B, Toulmay A, Schneiter R: Very long-chain fatty acid-containing lipids rather than sphingolipids per se are required for raft association and stable surface transport of newly synthesized plasma membrane ATPase in yeast. J Biol Chem. 2006 Nov 10;281(45):34135-45. doi: 10.1074/jbc.M603791200. Epub 2006 Sep 15.

Pubmed: 16980694

Kohlwein SD, Eder S, Oh CS, Martin CE, Gable K, Bacikova D, Dunn T: Tsc13p is required for fatty acid elongation and localizes to a novel structure at the nuclear-vacuolar interface in Saccharomyces cerevisiae. Mol Cell Biol. 2001 Jan;21(1):109-25. doi: 10.1128/MCB.21.1.109-125.2001.

Pubmed: 11113186

Tehlivets O, Scheuringer K, Kohlwein SD: Fatty acid synthesis and elongation in yeast. Biochim Biophys Acta. 2007 Mar;1771(3):255-70. doi: 10.1016/j.bbalip.2006.07.004. Epub 2006 Jul 21.

Pubmed: 16950653

Johnson DR, Knoll LJ, Levin DE, Gordon JI: Saccharomyces cerevisiae contains four fatty acid activation (FAA) genes: an assessment of their role in regulating protein N-myristoylation and cellular lipid metabolism. J Cell Biol. 1994 Nov;127(3):751-62.

Pubmed: 7962057

Johnson DR, Knoll LJ, Rowley N, Gordon JI: Genetic analysis of the role of Saccharomyces cerevisiae acyl-CoA synthetase genes in regulating protein N-myristoylation. J Biol Chem. 1994 Jul 8;269(27):18037-46.

Pubmed: 8027063

Jones JM, Nau K, Geraghty MT, Erdmann R, Gould SJ: Identification of peroxisomal acyl-CoA thioesterases in yeast and humans. J Biol Chem. 1999 Apr 2;274(14):9216-23.

Pubmed: 10092594

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

Pubmed: 11330035

Knoll LJ, Johnson DR, Gordon JI: Biochemical studies of three Saccharomyces cerevisiae acyl-CoA synthetases, Faa1p, Faa2p, and Faa3p. J Biol Chem. 1994 Jun 10;269(23):16348-56.

Pubmed: 8206942

van Roermund CW, Ijlst L, Majczak W, Waterham HR, Folkerts H, Wanders RJ, Hellingwerf KJ: Peroxisomal fatty acid uptake mechanism in Saccharomyces cerevisiae. J Biol Chem. 2012 Jun 8;287(24):20144-53. doi: 10.1074/jbc.M111.332833. Epub 2012 Apr 9.

Pubmed: 22493507

This pathway was generated using PathWhiz - Pon, A. et al. Pathways with PathWhiz (2015) Nucleic Acids Res. 43(Web Server issue): W552–W559.

Generated from PW002403

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Visualize Compound Data

		(2E)-eicosenoyl-CoA
		(2E)-lignocerenoyl-CoA
		(2E)-Octadecenoyl-CoA
		(3R)-3-hydroxy-arachidoyl-CoA
		(3R)-3-hydroxy-docosanoyl-CoA
		(3R)-3-hydroxy-stearoyl-CoA
		(3R)-hydroxytetracosanoyl-CoA
		3-Dehydrosphinganine
		3-oxodocosanoyl-CoA
		3-oxoicosanoyl-CoA
		3-oxooctadecanoyl-CoA
		3-oxotetracosanoyl-CoA
		Adenosine monophosphate
		Adenosine triphosphate
		Carbon dioxide
		Coenzyme A
		Docosanoyl-CoA
		Eicosanoyl-CoA
		Hydrogen Ion
		L-Serine
		Malonyl-CoA
		N-tetracosanoylphytosphingosine
		NADP
		NADPH
		Oxygen
		Palmitic acid
		Palmitoyl-CoA
		Phytosphingosine
		Pyrophosphate
		Sphinganine
		Stearic acid
		Stearoyl-CoA
		Tetracosanoyl-CoA
		trans-docos-2-enoyl-CoA
		Water

Visualize Protein Data

		5-aminolevulinate synthase, mitochondrial
		Ceramide synthase subunit LIP1
		Elongation of fatty acids protein 3
		Long-chain-fatty-acid--CoA ligase 2
		Long-chain-fatty-acid--CoA ligase 2
		Long-chain-fatty-acid--CoA ligase 2
		Long-chain-fatty-acid--CoA ligase 3
		Unknown

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