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MetaCyc Engineered Pathway: long chain fatty acid ester synthesis for microdiesel production

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: Generation of Precursor Metabolites and Energy

Note: This is an engineered pathway. It does not occur naturally in any known organism, and has been constructed in a living cell by metabolic engineering.

The enzymes catalyzing the steps of this pathway have been assembled from the following organisms ? : Acinetobacter sp. ADP1 Inferred from experiment [Kalscheuer06], Escherichia coli K-12 substr. MG1655 , Zymomonas mobilis Inferred from experiment [Kalscheuer06]

Summary:
Background

The synthesis of fatty acid methyl esters (FAMEs) and fatty acid ethyl esters (FAEEs) by transesterification of long chain fatty acids from plant oil triacylglycerols (TAGs) with methanol and ethanol, respectively, produces biodiesel that can be used as a petroleum-based diesel substitute [Kalscheuer06]. The use of biodiesel has many positive ecological aspects, however, there are numerous limitations and drawbacks to its production on a technical scale. These include:

1) Production depending on the availability of sufficient vegetable oil feedstock.

2) Vegetable oils used contain TAGs which cannot be used directly and have to be transesterified, this is cost intensive and energy consuming.

3) The production of FAMEs requires methanol which is currently produced from natural gas, thus FAME-based biodiesel is not truly a renewable product.

About this Pathway

This pathway for the biosynthesis of FAEEs was metabolically engineered in Escherichia coli [Kalscheuer06]. The Zymomonas mobilis pyruvate decarboxylase and alcohol dehydrogenase II enzymes were cloned to aerobically generate ethanol, and wax ester synthase/acyl-CoA diacylglycerol acyltransferase bifunctional enzyme (WS/DGAT) from Acinetobacter sp. ADP1 was cloned to transesterify the acyl moieties of fatty acyl-CoA thioesters in Escherichia coli [Kalscheuer06]. Cells were cultivated aerobically with glucose and oleic acid.

Credits:
Created 24-Aug-2011 by Weerasinghe D , SRI International
Revised 04-Apr-2012 by Caspi R , SRI International


References

Kalscheuer06: Kalscheuer R, Stolting T, Steinbuchel A (2006). "Microdiesel: Escherichia coli engineered for fuel production." Microbiology 152(Pt 9);2529-36. PMID: 16946248

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

Catalanotti12: Catalanotti C, Dubini A, Subramanian V, Yang W, Magneschi L, Mus F, Seibert M, Posewitz MC, Grossman AR (2012). "Altered fermentative metabolism in Chlamydomonas reinhardtii mutants lacking pyruvate formate lyase and both pyruvate formate lyase and alcohol dehydrogenase." Plant Cell 24(2);692-707. PMID: 22353371

Chae11: Chae, Lee (2011). "The functional annotation of protein sequences was performed by the in-house Ensemble Enzyme Prediction Pipeline (E2P2, version 1.0). E2P2 systematically integrates results from three molecular function annotation algorithms using an ensemble classification scheme. For a given genome, all protein sequences are submitted as individual queries against the base-level annotation methods. The individual methods rely on homology transfer to annotate protein sequences, using single sequence (BLAST, E-value cutoff <= 1e-30, subset of SwissProt 15.3) and multiple sequence (Priam, November 2010; CatFam, version 2.0, 1% FDR profile library) models of enzymatic functions. The base-level predictions are then integrated into a final set of annotations using an average weighted integration algorithm, where the weight of each prediction from each individual method was determined via a 0.632 bootstrap process over 1000 rounds of testing. The training and testing data for E2P2 and the BLAST reference database were drawn from protein sequences with experimental support of existence, compiled from SwissProt release 15.3."

Conway87: Conway T, Sewell GW, Osman YA, Ingram LO (1987). "Cloning and sequencing of the alcohol dehydrogenase II gene from Zymomonas mobilis." J Bacteriol 169(6);2591-7. PMID: 3584063

Dennis91: Dennis MW, Kolattukudy PE (1991). "Alkane biosynthesis by decarbonylation of aldehyde catalyzed by a microsomal preparation from Botryococcus braunii." Arch Biochem Biophys 287(2);268-75. PMID: 1898004

Dickinson00: Dickinson JR, Harrison SJ, Dickinson JA, Hewlins MJ (2000). "An investigation of the metabolism of isoleucine to active Amyl alcohol in Saccharomyces cerevisiae." J Biol Chem 275(15);10937-42. PMID: 10753893

Dickinson03: Dickinson JR, Salgado LE, Hewlins MJ (2003). "The catabolism of amino acids to long chain and complex alcohols in Saccharomyces cerevisiae." J Biol Chem 278(10);8028-34. PMID: 12499363

Flikweert99: Flikweert MT, de Swaaf M, van Dijken JP, Pronk JT (1999). "Growth requirements of pyruvate-decarboxylase-negative Saccharomyces cerevisiae." FEMS Microbiol Lett 174(1);73-9. PMID: 10234824

Fulda02: Fulda M, Shockey J, Werber M, Wolter FP, Heinz E (2002). "Two long-chain acyl-CoA synthetases from Arabidopsis thaliana involved in peroxisomal fatty acid beta-oxidation." Plant J 32(1);93-103. PMID: 12366803

Hemschemeier08: Hemschemeier A, Jacobs J, Happe T (2008). "Biochemical and physiological characterization of the pyruvate formate-lyase Pfl1 of Chlamydomonas reinhardtii, a typically bacterial enzyme in a eukaryotic alga." Eukaryot Cell 7(3);518-26. PMID: 18245276

Hohmann91: Hohmann S (1991). "Characterization of PDC6, a third structural gene for pyruvate decarboxylase in Saccharomyces cerevisiae." J Bacteriol 173(24);7963-9. PMID: 1744053

Iijima96: Iijima H, Fujino T, Minekura H, Suzuki H, Kang MJ, Yamamoto T (1996). "Biochemical studies of two rat acyl-CoA synthetases, ACS1 and ACS2." Eur J Biochem 242(2);186-90. PMID: 8973631

Ioki12: Ioki M, Baba M, Bidadi H, Suzuki I, Shiraiwa Y, Watanabe MM, Nakajima N (2012). "Modes of hydrocarbon oil biosynthesis revealed by comparative gene expression analysis for race A and race B strains of Botryococcus braunii." Bioresour Technol 109;271-6. PMID: 22257857

Kalscheuer03: Kalscheuer R, Steinbuchel A (2003). "A novel bifunctional wax ester synthase/acyl-CoA:diacylglycerol acyltransferase mediates wax ester and triacylglycerol biosynthesis in Acinetobacter calcoaceticus ADP1." J Biol Chem 278(10);8075-82. PMID: 12502715

Kawamukai02: Kawamukai M (2002). "Biosynthesis, bioproduction and novel roles of ubiquinone." J Biosci Bioeng 94(6);511-7. PMID: 16233343

KillenbergJabs96: Killenberg-Jabs M, Konig S, Hohmann S, Hubner G (1996). "Purification and characterisation of the pyruvate decarboxylase from a haploid strain of Saccharomyces cerevisiae." Biol Chem Hoppe Seyler 377(5);313-7. PMID: 8828822

Kondo97: Kondo K, Horinouchi S (1997). "Characterization of the genes encoding the three-component membrane-bound alcohol dehydrogenase from Gluconobacter suboxydans and their expression in Acetobacter pasteurianus." Appl Environ Microbiol 63(3);1131-8. PMID: 9055427

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

Lee85: Lee T.C., Langston-Unkefer P.J. "Pyruvate decarboxylase from Zea mays L. I. Purification and partial characterization from mature kernels and anaerobically treated roots." Plant Physiol. (1985) 79:242-247.

Lewin01: Lewin TM, Kim JH, Granger DA, Vance JE, Coleman RA (2001). "Acyl-CoA synthetase isoforms 1, 4, and 5 are present in different subcellular membranes in rat liver and can be inhibited independently." J Biol Chem 276(27);24674-9. PMID: 11319232

Lubert: Lubert Stryer "Biochemistry." ISBN 0-7167-1226-1.

Showing only 20 references. To show more, press the button "Show all references".


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 Tue Nov 25, 2014, BIOCYC14B.