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MetaCyc Pathway: geranyl diphosphate biosynthesis
Inferred from experiment

Enzyme View:

Pathway diagram: geranyl diphosphate biosynthesis

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.

Synonyms: GPP biosynthesis

Superclasses: BiosynthesisCofactors, Prosthetic Groups, Electron Carriers BiosynthesisPolyprenyl Biosynthesis

Some taxa known to possess this pathway include : Arabidopsis thaliana col, Escherichia coli K-12 substr. MG1655, Hevea brasiliensis, Mentha x piperita, Methanothermobacter marburgensis Marburg, Saccharomyces cerevisiae

Expected Taxonomic Range: Archaea, Bacteria , Eukaryota

General Background

Geranyl diphosphate (geranyl pyrophosphate, GPP) is the universal precursor of several classes of compounds, including the monoterpenes, a diverse group of compounds crucial for numerous biological roles. In plants monoterpenes are involved in defence against herbivores and pathogens, allelopathic interactions and pollination.

Monoterpenes are also amongst the most important constituents of flavorings and fragrances for human consumption and can serve as therapeutic agents in human medicine (for review see [Bouvier00]). GPP is produced by geranyl pyrophosphate synthases which catalyze the condensation of isopentenyl diphosphate (isopentenyl pyrophosphate, IPP) with dimethylallyl diphosphate (DMAPP) following a head-to-tail mechanism.

In plants GPP is synthesized in plastids; IPP and DMAPP originate from the methylerythritol phosphate pathway I.

Citations: [Burke99, Burke04]

Unification Links: AraCyc:PWY-5122


Bouvier00: Bouvier F, Suire C, d'Harlingue A, Backhaus RA, Camara B (2000). "Molecular cloning of geranyl diphosphate synthase and compartmentation of monoterpene synthesis in plant cells." Plant J 24(2);241-52. PMID: 11069698

Burke04: Burke C, Klettke K, Croteau R (2004). "Heteromeric geranyl diphosphate synthase from mint: construction of a functional fusion protein and inhibition by bisphosphonate substrate analogs." Arch Biochem Biophys 422(1);52-60. PMID: 14725857

Burke99: Burke CC, Wildung MR, Croteau R (1999). "Geranyl diphosphate synthase: cloning, expression, and characterization of this prenyltransferase as a heterodimer." Proc Natl Acad Sci U S A 96(23);13062-7. PMID: 10557273

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

Anderson89: Anderson MS, Yarger JG, Burck CL, Poulter CD (1989). "Farnesyl diphosphate synthetase. Molecular cloning, sequence, and expression of an essential gene from Saccharomyces cerevisiae." J Biol Chem 1989;264(32);19176-84. PMID: 2681213

Baba06: Baba T, Ara T, Hasegawa M, Takai Y, Okumura Y, Baba M, Datsenko KA, Tomita M, Wanner BL, Mori H (2006). "Construction of Escherichia coli K-12 in-frame, single-gene knockout mutants: the Keio collection." Mol Syst Biol 2;2006.0008. PMID: 16738554

Barnard81: Barnard GF, Popjak G (1981). "Human liver prenyltransferase and its characterization." Biochim Biophys Acta 661(1);87-99. PMID: 7295734

Blanchard93: Blanchard L, Karst F (1993). "Characterization of a lysine-to-glutamic acid mutation in a conservative sequence of farnesyl diphosphate synthase from Saccharomyces cerevisiae." Gene 125(2);185-9. PMID: 8096487

Burke02: Burke C, Croteau R (2002). "Interaction with the small subunit of geranyl diphosphate synthase modifies the chain length specificity of geranylgeranyl diphosphate synthase to produce geranyl diphosphate." J Biol Chem 277(5);3141-9. PMID: 11733504

Butland05: Butland G, Peregrin-Alvarez JM, Li J, Yang W, Yang X, Canadien V, Starostine A, Richards D, Beattie B, Krogan N, Davey M, Parkinson J, Greenblatt J, Emili A (2005). "Interaction network containing conserved and essential protein complexes in Escherichia coli." Nature 433(7025);531-7. PMID: 15690043

Chen93d: Chen A, Poulter CD (1993). "Purification and characterization of farnesyl diphosphate/geranylgeranyl diphosphate synthase. A thermostable bifunctional enzyme from Methanobacterium thermoautotrophicum." J Biol Chem 268(15);11002-7. PMID: 8388380

Chen94c: Chen A, Poulter CD (1994). "Isolation and characterization of idsA: the gene for the short chain isoprenyl diphosphate synthase from Methanobacterium thermoautotrophicum." Arch Biochem Biophys 314(2);399-404. PMID: 7979381

Chooi10: Chooi YH, Cacho R, Tang Y (2010). "Identification of the viridicatumtoxin and griseofulvin gene clusters from Penicillium aethiopicum." Chem Biol 17(5);483-94. PMID: 20534346

Chooi12: Chooi YH, Fang J, Li Y, Wu K, Wang P, Tang Y (2012). "Discovery and characterization of a group of fungal polycyclic polyketide prenyltransferases." J Am Chem Soc 134(22);9428-37. PMID: 22590971

Cunillera96: Cunillera N, Arro M, Delourme D, Karst F, Boronat A, Ferrer A (1996). "Arabidopsis thaliana contains two differentially expressed farnesyl-diphosphate synthase genes." J Biol Chem 271(13);7774-80. PMID: 8631820

Daum98: Daum G, Lees ND, Bard M, Dickson R (1998). "Biochemistry, cell biology and molecular biology of lipids of Saccharomyces cerevisiae." Yeast 1998;14(16);1471-510. PMID: 9885152

Delourme94: Delourme D, Lacroute F, Karst F (1994). "Cloning of an Arabidopsis thaliana cDNA coding for farnesyl diphosphate synthase by functional complementation in yeast." Plant Mol Biol 26(6);1867-73. PMID: 7858223

DiazMejia09: Diaz-Mejia JJ, Babu M, Emili A (2009). "Computational and experimental approaches to chart the Escherichia coli cell-envelope-associated proteome and interactome." FEMS Microbiol Rev 33(1);66-97. PMID: 19054114

Dogbo87: Dogbo, O., Camara, B. (1987). "Purification of isopentenyl pyrophosphate isomerase and geranylgeranyl pyrophosphate synthase from Capsicum chromoplasts by affinity chromatography." Biochimica et Biophysica Acta (BBA) - Lipids and Lipid Metabolism 920(2):140-148.

Dozier12: Dozier JK, Distefano MD (2012). "An enzyme-coupled continuous fluorescence assay for farnesyl diphosphate synthases." Anal Biochem 421(1);158-63. PMID: 22085443

Eberhardt75: Eberhardt NL, Rilling HC (1975). "Prenyltransferase from Saccharomyces cerevisiae. Purification to homogeneity and molecular properties." J Biol Chem 1975;250(3);863-6. PMID: 234442

Fujisaki05: Fujisaki S, Takahashi I, Hara H, Horiuchi K, Nishino T, Nishimura Y (2005). "Disruption of the structural gene for farnesyl diphosphate synthase in Escherichia coli." J Biochem (Tokyo) 137(3);395-400. PMID: 15809342

Fujisaki86: Fujisaki S, Nishino T, Katsuki H (1986). "Isoprenoid synthesis in Escherichia coli. Separation and partial purification of four enzymes involved in the synthesis." J Biochem (Tokyo) 1986;99(5);1327-37. PMID: 3519603

Fujisaki89: Fujisaki S, Nishino T, Katsuki H, Hara H, Nishimura Y, Hirota Y (1989). "Isolation and characterization of an Escherichia coli mutant having temperature-sensitive farnesyl diphosphate synthase." J Bacteriol 1989;171(10);5654-8. PMID: 2676985

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

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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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