MetaCyc Pathway: plastoquinol-9 biosynthesis I
Inferred from experiment

Enzyme View:

Pathway diagram: plastoquinol-9 biosynthesis I

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: plastoquinone biosynthesis I, plastoquinone-9 biosynthesis I, plastoquinol biosynthesis I

Superclasses: BiosynthesisCofactors, Prosthetic Groups, Electron Carriers BiosynthesisQuinol and Quinone BiosynthesisPlastoquinol Biosynthesis

Some taxa known to possess this pathway include : Arabidopsis thaliana colInferred from experiment [Sadre06], Chlamydomonas reinhardtii, Spinacia oleracea

Expected Taxonomic Range: Phaeophyceae, Rhodophyta, Viridiplantae

General Background

Plastoquinones (PQ) are benzoquinone electron carriers that can function as acceptor/donor for either one or two electrons. They are analogs of ubiquinones (Coenzyme Q), with two methyl groups substituting the methoxy groups found in Q. The fully reduced form is called a plastoquinol.

Plastoquinones are found in the chloroplasts of higher plants, red, brown and green algae, and in cyanobacteria, and are important members of the photosynthetic electron transfer chain, where they carry electrons from photosystem II to the cytochrome b6f complex. In fact, it has been shown that in cyanobacteria essentially all electron transport through unbound quinones proceeds via PQ in cyanobacterial thylakoids. Apart from PQ the only quinone found in thylakoids is vitamin K1, which is associated with PS I [Vermaas01].

Plastoquinones also serve as cofactors involved in the desaturation of phytoene in the synthesis of carotenoids (see trans-lycopene biosynthesis II (plants)).

Plastoquinone was isolated originally in 1946 from alfalfa, but was not identified at the time. It was rediscovered in 1959 and its structure was described in the same year (see [Collins81]).

About This Pathway

The pathway for the biosynthesis of plastoquinone in plants starts with 4-hydroxyphenylpyruvate, which is converted to homogentisate. homogentisate is a branching point in the formation of plastoquinones and tocopherols. The committed step in plastoquinone biosynthesis is condensation of homogentisate and all-trans-nonaprenyl diphosphate, which is catalyzed by homogentisate solanyltransferase. A different enzyme ( homogentisate phytyltransferase) catalyzes the condensation of homogentisate with phytyl diphosphate, the committed step for biosynthesis of tocopherols (see vitamin E biosynthesis (tocopherols)).

The plastoquinone biosynthesis in cyanobacteria is different than that of plants (see plastoquinol-9 biosynthesis II).

Citations: [Cheng03]

Superpathways: superpathway of plastoquinol biosynthesis

Variants: plastoquinol-9 biosynthesis II

Unification Links: AraCyc:PWY-1581

Created 19-Jul-2004 by Zhang P, TAIR
Revised 23-Apr-2008 by Caspi R, SRI International


Cahoon03: Cahoon EB, Hall SE, Ripp KG, Ganzke TS, Hitz WD, Coughlan SJ (2003). "Metabolic redesign of vitamin E biosynthesis in plants for tocotrienol production and increased antioxidant content." Nat Biotechnol 21(9);1082-7. PMID: 12897790

Cheng03: Cheng Z, Sattler S, Maeda H, Sakuragi Y, Bryant DA, DellaPenna D (2003). "Highly divergent methyltransferases catalyze a conserved reaction in tocopherol and plastoquinone synthesis in cyanobacteria and photosynthetic eukaryotes." Plant Cell 15(10);2343-56. PMID: 14508009

Collins81: Collins MD, Jones D (1981). "Distribution of isoprenoid quinone structural types in bacteria and their taxonomic implication." Microbiol Rev 45(2);316-54. PMID: 7022156

Horvath: Horvath G, Wessjohann L, Bigirimana J, Monica H, Jansen M, Guisez Y, Caubergs R, Horemans N "Accumulation of tocopherols and tocotrienols during seed development of grape (Vitis vinifera L. cv. Albert Lavallee)." Plant Physiol Biochem 44(11-12);724-31. PMID: 17110122

KamalEldin96: Kamal-Eldin A, Appelqvist LA (1996). "The chemistry and antioxidant properties of tocopherols and tocotrienols." Lipids 31(7);671-701. PMID: 8827691

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

Padley94: Padley FB, Gunstone FD, Harwood JL (1994). "The Lipid Handbook." In: The Lipid Handbook, 2nd Edn. (eds. Gunstone, F.D., Harwood, J.L., and Padley, F.B.) 130 Chapman & Hall, London,.

Sadre06: Sadre R, Gruber J, Frentzen M (2006). "Characterization of homogentisate prenyltransferases involved in plastoquinone-9 and tocochromanol biosynthesis." FEBS Lett 580(22);5357-62. PMID: 16989822

Sadre10: Sadre R, Frentzen M, Saeed M, Hawkes T (2010). "Catalytic reactions of the homogentisate prenyl transferase involved in plastoquinone-9 biosynthesis." J Biol Chem 285(24);18191-8. PMID: 20400515

Soll85: Soll J, Schultz G, Joyard J, Douce R, Block MA (1985). "Localization and synthesis of prenylquinones in isolated outer and inner envelope membranes from spinach chloroplasts." Arch Biochem Biophys 238(1);290-9. PMID: 3985624

Vermaas01: Vermaas WFJ (2001). "Photosynthesis and Respiration in Cyanobacteria." Encyclopedia of Life Sciences, Macmillan Publishers Ltd, Nature Publishing Group.

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

Bradley86: Bradley FC, Lindstedt S, Lipscomb JD, Que L, Roe AL, Rundgren M (1986). "4-Hydroxyphenylpyruvate dioxygenase is an iron-tyrosinate protein." J Biol Chem 261(25);11693-6. PMID: 3017941

Brownlee04: Brownlee JM, Johnson-Winters K, Harrison DH, Moran GR (2004). "Structure of the ferrous form of (4-hydroxyphenyl)pyruvate dioxygenase from Streptomyces avermitilis in complex with the therapeutic herbicide, NTBC." Biochemistry 43(21);6370-7. PMID: 15157070

Dahnhardt02: Dahnhardt D, Falk J, Appel J, van der Kooij TA, Schulz-Friedrich R, Krupinska K (2002). "The hydroxyphenylpyruvate dioxygenase from Synechocystis sp. PCC 6803 is not required for plastoquinone biosynthesis." FEBS Lett 523(1-3);177-81. PMID: 12123828

Garcia00: Garcia I, Job D, Matringe M (2000). "Inhibition of p-hydroxyphenylpyruvate dioxygenase by the diketonitrile of isoxaflutole: a case of half-site reactivity." Biochemistry 39(25);7501-7. PMID: 10858299

Garcia99: Garcia I, Rodgers M, Pepin R, Hsieh TF, Matringe M (1999). "Characterization and subcellular compartmentation of recombinant 4-hydroxyphenylpyruvate dioxygenase from Arabidopsis in transgenic tobacco." Plant Physiol 119(4);1507-16. PMID: 10198110

Gunsior04: Gunsior M, Ravel J, Challis GL, Townsend CA (2004). "Engineering p-hydroxyphenylpyruvate dioxygenase to a p-hydroxymandelate synthase and evidence for the proposed benzene oxide intermediate in homogentisate formation." Biochemistry 43(3);663-74. PMID: 14730970

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

Lindstedt87: Lindstedt S, Odelhog B (1987). "4-Hydroxyphenylpyruvate dioxygenase from human liver." Methods Enzymol 142;139-42. PMID: 3037254

Lindstedt87a: Lindstedt S, Odelhog B (1987). "4-Hydroxyphenylpyruvate dioxygenase from Pseudomonas." Methods Enzymol 142;143-8. PMID: 3037255

Moran05: Moran GR (2005). "4-Hydroxyphenylpyruvate dioxygenase." Arch Biochem Biophys 433(1);117-28. PMID: 15581571

Motohashi03: Motohashi R, Ito T, Kobayashi M, Taji T, Nagata N, Asami T, Yoshida S, Yamaguchi-Shinozaki K, Shinozaki K (2003). "Functional analysis of the 37 kDa inner envelope membrane polypeptide in chloroplast biogenesis using a Ds-tagged Arabidopsis pale-green mutant." Plant J 34(5);719-31. PMID: 12787252

Norris98: Norris SR, Shen X, DellaPenna D (1998). "Complementation of the Arabidopsis pds1 mutation with the gene encoding p-hydroxyphenylpyruvate dioxygenase." Plant Physiol 117(4);1317-23. PMID: 9701587

Pascal85: Pascal RA, Oliver MA, Chen YC (1985). "Alternate substrates and inhibitors of bacterial 4-hydroxyphenylpyruvate dioxygenase." Biochemistry 24(13);3158-65. PMID: 4027238

Ruetschi97: Ruetschi U, Rymo L, Lindstedt S (1997). "Human 4-hydroxyphenylpyruvate dioxygenase gene (HPD)." Genomics 44(3);292-9. PMID: 9325050

Shintani02: Shintani DK, Cheng Z, DellaPenna D (2002). "The role of 2-methyl-6-phytylbenzoquinone methyltransferase in determining tocopherol composition in Synechocystis sp. PCC6803." FEBS Lett 511(1-3);1-5. PMID: 11821038

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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
Page generated by Pathway Tools version 20.0 (software by SRI International) on Thu May 5, 2016, BIOCYC13A.