MetaCyc Pathway: ethylene biosynthesis II (microbes)

Enzyme View:

Pathway diagram: ethylene biosynthesis II (microbes)

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: Biosynthesis Hormones Biosynthesis Plant Hormones Biosynthesis Ethylene Biosynthesis

Some taxa known to possess this pathway include ? : Penicillium digitatum , Pseudomonas amygdali pv. sesami , Pseudomonas savastanoi pv. glycinea , Pseudomonas savastanoi pv. phaseolicola

Expected Taxonomic Range: Bacteria , Fungi

General Background

Ethylene is known in plants, fungi and bacteria. In plants, ethylene is an important hormone that regulates plant growth and development. It is well-known as a fruit-ripening hormone and is biologically active in trace amounts. Ethylene also plays a general role as a growth inhibitor in promoting leaf and flower senescence and abscission.

All plants produce ethylene from L-methionine as described in the pathway ethylene biosynthesis I (plants). In addition, two alternative ethylene biosynthetic pathways have been reported from microorganisms. Most microorganisms produce only trace amounts of ethylene via the 2-oxo-4-methylthiobutanoate (KMBA) pathway [Nagahama92] (see ethylene biosynthesis III (microbes)). In that pathway ethylene is produced non-enzymatically by hydroxyl radicals that are produced from molecular oxygen by an NADH:Fe(III)EDTA oxidoreductase [Ince86, Fukuda89, Ogawa90]. The second microbial pathway, which is described here, is found mostly in members of the Pseudomonas syringae group. In this pathway ethylene is formed enzymatically from 2-oxoglutarate.

Being the simplest unsaturated organic molecule, ethylene is the building block for synthetic polymers including plastics such as polyethylene. Large amounts of ethylene are currently produced in a chemical process from fossil fuels. Ethylene has the highest annual global production of all synthetic organic molecules.

About This Pathway

A novel ethylene-forming enzyme that forms ethylene from 2-ketoglutarate was purified in 1989 from Penicillium digitatum IFO 9372, the green mold of citrus fruit that is known to produce large quantities of ethylene [Fukuda89a]. The substrate and cofactor specificities of the enzyme, which was named simply "ethylene-forming enzyme", were highly specific for 2-ketoglutarate and L-arginine, respectively.

An enzyme with a very similar activity, although a different amino acid sequence, has been described from the bacterium Pseudomonas savastanoi pv. phaseolicola [Goto87, Nagahama91a, Nagahama91, Fukuda92a]. The enzyme is plasmid-encoded, and has been eventually detected in many strains of Pseudomonas syringae [Fukuda92, Nagahama94]. The enzyme catalyzes a very complex reaction, or more accurately, two simultaneous reactions followed by yet a third reaction. In the main reaction 2-oxoglutarate is dioxygenated to form one molecule of ethylene and three molecules of carbon dioxide. In a second reaction both 2-oxoglutarate and L-arginine are mono-oxygenated simultaneously to yield succinate plus CO2 and Nω-hydroxy-L-arginine, respectively. The latter is further transformed in a third reaction to guanidinium and (S)-1-pyrroline-5-carboxylate. The overall reaction can be described as

3 2-oxoglutarate + L-arginine + 3 oxygen + 3 H+ → 2 ethylene + 7 CO2 + succinate + guanidinium + (S)-1-pyrroline-5-carboxylate + 3 H2O

The main product of the enzyme is ethylene. The purpose of the in vivo production of succinate is not clear. It has been suggested that this reaction supresses the ethylene-forming reaction via the decomposition of L-arginine.

One of the final products, (S)-1-pyrroline-5-carboxylate, can be converted to L-glutamate by EC, 1-pyrroline-5-carboxylate dehydrogenase. The glutamate that is formed can be recycled back to L-arginine via the acetyl cycle, thus feeding back into the succinate-forming reaction of the ethylene-forming enzyme.

The efe gene, which encodes the ethylene-forming enzyme, has been cloned and expressed successfully in many organisms including Escherichia coli BL21 [Dong07], Saccharomyces cerevisiae [Pirkov08], Trichoderma viride [Tao08a], Synechococcus elongatus PCC 7942 [Takahama03] and in Pseudomonas putida KT2440 [Wang10a].

The organism Penicillium digitatum is unique in that it is able to produce ethylene via both this pathway and ethylene biosynthesis III (microbes), depending on the culture conditions [Chalutz77].

Variants: ethylene biosynthesis I (plants) , ethylene biosynthesis III (microbes) , ethylene biosynthesis V (engineered)

Created 05-Aug-2011 by Caspi R , SRI International


Chalutz77: Chalutz E, Lieberman M (1977). "Methionine-induced Ethylene Production by Penicillium digitatum." Plant Physiol 60(3);402-6. PMID: 16660102

Dong07: Dong, H. J., Wu, L.X., Chen, S.F. (2007). "Cloning and expressing of ethylene-forming enzyme gene from Pseudomonas syringae pv. glycinea ICMP2189." J. Agric. Biotechnol. 15:698-701.

Fukuda89: Fukuda H, Takahashi M, Fujii T, Tazaki M, Ogawa T (1989). "An NADH:Fe(III)EDTA oxidoreductase from Cryptococcus albidus: an enzyme involved in ethylene production in vivo?." FEMS Microbiol Lett 51(1);107-11. PMID: 2792734

Fukuda89a: Fukuda, H, Kitajima, H, Fujii, T, Tazaki, M, Ogawa, T (1989). "Purification and some properties of a novel ethylene-forming enzyme produced by Penicillium digitatum." FEMS Microbiology Letters 59:1-6.

Fukuda92: Fukuda H, Ogawa T, Ishihara K, Fujii T, Nagahama K, Omata T, Inoue Y, Tanase S, Morino Y (1992). "Molecular cloning in Escherichia coli, expression, and nucleotide sequence of the gene for the ethylene-forming enzyme of Pseudomonas syringae pv. phaseolicola PK2." Biochem Biophys Res Commun 188(2);826-32. PMID: 1445325

Fukuda92a: Fukuda H, Ogawa T, Tazaki M, Nagahama K, Fujii T, Tanase S, Morino Y (1992). "Two reactions are simultaneously catalyzed by a single enzyme: the arginine-dependent simultaneous formation of two products, ethylene and succinate, from 2-oxoglutarate by an enzyme from Pseudomonas syringae." Biochem Biophys Res Commun 188(2);483-9. PMID: 1445291

Goto87: Goto, M., Hyodo, H. (1987). "Ethylene production by cell-free extract of the kudzu strain of pseudomonas syringae pv.phaseolicola ." Plant and Cell Physiology 28(3):405-414.

Ince86: Ince JE, Knowles CJ (1986). "Ethylene formation by cell-free extracts of Escherichia coli." Arch Microbiol 146(2);151-8. PMID: 3541827

Nagahama91: Nagahama, K., Ogawa, T., Fujii, T., Tazaki, M., Tanase, S., Morino, Y., Fukuda, H. (1991). "Purification and properties of an ethylene-forming enzyme from Pseudomonas syringae pv. Phaseolicola PK2." Journal of General Microbiology 137(10):2281-2286. PMID: 1770346

Nagahama91a: Nagahama, K., Ogawa, T., Fujii, T., Tazaki, M., Goto, M., Fukuda, H. (1991). "L-Arginine is essential for the formation in vitro of ethylene by an extract of Pseudomonas syringae." Journal of General Microbiology 137(7):1641-1646.

Nagahama92: Nagahama, K., Ogawa, T., Fujii, T., Fukuda, H. (1992). "Classification of ethylene-producing bacteria in terms of biosynthetic pathways to ethylene." Journal of Fermentation and Bioengineering 73(1):1-5.

Nagahama94: Nagahama K, Yoshino K, Matsuoka M, Sato M, Tanase S, Ogawa T, Fukuda H (1994). "Ethylene production by strains of the plant-pathogenic bacterium Pseudomonas syringae depends upon the presence of indigenous plasmids carrying homologous genes for the ethylene-forming enzyme." Microbiology 140 ( Pt 9);2309-13. PMID: 7952184

Ogawa90: Ogawa, T., Takahashi, M., Fujii, T., Tazaki, M., Fukuda, H. (1990). "The Role of NADH:Fe(III)EDTA Oxidoreductase in Ethylene Formation from 2-Keto-4-Methylthiobutyrate." Journal of Fermentation and Bioengineering 69(5):287-291.

Pirkov08: Pirkov I, Albers E, Norbeck J, Larsson C (2008). "Ethylene production by metabolic engineering of the yeast Saccharomyces cerevisiae." Metab Eng 10(5);276-80. PMID: 18640286

Takahama03: Takahama K, Matsuoka M, Nagahama K, Ogawa T (2003). "Construction and analysis of a recombinant cyanobacterium expressing a chromosomally inserted gene for an ethylene-forming enzyme at the psbAI locus." J Biosci Bioeng 95(3);302-5. PMID: 16233410

Tao08a: Tao L, Dong HJ, Chen X, Chen SF, Wang TH (2008). "Expression of ethylene-forming enzyme (EFE) of Pseudomonas syringae pv. glycinea in Trichoderma viride." Appl Microbiol Biotechnol 80(4);573-8. PMID: 18575855

Wang10a: Wang JP, Wu LX, Xu F, Lv J, Jin HJ, Chen SF (2010). "Metabolic engineering for ethylene production by inserting the ethylene-forming enzyme gene (efe) at the 16S rDNA sites of Pseudomonas putida KT2440." Bioresour Technol 101(16);6404-9. PMID: 20399645

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

Brown92: Brown ED, Wood JM (1992). "Redesigned purification yields a fully functional PutA protein dimer from Escherichia coli." J Biol Chem 1992;267(18);13086-92. PMID: 1618807

BSUB93: "Bacillus subtilis and Other Gram-Positive Bacteria: Biochemistry, Physiology, and Molecular Genetics." (1993). Editors: Sonenshein, A.L., Hoch, J.A., Losick, R. American Society For Microbiology, Washington, DC.

Deuschle04: Deuschle K, Funck D, Forlani G, Stransky H, Biehl A, Leister D, van der Graaff E, Kunze R, Frommer WB (2004). "The role of [Delta]1-pyrroline-5-carboxylate dehydrogenase in proline degradation." Plant Cell 16(12);3413-25. PMID: 15548746

Forlani97: Forlani, Giuseppe, Scainelli, Damiano, Nielsen, Erik (1997). "Delta1-pyrroline-5-carboxylate dehydrogenase from cultured cells of potato." Plant Physiology 113:1413-1418. PMID: 12223682

ForteMcRobbie86: Forte-McRobbie CM, Pietruszko R (1986). "Purification and characterization of human liver "high Km" aldehyde dehydrogenase and its identification as glutamic gamma-semialdehyde dehydrogenase." J Biol Chem 261(5);2154-63. PMID: 3944130

ForteMcRobbie89: Forte-McRobbie C, Pietruszko R (1989). "Human glutamic-gamma-semialdehyde dehydrogenase. Kinetic mechanism." Biochem J 261(3);935-43. PMID: 2803253

Gardan95: Gardan R, Rapoport G, Debarbouille M (1995). "Expression of the rocDEF operon involved in arginine catabolism in Bacillus subtilis." J Mol Biol 1995;249(5);843-56. PMID: 7540694

Gardan97: Gardan R, Rapoport G, Debarbouille M (1997). "Role of the transcriptional activator RocR in the arginine-degradation pathway of Bacillus subtilis." Mol Microbiol 1997;24(4);825-37. PMID: 9194709

Hu96: Hu CA, Lin WW, Valle D (1996). "Cloning, characterization, and expression of cDNAs encoding human delta 1-pyrroline-5-carboxylate dehydrogenase." J Biol Chem 271(16);9795-800. PMID: 8621661

Ju04: Ju J, Ozanick SG, Shen B, Thomas MG (2004). "Conversion of (2S)-arginine to (2S,3R)-capreomycidine by VioC and VioD from the viomycin biosynthetic pathway of Streptomyces sp. strain ATCC11861." Chembiochem 5(9);1281-5. PMID: 15368582

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

Srivastava12: Srivastava D, Singh RK, Moxley MA, Henzl MT, Becker DF, Tanner JJ (2012). "The three-dimensional structural basis of type II hyperprolinemia." J Mol Biol 420(3);176-89. PMID: 22516612

Vogel52: Vogel HJ, Davis BD (1952). "Glutamic γ-Semialdehyde and Δ1-Pyrroline-5-carboxylic Acid, Intermediates in the Biosynthesis of Proline." J Am Chem Soc 74:109-112.

Williams75: Williams I, Frank L "Improved chemical synthesis and enzymatic assay of a delta-pyrroline-5-carboxylic acid." Analytical Biochemistry 1975;64:85-97.

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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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