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MetaCyc Pathway: geranylgeranyl diphosphate biosynthesis

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.

Synonyms: GGPP biosynthesis

Superclasses: Biosynthesis Cofactors, Prosthetic Groups, Electron Carriers Biosynthesis Polyprenyl Biosynthesis Geranylgeranyl Diphosphate Biosynthesis

Some taxa known to possess this pathway include ? : Bacillus subtilis , Capsicum annuum , Homo sapiens , Methanothermobacter marburgensis Marburg , Micrococcus luteus , Micrococcus luteus B-P 26 , Pantoea agglomerans Inferred from experiment [Math92], Rhodobacter capsulatus , Saccharomyces cerevisiae

Expected Taxonomic Range: Archaea , Bacteria , Eukaryota

Summary:
All-trans-geranylgeranyl diphosphate (also known as geranylgeranyl pyrophosphate, or GGPP) is a crucial compound involved in the biosynthesis of a variety of terpenes and terpenoids, including central compounds such as ubiquinones and menaquinones.

In plants, geranylgeranyl diphosphate is an intermediate in the biosynthesis of essentail compounds such as chlorophylls, carotenoids, tocopherols, plastoquinones, and gibberellins [RodriguezConcep02], as well as a variety of secondary metabolites.

In addition, GGPP is also used in posttranslational modifications of proteins (geranylgeranylation) which is important for membrane adhesion as well as the function of some proteins [Caldelari01, Johnson05].

GGPP is synthesized from (2E,6E)-farnesyl diphosphate either by dedicated enzymes, such as the farnesyltranstransferase of Saccharomyces cerevisiae, or by the action of polyprenyl transferases such as the solanesyl diphosphate synthase from Rhodobacter capsulatus or octaprenyl diphosphate synthase from Escherichia coli K-12. It should be noted that the building blocks for (2E,6E)-farnesyl diphosphate are synthesized in different organisms by different pathways. While most eukaryotes and some bacteria use the mevalonate pathway I, most bacteria, as well as green algae utilize the methylerythritol phosphate pathway I (as described in the two superpathways superpathway of geranylgeranyldiphosphate biosynthesis I (via mevalonate) and superpathway of geranylgeranyl diphosphate biosynthesis II (via MEP)).

In plants, GGPP is synthesized using both routes - in the cytosol using the mevalonate pathway I, and in the plastids using the methylerythritol phosphate pathway I.

Superpathways: Methanobacterium thermoautotrophicum biosynthetic metabolism , taxadiene biosynthesis (engineered) , superpathway of geranylgeranyl diphosphate biosynthesis II (via MEP) , superpathway of geranylgeranyldiphosphate biosynthesis I (via mevalonate) , superpathway of phylloquinol biosynthesis

Unification Links: AraCyc:PWY-5120

Credits:
Created 24-Feb-2006 by Tissier C , TAIR
Revised 01-May-2008 by Caspi R , SRI International


References

Caldelari01: Caldelari D, Sternberg H, Rodriguez-Concepcion M, Gruissem W, Yalovsky S (2001). "Efficient prenylation by a plant geranylgeranyltransferase-I requires a functional CaaL box motif and a proximal polybasic domain." Plant Physiol 126(4);1416-29. PMID: 11500541

Johnson05: Johnson CD, Chary SN, Chernoff EA, Zeng Q, Running MP, Crowell DN (2005). "Protein geranylgeranyltransferase I is involved in specific aspects of abscisic acid and auxin signaling in Arabidopsis." Plant Physiol 139(2);722-33. PMID: 16183844

Math92: Math SK, Hearst JE, Poulter CD (1992). "The crtE gene in Erwinia herbicola encodes geranylgeranyl diphosphate synthase." Proc Natl Acad Sci U S A 89(15);6761-4. PMID: 1495965

Okada00: Okada K, Saito T, Nakagawa T, Kawamukai M, Kamiya Y (2000). "Five geranylgeranyl diphosphate synthases expressed in different organs are localized into three subcellular compartments in Arabidopsis." Plant Physiol 122(4);1045-56. PMID: 10759500

RodriguezConcep02: Rodriguez-Concepcion M, Boronat A (2002). "Elucidation of the methylerythritol phosphate pathway for isoprenoid biosynthesis in bacteria and plastids. A metabolic milestone achieved through genomics." Plant Physiol 130(3);1079-89. PMID: 12427975

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

Armstrong89: Armstrong GA, Alberti M, Leach F, Hearst JE (1989). "Nucleotide sequence, organization, and nature of the protein products of the carotenoid biosynthesis gene cluster of Rhodobacter capsulatus." Mol Gen Genet 216(2-3);254-68. PMID: 2747617

Armstrong90: Armstrong GA, Schmidt A, Sandmann G, Hearst JE (1990). "Genetic and biochemical characterization of carotenoid biosynthesis mutants of Rhodobacter capsulatus." J Biol Chem 265(14);8329-38. PMID: 2159477

Armstrong90a: Armstrong GA, Alberti M, Hearst JE (1990). "Conserved enzymes mediate the early reactions of carotenoid biosynthesis in nonphotosynthetic and photosynthetic prokaryotes." Proc Natl Acad Sci U S A 87(24);9975-9. PMID: 2263648

Badillo95: Badillo A, Steppuhn J, Deruere J, Camara B, Kuntz M (1995). "Structure of a functional geranylgeranyl pyrophosphate synthase gene from Capsicum annuum." Plant Mol Biol 27(2);425-8. PMID: 7888631

Bartley92: Bartley GE, Viitanen PV, Bacot KO, Scolnik PA (1992). "A tomato gene expressed during fruit ripening encodes an enzyme of the carotenoid biosynthesis pathway." J Biol Chem 267(8);5036-9. PMID: 1544888

Chen08a: Chen CKM, Hudock MP, Zhang Y, Guo RT, Cao R, No JH, Liang PH, Ko TP, Chang TH, Chang SC, Song Y, Axelson J, Kumar A, Wang AH, Oldfield E (2008). "Inhibition of geranylgeranyl diphosphate synthase by bisphosphonates: a crystallographic and computational investigation." J Med Chem 51(18);5594-607. PMID: 18800762

Chen93a: 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

Chen94b: 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

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.

Ericsson98: Ericsson J, Greene JM, Carter KC, Shell BK, Duan DR, Florence C, Edwards PA (1998). "Human geranylgeranyl diphosphate synthase: isolation of the cDNA, chromosomal mapping and tissue expression." J Lipid Res 39(9);1731-9. PMID: 9741684

IwataReuyl03a: Iwata-Reuyl D, Math SK, Desai SB, Poulter CD (2003). "Bacterial phytoene synthase: molecular cloning, expression, and characterization of Erwinia herbicola phytoene synthase." Biochemistry 42(11);3359-65. PMID: 12641468

Jiang95: Jiang Y, Proteau P, Poulter D, Ferro-Novick S (1995). "BTS1 encodes a geranylgeranyl diphosphate synthase in Saccharomyces cerevisiae." J Biol Chem 270(37);21793-9. PMID: 7665600

Kainou99: Kainou T, Kawamura K, Tanaka K, Matsuda H, Kawamukai M (1999). "Identification of the GGPS1 genes encoding geranylgeranyl diphosphate synthases from mouse and human." Biochim Biophys Acta 1437(3);333-40. PMID: 10101267

Kavanagh06: Kavanagh KL, Dunford JE, Bunkoczi G, Russell RG, Oppermann U (2006). "The crystal structure of human geranylgeranyl pyrophosphate synthase reveals a novel hexameric arrangement and inhibitory product binding." J Biol Chem 281(31);22004-12. PMID: 16698791

Kuntz92: Kuntz M, Romer S, Suire C, Hugueney P, Weil JH, Schantz R, Camara B (1992). "Identification of a cDNA for the plastid-located geranylgeranyl pyrophosphate synthase from Capsicum annuum: correlative increase in enzyme activity and transcript level during fruit ripening." Plant J 2(1);25-34. PMID: 1303794

Kuzuguchi99: Kuzuguchi T, Morita Y, Sagami I, Sagami H, Ogura K (1999). "Human geranylgeranyl diphosphate synthase. cDNA cloning and expression." J Biol Chem 274(9);5888-94. PMID: 10026212

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

Minami09: Minami A, Tajima N, Higuchi Y, Toyomasu T, Sassa T, Kato N, Dairi T (2009). "Identification and functional analysis of brassicicene C biosynthetic gene cluster in Alternaria brassicicola." Bioorg Med Chem Lett 19(3);870-4. PMID: 19097780

Saikia09: Saikia S, Scott B (2009). "Functional analysis and subcellular localization of two geranylgeranyl diphosphate synthases from Penicillium paxilli." Mol Genet Genomics 282(3);257-71. PMID: 19529962

Sitthithaworn10: Sitthithaworn W, Wungsintaweekul J, Sirisuntipong T, Charoonratana T, Ebizuka Y, De-Eknamkul W (2010). "Cloning and expression of 1-deoxy-d-xylulose 5-phosphate synthase cDNA from Croton stellatopilosus and expression of 2C-methyl-d-erythritol 4-phosphate synthase and geranylgeranyl diphosphate synthase, key enzymes of plaunotol biosynthesis." J Plant Physiol 167(4);292-300. PMID: 19782428

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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 Fri Nov 28, 2014, BIOCYC13A.