3D,7D,11D-Phytanic acid (BioDeep_00000019509)
Main id: BioDeep_00000004722
Secondary id: BioDeep_00000871729
human metabolite Endogenous Volatile Flavor Compounds
代谢物信息卡片
3,7,11,15-Tetramethyl-[3R-(3R*,7R*,11R*)]-hexadecanoic acid
化学式: C20H40O2 (312.302814)
中文名称: 植烷酸
谱图信息:
最多检出来源 Homo sapiens(feces) 40%
分子结构信息
SMILES: CC(C)CCCC(C)CCCC(C)CCCC(C)CC(=O)O
InChI: InChI=1S/C20H40O2/c1-16(2)9-6-10-17(3)11-7-12-18(4)13-8-14-19(5)15-20(21)22/h16-19H,6-15H2,1-5H3,(H,21,22)
描述信息
3D,7D,11D-Phytanic acid is an isomer of Phytanic acid, an unusual 20-carbon branched-chain fatty acid; Phytanic acid accumulates in blood and tissues of patients with Refsum disease (RD, an inborn error of lipid metabolism inherited as an autosomal recessive trait (OMIM 266500)), and is a reliable identifier of RD from a large number of other neurological disorders. Phytanic acid also accumulates in a number of other disorders with a very different clinical course: disorders of peroxisome biogenesis (Zellweger syndrome (OMIM 214100), neonatal adrenoleukodystrophy (OMIM 202370), infantile Refsum disease (OMIM 266510)) and rhizomelic chondrodysplasia punctata, type 1 (OMIM 215100). Phytanic acid is a 3-methyl fatty acid that cannot be beta-oxidized directly, and first undergoes an alpha-oxidation a reaction catalyzed by the enzyme phytanoyl-CoA hydroxylase, which is deficient in RD, the only true disorder of phytanic acid alpha-oxidation. (The Metabolic and Molecular Bases of Inherited Disease).
同义名列表
15 个代谢物同义名
3,7,11,15-Tetramethyl-[3R-(3R*,7R*,11R*)]-hexadecanoic acid; 3,7,11,15-Tetramethyl-[3R-(3R*,7R*,11R*)]-hexadecanoate; ((3R,7R,11R)-)3,7,11,15-Tetramethylhexadecanoic acid; (3R,7R,11R)-3,7,11,15-tetramethylhexadecanoic acid; ((3R,7R,11R)-)3,7,11,15-Tetramethylhexadecanoate; 3,7,11,15-Tetramethyl-D,D,D-hexadecanoic acid; 3,7,11,15-Tetramethyl-D,D,D-hexadecanoate; (3R,7R,11R)-1-Phytanoate; 3D,7D,11D-Phytanic acid; D,D,D-Phytanic acid; 3D,7D,11D-Phytanate; D,D,D-Phytanate; Phytanoic acid; PHYTANIC ACID; Phytanate
数据库引用编号
16 个数据库交叉引用编号
- ChEBI: CHEBI:172542
- ChEBI: CHEBI:16285
- KEGG: C01607
- PubChem: 10380830
- PubChem: 26840
- HMDB: HMDB0000417
- ChEMBL: CHEMBL4853893
- MeSH: Phytanic Acid
- chemspider: 8556273
- CAS: 14721-66-5
- CAS: 18654-64-3
- PMhub: MS000017292
- PubChem: 4760
- LipidMAPS: LMPR0104010004
- NIKKAJI: J14.320K
- KNApSAcK: 16285
分类词条
相关代谢途径
Reactome(5)
BioCyc(0)
PlantCyc(0)
代谢反应
0 个相关的代谢反应过程信息。
Reactome(0)
BioCyc(0)
WikiPathways(0)
Plant Reactome(0)
INOH(0)
PlantCyc(0)
COVID-19 Disease Map(0)
PathBank(0)
PharmGKB(0)
4 个相关的物种来源信息
- 202113 - Aplysina fistularis: 10.1007/BF02536024
- 289403 - Aplysina lacunosa: 10.1007/BF02536024
- 9606 - Homo sapiens: -
- 9606 - Homo sapiens: 10.1007/S11306-016-1051-4
在这里通过桑基图来展示出与当前的这个代谢物在我们的BioDeep知识库中具有相关联信息的其他代谢物。在这里进行关联的信息来源主要有：
- PubMed: 来源于PubMed文献库中的文献信息，我们通过自然语言数据挖掘得到的在同一篇文献中被同时提及的相关代谢物列表，这个列表按照代谢物同时出现的文献数量降序排序，取前10个代谢物作为相关研究中关联性很高的代谢物集合展示在桑基图中。
- NCBI Taxonomy: 通过文献数据挖掘，得到的代谢物物种来源信息关联。这个关联信息同样按照出现的次数降序排序，取前10个代谢物作为高关联度的代谢物集合展示在桑吉图上。
- Chemical Taxonomy: 在物质分类上处于同一个分类集合中的其他代谢物
- Chemical Reaction: 在化学反应过程中，存在为当前代谢物相关联的生化反应过程中的反应底物或者反应产物的关联代谢物信息。
点击图上的相关代谢物的名称，可以跳转到相关代谢物的信息页面。
文献列表
- Wentao Yang, Philipp Gutbrod, Katharina Gutbrod, Helga Peisker, Xiaoning Song, Anna-Lena Falz, Andreas J Meyer, Peter Dörmann. 2-Hydroxy-phytanoyl-CoA lyase (AtHPCL) is involved in phytol metabolism in Arabidopsis.
The Plant journal : for cell and molecular biology.
2022 03; 109(5):1290-1304. doi:
10.1111/tpj.15632. [PMID: 34902195] - Maaike Blankestijn, Vincent W Bloks, Dicky Struik, Nicolette Huijkman, Niels Kloosterhuis, Justina C Wolters, Ronald J A Wanders, Frédéric M Vaz, Markus Islinger, Folkert Kuipers, Bart van de Sluis, Albert K Groen, Henkjan J Verkade, Johan W Jonker. Mice with a deficiency in Peroxisomal Membrane Protein 4 (PXMP4) display mild changes in hepatic lipid metabolism.
Scientific reports.
2022 02; 12(1):2512. doi:
10.1038/s41598-022-06479-y. [PMID: 35169201] - Youssef Khalil, Sara Carrino, Fujun Lin, Anna Ferlin, Heena V Lad, Francesca Mazzacuva, Sara Falcone, Natalie Rivers, Gareth Banks, Danilo Concas, Carlos Aguilar, Andrew R Haynes, Andy Blease, Thomas Nicol, Raya Al-Shawi, Wendy Heywood, Paul Potter, Kevin Mills, Daniel P Gale, Peter T Clayton. Tissue Proteome of 2-Hydroxyacyl-CoA Lyase Deficient Mice Reveals Peroxisome Proliferation and Activation of ω-Oxidation.
International journal of molecular sciences.
2022 Jan; 23(2):. doi:
10.3390/ijms23020987. [PMID: 35055171] - Luz Díaz-Storani, Anaelle A Clary, Diego M Moreno, María Sol Ballari, Exequiel O J Porta, Andrea B J Bracca, Jonathan B Johnston, Guillermo R Labadie. Synthesis and interaction of terminal unsaturated chemical probes with Mycobacterium tuberculosis CYP124A1.
Bioorganic & medicinal chemistry.
2021 08; 44(?):116304. doi:
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The Journal of dairy research.
2020 Nov; 87(4):498-500. doi:
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Theriogenology.
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PloS one.
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2010 Sep; 9(?):98. doi:
10.1186/1476-511x-9-98. [PMID: 20828389] - Eleanor J Baldwin, F Brian Gibberd, Claire Harley, Margaret C Sidey, Michael D Feher, Anthony S Wierzbicki. The effectiveness of long-term dietary therapy in the treatment of adult Refsum disease.
Journal of neurology, neurosurgery, and psychiatry.
2010 Sep; 81(9):954-7. doi:
10.1136/jnnp.2008.161059. [PMID: 20547622] - Guilhian Leipnitz, Alexandre U Amaral, Angela Zanatta, Bianca Seminotti, Carolina G Fernandes, Lisiane A Knebel, Carmen R Vargas, Moacir Wajner. Neurochemical evidence that phytanic acid induces oxidative damage and reduces the antioxidant defenses in cerebellum and cerebral cortex of rats.
Life sciences.
2010 Aug; 87(9-10):275-80. doi:
10.1016/j.lfs.2010.06.015. [PMID: 20619275] - Hitoshi Kotani, Hiroki Tanabe, Hajime Mizukami, Makoto Makishima, Makoto Inoue. Identification of a naturally occurring rexinoid, honokiol, that activates the retinoid X receptor.
Journal of natural products.
2010 Aug; 73(8):1332-6. doi:
10.1021/np100120c. [PMID: 20695472] - Alison J Price, Naomi E Allen, Paul N Appleby, Francesca L Crowe, Mazda Jenab, Sabina Rinaldi, Nadia Slimani, Rudolf Kaaks, Sabine Rohrmann, Heiner Boeing, Tobias Pischon, Vassiliki Benetou, Androniki Naska, Antonia Trichopoulou, Domenico Palli, Sabina Sieri, Rosario Tumino, Paolo Vineis, H Bas Bueno-de-Mesquita, Ignacio Donate, Carlos A González, Maria-José Sánchez, Maria-Dolores Chirlaque, Eva Ardanaz, Nerea Larrañaga, Kay-Tee Khaw, Sheila Rodwell, Valentina Gallo, Dominique S Michaud, Elio Riboli, Timothy J Key. Plasma phytanic acid concentration and risk of prostate cancer: results from the European Prospective Investigation into Cancer and Nutrition.
The American journal of clinical nutrition.
2010 Jun; 91(6):1769-76. doi:
10.3945/ajcn.2009.28831. [PMID: 20427733] - Maiko Mitake, Hiroko Ogawa, Kazuo Uebaba, Yoshihiro Shidoji. Increase in plasma concentrations of geranylgeranoic Acid after turmeric tablet intake by healthy volunteers.
Journal of clinical biochemistry and nutrition.
2010 May; 46(3):252-8. doi:
10.3164/jcbn.09-109. [PMID: 20490321] - Manisha Sathe, Mariliza Derveni, Marjorie Allen, David C Cullen. Use of polystyrene-supported 2-isobutoxy-1-isobutoxycarbonyl-1,2-dihydroquinoline for the preparation of a hapten-protein conjugate for antibody development.
Bioorganic & medicinal chemistry letters.
2010 Mar; 20(5):1792-5. doi:
10.1016/j.bmcl.2009.12.078. [PMID: 20129781] - Lars I Hellgren. Phytanic acid--an overlooked bioactive fatty acid in dairy fat?.
Annals of the New York Academy of Sciences.
2010 Mar; 1190(?):42-9. doi:
10.1111/j.1749-6632.2009.05254.x. [PMID: 20388135] - Tsuyoshi Goto, Nobuyuki Takahashi, Shizuka Hirai, Teruo Kawada. Various Terpenoids Derived from Herbal and Dietary Plants Function as PPAR Modulators and Regulate Carbohydrate and Lipid Metabolism.
PPAR research.
2010; 2010(?):483958. doi:
10.1155/2010/483958. [PMID: 20613991] - Maryam Rakhshandehroo, Bianca Knoch, Michael Müller, Sander Kersten. Peroxisome proliferator-activated receptor alpha target genes.
PPAR research.
2010; 2010(?):. doi:
10.1155/2010/612089. [PMID: 20936127] - Jonathan B Johnston, Petrea M Kells, Larissa M Podust, Paul R Ortiz de Montellano. Biochemical and structural characterization of CYP124: a methyl-branched lipid omega-hydroxylase from Mycobacterium tuberculosis.
Proceedings of the National Academy of Sciences of the United States of America.
2009 Dec; 106(49):20687-92. doi:
10.1073/pnas.0907398106. [PMID: 19933331] - Cindy Krause, Hendrik Rosewich, Jutta Gärtner. Rational diagnostic strategy for Zellweger syndrome spectrum patients.
European journal of human genetics : EJHG.
2009 Jun; 17(6):741-8. doi:
10.1038/ejhg.2008.252. [PMID: 19142205] - S J Steinberg, A Snowden, N E Braverman, L Chen, P A Watkins, P T Clayton, K D R Setchell, J E Heubi, G V Raymond, A B Moser, H W Moser. A PEX10 defect in a patient with no detectable defect in peroxisome assembly or metabolism in cultured fibroblasts.
Journal of inherited metabolic disease.
2009 Feb; 32(1):109-19. doi:
10.1007/s10545-008-0969-8. [PMID: 19127411] - John T Mackie, Barbara P Atshaves, H Ross Payne, Avery L McIntosh, Friedhelm Schroeder, Ann B Kier. Phytol-induced hepatotoxicity in mice.
Toxicologic pathology.
2009 Feb; 37(2):201-8. doi:
10.1177/0192623308330789. [PMID: 19188468] - Tomoyuki Fukasawa, Koichiro Murashima, Tomoko Nemoto, Ichiro Matsumoto, Jinichiro Koga, Hidetoshi Kubota, Minoru Kanegae. Identification of marker genes for lipid-lowering effect of a short-chain fructooligosaccharide by DNA microarray analysis.
Journal of dietary supplements.
2009; 6(3):254-62. doi:
10.1080/19390210903070822. [PMID: 22435477] - Iria Nieto-Vazquez, Sonia Fernández-Veledo, Cristina de Alvaro, Margarita Lorenzo. Dual role of interleukin-6 in regulating insulin sensitivity in murine skeletal muscle.
Diabetes.
2008 Dec; 57(12):3211-21. doi:
10.2337/db07-1062. [PMID: 18796617] - Darren Magda, Philip Lecane, Julia Prescott, Patricia Thiemann, Xuan Ma, Patricia K Dranchak, Donna M Toleno, Krishna Ramaswamy, Kimberly D Siegmund, Joseph G Hacia. mtDNA depletion confers specific gene expression profiles in human cells grown in culture and in xenograft.
BMC genomics.
2008 Nov; 9(?):521. doi:
10.1186/1471-2164-9-521. [PMID: 18980691] - Marina Moraitou, Evangelia Dimitriou, Dimitrios Zafeiriou, Constantina Reppa, Theodoros Marinakis, Jasmin Sarafidou, Helen Michelakakis. Plasmalogen levels in Gaucher disease.
Blood cells, molecules & diseases.
2008 Sep; 41(2):196-9. doi:
10.1016/j.bcmd.2008.03.007. [PMID: 18501647] - Osama Y Al-Dirbashi, Tomofumi Santa, Mohamed S Rashed, Zuhair Al-Hassnan, Nobuyuki Shimozawa, Aziza Chedrawi, Minnie Jacob, Manhal Al-Mokhadab. Rapid UPLC-MS/MS method for routine analysis of plasma pristanic, phytanic, and very long chain fatty acid markers of peroxisomal disorders.
Journal of lipid research.
2008 Aug; 49(8):1855-62. doi:
10.1194/jlr.d800019-jlr200. [PMID: 18441019] - Rosalba Carrozzo, Carlo Bellini, Simona Lucioli, Federica Deodato, Denise Cassandrini, Michela Cassanello, Ubaldo Caruso, Cristiano Rizzo, Teresa Rizza, Matteo L Napolitano, Ronald J A Wanders, Cornelis Jakobs, Claudio Bruno, Filippo M Santorelli, Carlo Dionisi-Vici, Eugenio Bonioli. Peroxisomal acyl-CoA-oxidase deficiency: two new cases.
American journal of medical genetics. Part A.
2008 Jul; 146A(13):1676-81. doi:
10.1002/ajmg.a.32298. [PMID: 18536048] - C H Raine, M F Kurukulasuriya, Y Bajaj, D R Strachan. Cochlear implantation in Refsum's disease.
Cochlear implants international.
2008 Jun; 9(2):97-102. doi:
10.1179/cim.2008.9.2.97. [PMID: 18698664] - Osman A B S M Gani. Are fish oil omega-3 long-chain fatty acids and their derivatives peroxisome proliferator-activated receptor agonists?.
Cardiovascular diabetology.
2008 Mar; 7(?):6. doi:
10.1186/1475-2840-7-6. [PMID: 18355413] - Josef Finsterer, Günther Regelsberger, Till Voigtländer. Refsum disease due to the splice-site mutation c.135-2A>G before exon 3 of the PHYH gene, diagnosed eight years after detection of retinitis pigmentosa.
Journal of the neurological sciences.
2008 Mar; 266(1-2):182-6. doi:
10.1016/j.jns.2007.09.005. [PMID: 17905308] - Naomi E Allen, Philip B Grace, Annette Ginn, Ruth C Travis, Andrew W Roddam, Paul N Appleby, Timothy Key. Phytanic acid: measurement of plasma concentrations by gas-liquid chromatography-mass spectrometry analysis and associations with diet and other plasma fatty acids.
The British journal of nutrition.
2008 Mar; 99(3):653-9. doi:
10.1017/s000711450782407x. [PMID: 17868488] - Davide Genini, Giuseppina M Carbone, Carlo V Catapano. Multiple Interactions between Peroxisome Proliferators-Activated Receptors and the Ubiquitin-Proteasome System and Implications for Cancer Pathogenesis.
PPAR research.
2008; 2008(?):195065. doi:
10.1155/2008/195065. [PMID: 18551186] - Bing Song Zheng, Elin Rönnberg, Lenita Viitanen, Tiina A Salminen, Krister Lundgren, Thomas Moritz, Johan Edqvist. Arabidopsis sterol carrier protein-2 is required for normal development of seeds and seedlings.
Journal of experimental botany.
2008; 59(12):3485-99. doi:
10.1093/jxb/ern201. [PMID: 18687588] - Maria Stacewicz-Sapuntzakis, Gayatri Borthakur, James L Burns, Phyllis E Bowen. Correlations of dietary patterns with prostate health.
Molecular nutrition & food research.
2008 Jan; 52(1):114-30. doi:
10.1002/mnfr.200600296. [PMID: 18080240] - J C Komen, F Distelmaier, W J H Koopman, R J A Wanders, J Smeitink, P H M G Willems. Phytanic acid impairs mitochondrial respiration through protonophoric action.
Cellular and molecular life sciences : CMLS.
2007 Dec; 64(24):3271-81. doi:
10.1007/s00018-007-7357-7. [PMID: 17968498] - Barbara P Atshaves, Avery L McIntosh, Danilo Landrock, H Ross Payne, John T Mackie, Nobuyo Maeda, Judith Ball, Friedhelm Schroeder, Ann B Kier. Effect of SCP-x gene ablation on branched-chain fatty acid metabolism.
American journal of physiology. Gastrointestinal and liver physiology.
2007 Mar; 292(3):G939-51. doi:
10.1152/ajpgi.00308.2006. [PMID: 17068117] - J Gloerich, D M van den Brink, J P N Ruiter, N van Vlies, F M Vaz, R J A Wanders, S Ferdinandusse. Metabolism of phytol to phytanic acid in the mouse, and the role of PPARalpha in its regulation.
Journal of lipid research.
2007 Jan; 48(1):77-85. doi:
10.1194/jlr.m600050-jlr200. [PMID: 17015885] - Francesc Villarroya, Roser Iglesias, Marta Giralt. PPARs in the Control of Uncoupling Proteins Gene Expression.
PPAR research.
2007; 2007(?):74364. doi:
10.1155/2007/74364. [PMID: 17389766] - Xiao-Han Tang, Moo-Jin Suh, Rong Li, Lorraine J Gudas. Cell proliferation inhibition and alterations in retinol esterification induced by phytanic acid and docosahexaenoic acid.
Journal of lipid research.
2007 Jan; 48(1):165-76. doi:
10.1194/jlr.m600419-jlr200. [PMID: 17068359] - Christophe Verny, Adriana Prundean, Guillaume Nicolas, Vivien Pautot, Dominique Maugin, Thierry Levade, Dominique Bonneau, Frederic Dubas. Refsum's disease may mimic familial Guillain Barre syndrome.
Neuromuscular disorders : NMD.
2006 Nov; 16(11):805-8. doi:
10.1016/j.nmd.2006.07.001. [PMID: 16934464] - M R F Lee, P L Connelly, J K S Tweed, R J Dewhurst, R J Merry, N D Scollan. Effects of high-sugar ryegrass silage and mixtures with red clover silage on ruminant digestion. 2. Lipids.
Journal of animal science.
2006 Nov; 84(11):3061-70. doi:
10.2527/jas.2005-736. [PMID: 17032800] - J C Komen, R J A Wanders. Identification of the cytochrome P450 enzymes responsible for the omega-hydroxylation of phytanic acid.
FEBS letters.
2006 Jul; 580(16):3794-8. doi:
10.1016/j.febslet.2006.05.069. [PMID: 16782090] - Peter Schönfeld, Stefan Kahlert, Georg Reiser. A study of the cytotoxicity of branched-chain phytanic acid with mitochondria and rat brain astrocytes.
Experimental gerontology.
2006 Jul; 41(7):688-96. doi:
10.1016/j.exger.2006.02.013. [PMID: 16616447] - Nathalie Lepage, Dailin Li, Peter A Kavsak, Fiona Bamforth, John Callahan, Kent Dooley, Murray Potter. Incomplete pediatric reference intervals for the management of patients with inborn errors of metabolism.
Clinical biochemistry.
2006 Jun; 39(6):595-9. doi:
10.1016/j.clinbiochem.2006.02.011. [PMID: 16595129] - H Rosewich, H R Waterham, R J A Wanders, S Ferdinandusse, M Henneke, D Hunneman, J Gärtner. Pitfall in metabolic screening in a patient with fatal peroxisomal beta-oxidation defect.
Neuropediatrics.
2006 Apr; 37(2):95-8. doi:
10.1055/s-2006-923943. [PMID: 16773508] - Toru Hashimoto, Naoto Shimizu, Toshinori Kimura, Yoko Takahashi, Takashi Ide. Polyunsaturated fats attenuate the dietary phytol-induced increase in hepatic fatty acid oxidation in mice.
The Journal of nutrition.
2006 Apr; 136(4):882-6. doi:
10.1093/jn/136.4.882. [PMID: 16549445] - Georg Reiser, Peter Schönfeld, Stefan Kahlert. Mechanism of toxicity of the branched-chain fatty acid phytanic acid, a marker of Refsum disease, in astrocytes involves mitochondrial impairment.
International journal of developmental neuroscience : the official journal of the International Society for Developmental Neuroscience.
2006 Apr; 24(2-3):113-22. doi:
10.1016/j.ijdevneu.2005.11.002. [PMID: 16386870] - M Casteels. [alpha-Oxidation of 3-methyl-branched fatty acids: unraveling of a pathway].
Verhandelingen - Koninklijke Academie voor Geneeskunde van Belgie.
2006; 68(3):199-221; discussion 221. doi:
. [PMID: 16796018] - Tsuyoshi Goto, Nobuyuki Takahashi, Sota Kato, Kahori Egawa, Shogo Ebisu, Tatsuya Moriyama, Tohru Fushiki, Teruo Kawada. Phytol directly activates peroxisome proliferator-activated receptor alpha (PPARalpha) and regulates gene expression involved in lipid metabolism in PPARalpha-expressing HepG2 hepatocytes.
Biochemical and biophysical research communications.
2005 Nov; 337(2):440-5. doi:
10.1016/j.bbrc.2005.09.077. [PMID: 16202384] - Patrick C Walsh. Serum levels of phytanic acid are associated with prostate cancer risk.
The Journal of urology.
2005 Nov; 174(5):1824. doi:
NULL. [PMID: 16217297] - K Rüther. [Adult Refsum disease. A retinal dystrophy with therapeutic options].
Der Ophthalmologe : Zeitschrift der Deutschen Ophthalmologischen Gesellschaft.
2005 Aug; 102(8):772-7. doi:
10.1007/s00347-005-1239-x. [PMID: 15990985] - Jianfeng Xu, Todd Thornburg, Aubrey R Turner, Mara Vitolins, Doug Case, John Shadle, Lisa Hinson, Jielin Sun, Wennuan Liu, Baoli Chang, Tamara S Adams, S Lilly Zheng, Frank M Torti. Serum levels of phytanic acid are associated with prostate cancer risk.
The Prostate.
2005 May; 63(3):209-14. doi:
10.1002/pros.20233. [PMID: 15712232] - Veerle Foulon, Mieke Sniekers, Els Huysmans, Stanny Asselberghs, Vincent Mahieu, Guy P Mannaerts, Paul P Van Veldhoven, Minne Casteels. Breakdown of 2-hydroxylated straight chain fatty acids via peroxisomal 2-hydroxyphytanoyl-CoA lyase: a revised pathway for the alpha-oxidation of straight chain fatty acids.
The Journal of biological chemistry.
2005 Mar; 280(11):9802-12. doi:
10.1074/jbc.m413362200. [PMID: 15644336]