MetaCyc Pathway: superpathway of plastoquinol biosynthesis
Inferred from experiment

Enzyme View:

Pathway diagram: superpathway of plastoquinol 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: superpathway of plastoquinone biosynthesis

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

Some taxa known to possess this pathway include : Anabaena variabilis, Arabidopsis thaliana col, Chlorogloeopsis fritschii, Desmonostoc muscorum, Mastigocladus laminosus, Spinacia oleracea, Synechococcus elongatus PCC 6301, Synechococcus elongatus PCC 7942, Synechocystis sp. PCC 6803

Expected Taxonomic Range: Cyanobacteria, Phaeophyceae, Rhodophyta, Viridiplantae

Plastoquinone, like ubiquinone, is a benzoquinone electron carrier. Plastoquinone is a member of the photosynthetic electron transport chain and is also a cofactor involved in the desaturation of phytoene in the synthesis of carotenoid, a photosynthetic pigment. It is found in higher plants, cyanobacteria and red, brown and green algae.

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

The committed step in plastoquinone biosynthesis is condensation of homogentisate (providing the aromatic head) and all-trans-nonaprenyl diphosphate (providing the hydrophobic prenyl tail). An analogous reaction is found in the pathway for vitamin E biosynthesis (tocopherols).

There is some indication that the pathway for plastoquinone biosynthesis in cyanobacteria may be different than that of plants. Inactivation of the cyanobacterial 4-hydroxyphenylpyruvate dioxygenase, which catalyzes the conversion of 4-hydroxyphenylpyruvate to homogentisate, while abolishing tocopherol biosynthesis, had no effect on the synthesis of plastoquinone [Dahnhardt02]. This finding suggests that plastoquinone may be synthesized in cyanobacteria by a different pathway. However, such an alternative pathway has not been described.

Subpathways: plastoquinol-9 biosynthesis I, nonaprenyl diphosphate biosynthesis I, 4-hydroxyphenylpyruvate biosynthesis

Variants: plastoquinol-9 biosynthesis II

Created 18-Mar-2008 by Caspi R, SRI International


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

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

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

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

Andersson82: Andersson SM, Pispa JP (1982). "Purification and properties of human liver tyrosine aminotransferase." Clin Chim Acta 125(2);117-23. PMID: 6128088

Blakley77: Blakley ER (1977). "The catabolism of L-tyrosine by an Arthrobacter sp." Can J Microbiol 23(9);1128-39. PMID: 20216

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

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

Collier72: Collier RH, Kohlhaw G (1972). "Nonidentity of the aspartate and the aromatic aminotransferase components of transaminase A in Escherichia coli." J Bacteriol 1972;112(1);365-71. PMID: 4404056

DeEknamkul87: De-Eknamkul W, Ellis BE (1987). "Purification and characterization of tyrosine aminotransferase activities from Anchusa officinalis cell cultures." Arch Biochem Biophys 257(2);430-8. PMID: 2889425

DeEknamkul87a: De-Eknamkul W, Ellis BE (1987). "Tyrosine aminotransferase: the entrypoint enzyme of the tyrosine-derived pathway in rosmarinic acid biosynthesis." Phytochemistry, 26(7), 1941-1946.

Dietrich91: Dietrich JB, Lorber B, Kern D (1991). "Expression of mammalian tyrosine aminotransferase in Saccharomyces cerevisiae and Escherichia coli. Purification to homogeneity and characterization of the enzyme overproduced in the bacteria." Eur J Biochem 201(2);399-407. PMID: 1682148

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

Gelfand77: Gelfand DH, Steinberg RA (1977). "Escherichia coli mutants deficient in the aspartate and aromatic amino acid aminotransferases." J Bacteriol 1977;130(1);429-40. PMID: 15983

Gu98: Gu W, Song J, Bonner CA, Xie G, Jensen RA (1998). "PhhC is an essential aminotransferase for aromatic amino acid catabolism in Pseudomonas aeruginosa." Microbiology 144 ( Pt 11);3127-34. PMID: 9846749

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 Pseudomonas." Methods Enzymol 142;143-8. PMID: 3037255

Lindstedt87a: Lindstedt S, Odelhog B (1987). "4-Hydroxyphenylpyruvate dioxygenase from human liver." Methods Enzymol 142;139-42. PMID: 3037254

Mavrides75: Mavrides C, Orr W (1975). "Multispecific aspartate and aromatic amino acid aminotransferases in Escherichia coli." J Biol Chem 250(11);4128-33. PMID: 236311

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

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

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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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