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MetaCyc Pathway: polyisoprenoid biosynthesis (E. coli)

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 Cofactors, Prosthetic Groups, Electron Carriers Biosynthesis Polyprenyl Biosynthesis
Superpathways

Some taxa known to possess this pathway include ? : Escherichia coli K-12 substr. MG1655

Expected Taxonomic Range: Archaea , Bacteria , Eukaryota

Summary:
In this pathway multiple units of isopentenyl diphosphate (IPP) undergo a series of polymerizations to form various polyisoprenoids.

There are two different pathways for the biosynthesis of IPP. Bacteria that possess ubiquinone generally use the methylerythritol phosphate pathway I (MEP), while the eukaryotic microorganisms use the mevalonate pathway I. However, exceptions exist - for example, some eukaryotic microbes, like the green algae and the malarial parasite Plasmodium falciparum, appear to utilize the MEP pathway, and some bacteria utilze the mevalonate pathway [Eisenreich01, Eisenreich04].

In Escherichia coli K-12 the initial addition of two isoprenyl units to form (2E,6E)-farnesyl diphosphate is catalyzed by geranyl diphosphate synthase / farnesyl diphosphate synthase, and further polymerizations are carried out by additional enzymes, depending on the configuration. Additions in the trans configuration are carried out by octaprenyl diphosphate synthase, while addition in the cis configuration is catalyzed by undecaprenyl diphosphate synthase.

In Escherichia coli, the trans-polyisoprenoid pathway continues to form all-trans-octaprenyl diphosphate, which is utilized in the superpathway of ubiquinol-8 biosynthesis (prokaryotic) and menaquinol-8 biosynthesis pathways for formation the inner membrane electron carriers ubiquinone, menaquinone, and demethylmenaquinone.

The cis,trans-polyisoprenoid pathway continues to form di-trans,octa-cis-undecaprenyl diphosphate, the precursor for all-trans-undecaprenyl phosphate, which functions as the carrier lipid in the biosynthesis of peptidoglycan, enterobacterial common antigen and lipopolysaccharides (LPS).

Subpathways: trans, trans-farnesyl diphosphate biosynthesis , di-trans,poly-cis-undecaprenyl phosphate biosynthesis , octaprenyl diphosphate biosynthesis

Unification Links: EcoCyc:POLYISOPRENSYN-PWY

Credits:
Created 04-Sep-1996 by Riley M , Marine Biological Laboratory
Revised 15-Jan-2008 by Caspi R , SRI International


References

Eisenreich01: Eisenreich W, Rohdich F, Bacher A (2001). "Deoxyxylulose phosphate pathway to terpenoids." Trends Plant Sci 6(2);78-84. PMID: 11173292

Eisenreich04: Eisenreich W, Bacher A, Arigoni D, Rohdich F (2004). "Biosynthesis of isoprenoids via the non-mevalonate pathway." Cell Mol Life Sci 61(12);1401-26. PMID: 15197467

Meganathan01: Meganathan R (2001). "Ubiquinone biosynthesis in microorganisms." FEMS Microbiol Lett 203(2);131-9. PMID: 11583838

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

Aharoni03: Aharoni A, Giri AP, Deuerlein S, Griepink F, de Kogel WJ, Verstappen FW, Verhoeven HA, Jongsma MA, Schwab W, Bouwmeester HJ (2003). "Terpenoid metabolism in wild-type and transgenic Arabidopsis plants." Plant Cell 15(12);2866-84. PMID: 14630967

Anderson89: Anderson MS, Muehlbacher M, Street IP, Proffitt J, Poulter CD (1989). "Isopentenyl diphosphate:dimethylallyl diphosphate isomerase. An improved purification of the enzyme and isolation of the gene from Saccharomyces cerevisiae." J Biol Chem 1989;264(32);19169-75. PMID: 2681212

Anderson89a: 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

Apfel99: Apfel CM, Takacs B, Fountoulakis M, Stieger M, Keck W (1999). "Use of genomics to identify bacterial undecaprenyl pyrophosphate synthetase: cloning, expression, and characterization of the essential uppS gene." J Bacteriol 1999;181(2);483-92. PMID: 9882662

Asai94: Asai K, Fujisaki S, Nishimura Y, Nishino T, Okada K, Nakagawa T, Kawamukai M, Matsuda H (1994). "The identification of Escherichia coli ispB (cel) gene encoding the octaprenyl diphosphate synthase." Biochem Biophys Res Commun 202(1);340-5. PMID: 8037730

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

Baba85: Baba T, Muth J, Allen CM (1985). "Photoaffinity labeling of undecaprenyl pyrophosphate synthetase with a farnesyl pyrophosphate analogue." J Biol Chem 1985;260(19);10467-73. PMID: 3897217

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

Bonanno01: Bonanno JB, Edo C, Eswar N, Pieper U, Romanowski MJ, Ilyin V, Gerchman SE, Kycia H, Studier FW, Sali A, Burley SK (2001). "Structural genomics of enzymes involved in sterol/isoprenoid biosynthesis." Proc Natl Acad Sci U S A 98(23);12896-901. PMID: 11698677

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

BRENDA14: BRENDA team (2014). "Imported from BRENDA version existing on Aug 2014." http://www.brenda-enzymes.org.

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

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

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

Campbell98: Campbell M, Hahn FM, Poulter CD, Leustek T (1998). "Analysis of the isopentenyl diphosphate isomerase gene family from Arabidopsis thaliana." Plant Mol Biol 36(2);323-8. PMID: 9484444

Carrigan03: Carrigan CN, Poulter CD (2003). "Zinc is an essential cofactor for type I isopentenyl diphosphate:dimethylallyl diphosphate isomerase." J Am Chem Soc 125(30);9008-9. PMID: 15369345

Chang03: Chang SY, Chen YK, Wang AH, Liang PH (2003). "Identification of the active conformation and the importance of length of the flexible loop 72-83 in regulating the conformational change of undecaprenyl pyrophosphate synthase." Biochemistry 42(49);14452-9. PMID: 14661956

Chang03a: Chang SY, Ko TP, Liang PH, Wang AH (2003). "Catalytic mechanism revealed by the crystal structure of undecaprenyl pyrophosphate synthase in complex with sulfate, magnesium, and triton." J Biol Chem 278(31);29298-307. PMID: 12756244

Chang04b: Chang SY, Ko TP, Chen AP, Wang AH, Liang PH (2004). "Substrate binding mode and reaction mechanism of undecaprenyl pyrophosphate synthase deduced from crystallographic studies." Protein Sci 13(4);971-8. PMID: 15044730

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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, BIOCYC13B.