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MetaCyc Pathway: octane oxidation
Inferred from experiment

Pathway diagram: octane 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/AssimilationDegradation/Utilization/Assimilation - Other

Some taxa known to possess this pathway include : Pseudomonas oleovorans

Expected Taxonomic Range: Bacteria , Fungi

Studies have shown that the capacity to use hydrocarbons as sole carbon and energy source is very common, and not restricted to any particular group of microorganisms. Examples were found in a wide range of prokaryotic and eukaryotic genera including Gram-negative and Gram-positive bacteria, yeasts, fungi, and even some achlorophyllous algae [vanBeilen94]. One of these organisms is the Gram negative bacterium Pseudomonas oleovorans, isolated from machine shop cutting oil [Lee41], which can grow on intermediate chain length n-alkanes (C6 to C12). This pathway describes the oxidation of n-octane by this organism.

The key enzyme in this pathway is the alkane hydroxylase system, which is encoded by the OCT plasmid [Chakrabarty73]. The alkane hydroxylase system system introduces molecular oxygen in the terminal carbon atom of the hydrocarbons at the expense of NADH [Ueda72] to yield primary alcohols [Chen95]. It is composed of three components - a alkane 1-monooxygenase, a rubredoxin 2, and a rubredoxin-NAD(+) reductase. The NADH-dependent rubredoxin-NAD(+) reductase transfers the electrons from NADH, via the electron carrier rubredoxin 2, to the monooxygenase, which reduces the other oxygen atom.

The product of the hydroxylase system, 1-octanol, is then further catabolized by an octanol dehydrogenase, an aldehyde dehydrogenase and an medium-chain acyl-CoA synthetase. The final product, octanoyl-CoA, enters the β-oxidation-cycle, and can be utilized as a carbon and energy source [vanBeilen92, vanBeilen94].

Unification Links: Eawag-BBD-Pathways:oct

Created 15-Aug-2000 by Pellegrini-Toole A, Marine Biological Laboratory
Revised 24-Oct-2007 by Caspi R, SRI International


Baptist63: Baptist, J. N., Gholson, R. K., Coon, M. J. (1963). "Hydrocarbon oxidation by a bacterial enzyme system. I. Products of octane oxidation." Biochim. Biophys. Acta 69:40-47.

Chakrabarty73: Chakrabarty AM, Chou G, Gunsalus IC (1973). "Genetic regulation of octane dissimilation plasmid in Pseudomonas." Proc Natl Acad Sci U S A 70(4);1137-40. PMID: 4515610

Chen95: Chen Q, Janssen DB, Witholt B (1995). "Growth on octane alters the membrane lipid fatty acids of Pseudomonas oleovorans due to the induction of alkB and synthesis of octanol." J Bacteriol 177(23);6894-901. PMID: 7592483

Lee41: Lee M, Chandler AC (1941). "A Study of the Nature, Growth and Control of Bacteria in Cutting Compounds." J Bacteriol 41(3);373-86. PMID: 16560407

Ueda72: Ueda T, Coon MJ (1972). "Enzymatic oxidation. VII. Reduced diphosphopyridine nucleotide-rubredoxin reductase: properties and function as an electron carrier in hydroxylation." J Biol Chem 1972;247(16);5010-6. PMID: 4403503

vanBeilen92: van Beilen JB, Eggink G, Enequist H, Bos R, Witholt B (1992). "DNA sequence determination and functional characterization of the OCT-plasmid-encoded alkJKL genes of Pseudomonas oleovorans." Mol Microbiol 1992;6(21);3121-36. PMID: 1453953

vanBeilen94: van Beilen JB, Wubbolts MG, Witholt B (1994). "Genetics of alkane oxidation by Pseudomonas oleovorans." Biodegradation 1994;5(3-4);161-74. PMID: 7532480

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

Benson79: Benson S, Oppici M, Shapiro J, Fennewald M (1979). "Regulation of membrane peptides by the Pseudomonas plasmid alk regulon." J Bacteriol 140(3);754-62. PMID: 533768

Brady79: Brady FO, Bunger PC (1979). "The effect of adrenalectomy on zinc thionein levels in rat liver." Biochem Biophys Res Commun 1979;91(3);911-8. PMID: 526290

Eggink87: Eggink G, Lageveen RG, Altenburg B, Witholt B (1987). "Controlled and functional expression of the Pseudomonas oleovorans alkane utilizing system in Pseudomonas putida and Escherichia coli." J Biol Chem 262(36);17712-8. PMID: 2826430

Eggink90: Eggink G, Engel H, Vriend G, Terpstra P, Witholt B (1990). "Rubredoxin reductase of Pseudomonas oleovorans. Structural relationship to other flavoprotein oxidoreductases based on one NAD and two FAD fingerprints." J Mol Biol 212(1);135-42. PMID: 2319593

Guedon01: Guedon E, Petitdemange H (2001). "Identification of the gene encoding NADH-rubredoxin oxidoreductase in Clostridium acetobutylicum." Biochem Biophys Res Commun 285(2);496-502. PMID: 11444870

Jones86: Jones DT, Woods DR (1986). "Acetone-butanol fermentation revisited." Microbiol Rev 1986;50(4);484-524. PMID: 3540574

Katsuyama10: Katsuyama Y, Ohnishi Y, Horinouchi S (2010). "Production of dehydrogingerdione derivatives in Escherichia coli by exploiting a curcuminoid synthase from Oryza sativa and a β-oxidation pathway from Saccharomyces cerevisiae." Chembiochem 11(14);2034-41. PMID: 20836122

Kok89: Kok M, Oldenhuis R, van der Linden MP, Raatjes P, Kingma J, van Lelyveld PH, Witholt B (1989). "The Pseudomonas oleovorans alkane hydroxylase gene. Sequence and expression." J Biol Chem 264(10);5435-41. PMID: 2647718

Kok89a: Kok M, Oldenhuis R, van der Linden MP, Meulenberg CH, Kingma J, Witholt B (1989). "The Pseudomonas oleovorans alkBAC operon encodes two structurally related rubredoxins and an aldehyde dehydrogenase." J Biol Chem 264(10);5442-51. PMID: 2647719

Kurys89: Kurys G, Ambroziak W, Pietruszko R (1989). "Human aldehyde dehydrogenase. Purification and characterization of a third isozyme with low Km for gamma-aminobutyraldehyde." J Biol Chem 264(8);4715-21. PMID: 2925663

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

Lloyd07: Lloyd MD, Boardman KD, Smith A, van den Brink DM, Wanders RJ, Threadgill MD (2007). "Characterisation of recombinant human fatty aldehyde dehydrogenase: implications for Sjogren-Larsson syndrome." J Enzyme Inhib Med Chem 22(5);584-90. PMID: 18035827

Marczak84: Marczak R, Ballongue J, Petitdemange H, Gay R "Regulation of the biosynthesis of NADH-rubredoxin oxidoreductasein Clostridium acetobutylicum." Current Microbiology 10:165-168 (1984).

Marczak85: Marczak R, Ballongue J, Petitdemange H, Gay R (1985). "Differential levels of ferredoxin and rubredoxin in Clostridium acetobutylicum." Biochimie 1985;67(2);241-8. PMID: 4005308

Peterson68: Peterson JA, Coon MJ (1968). "Enzymatic omega-oxidation. 3. Purification and properties of rubredoxin, a component of the omega-hydroxylation system of Pseudomonas oleovorans." J Biol Chem 243(2);329-34. PMID: 4295540

Petitdemange79: Petitdemange H, Marczak R, Blusson H, Gay R (1979). "Isolation and properties of reduced nicotinamide adenine dinucleotiderubredoxin oxidoreductase of Clostridium acetobutylicum." Biochem Biophys Res Commun 1979;91(4);1258-65. PMID: 526302

Petitdemange81: Petitdemange H, Blusson H, Gay R (1981). "Detection of NAD(P)H--rubredoxin oxidoreductases in Clostridia." Anal Biochem 1981;116(2);564-70. PMID: 6274224

Rougraff89: Rougraff PM, Zhang B, Kuntz MJ, Harris RA, Crabb DW (1989). "Cloning and sequence analysis of a cDNA for 3-hydroxyisobutyrate dehydrogenase. Evidence for its evolutionary relationship to other pyridine nucleotide-dependent dehydrogenases." J Biol Chem 264(10);5899-903. PMID: 2647728

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

Ruettinger74: Ruettinger RT, Olson ST, Boyer RF, Coon MJ (1974). "Identification of the omega-hydroxylase of Pseudomonas oleovorans as a nonheme iron protein requiring phospholipid for catalytic activity." Biochem Biophys Res Commun 1974;57(4);1011-7. PMID: 4830742

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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
Page generated by Pathway Tools version 19.5 (software by SRI International) on Sun May 1, 2016, biocyc14.