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Entry
map00130                    Pathway                                

Name
Ubiquinone and other terpenoid-quinone biosynthesis
Description
Ubiquinone (UQ), also called coenzyme Q, and plastoquinone (PQ) are electron carriers in oxidative phosphorylation and photosynthesis, respectively. The quinoid nucleus of ubiquinone is derived from the shikimate pathway; 4-hydroxybenzoate is directly formed from chorismate in bacteria, while it can be formed from either chorismate or tyrosine in yeast. The following biosynthesis of terpenoid moiety involves reactions of prenylation, decarboxylation, and three hydroxylations alternating with three methylations. The order of these reactions are somewhat different between bacteria and yeast. Phylloquinone (vitamin K1), menaquinone (vitamin K2), and tocopherol (vitamin E) are fat-soluble vitamins. Phylloquinone is a compound present in all photosynthetic plants serving as a cofactor for photosystem I-mediated electron transport. Menaquinone is an obligatory component of the electron-transfer pathway in bacteria.
Class
Metabolism; Metabolism of cofactors and vitamins
BRITE hierarchy
Pathway map
Ubiquinone and other terpenoid-quinone biosynthesis
map00130

All organismsOrtholog table
Module
M00112  
Tocopherol biosynthesis [PATH:map00130]
M00116  
Menaquinone biosynthesis, chorismate => menaquinone [PATH:map00130]
M00117  
Ubiquinone biosynthesis, prokaryotes, chorismate => ubiquinone [PATH:map00130]
M00128  
Ubiquinone biosynthesis, eukaryotes, 4-hydroxybenzoate => ubiquinone [PATH:map00130]
Disease
H00999  
Coenzyme Q10 deficiency
Other DBs
Reference
  Authors
Ward MJ, Fu QS, Rhoads KR, Yeung CH, Spormann AM, Criddle CS.
  Title
A derivative of the menaquinone precursor 1,4-dihydroxy-2-naphthoate is involved in the reductive transformation of carbon tetrachloride by aerobically grown Shewanella oneidensis MR-1.
  Journal
Appl Microbiol Biotechnol 63:571-7 (2004)
Reference
  Authors
Monzingo AF, Gao J, Qiu J, Georgiou G, Robertus JD.
  Title
The X-ray structure of Escherichia coli RraA (MenG), A protein inhibitor of RNA processing.
  Journal
J Mol Biol 332:1015-24 (2003)
Reference
  Authors
Johnson TW, Zybailov B, Jones AD, Bittl R, Zech S, Stehlik D, Golbeck JH, Chitnis PR.
  Title
Recruitment of a foreign quinone into the A1 site of photosystem I. In vivo replacement of plastoquinone-9 by media-supplemented naphthoquinones in phylloquinone biosynthetic pathway mutants of Synechocystis sp. PCC 6803.
  Journal
J Biol Chem 276:39512-21 (2001)
Reference
  Authors
Wade Johnson T, Naithani S, Stewart C Jr, Zybailov B, Daniel Jones A, Golbeck JH, Chitnis PR.
  Title
The menD and menE homologs code for 2-succinyl-6-hydroxyl-2,4-cyclohexadiene-1-carboxylate synthase and O-succinylbenzoic acid-CoA synthase in the phylloquinone biosynthetic pathway of Synechocystis sp. PCC 6803.
  Journal
Biochim Biophys Acta 1557:67-76 (2003)
Reference
  Authors
Gin P, Hsu AY, Rothman SC, Jonassen T, Lee PT, Tzagoloff A, Clarke CF.
  Title
The Saccharomyces cerevisiae COQ6 gene encodes a mitochondrial flavin-dependent monooxygenase required for coenzyme Q biosynthesis.
  Journal
J Biol Chem 278:25308-16 (2003)
Reference
  Authors
Jiang M, Chen X, Guo ZF, Cao Y, Chen M, Guo Z.
  Title
Identification and Characterization of (1R,6R)-2-Succinyl-6-hydroxy-2,4-cyclohexadiene-1-carboxylate Synthase in the Menaquinone Biosynthesis of Escherichia coli.
  Journal
Biochemistry 47:3426-34 (2008)
Reference
  Authors
Jiang M, Cao Y, Guo ZF, Chen M, Chen X, Guo Z.
  Title
Menaquinone biosynthesis in Escherichia coli: identification of 2-succinyl-5-enolpyruvyl-6-hydroxy-3-cyclohexene-1-carboxylate as a novel intermediate and re-evaluation of MenD activity.
  Journal
Biochemistry 46:10979-89 (2007)
Reference
  Authors
Jiang M, Chen M, Cao Y, Yang Y, Sze KH, Chen X, Guo Z.
  Title
Determination of the stereochemistry of 2-succinyl-5-enolpyruvyl-6-hydroxy-3- cyclohexene-1-carboxylate, a key intermediate in menaquinone biosynthesis.
  Journal
Org Lett 9:4765-7 (2007)
Reference
  Authors
Hiratsuka T, Furihata K, Ishikawa J, Yamashita H, Itoh N, Seto H, Dairi T
  Title
An alternative menaquinone biosynthetic pathway operating in microorganisms.
  Journal
Science 321:1670-3 (2008)
Reference
  Authors
Loscher R, Heide L
  Title
Biosynthesis of p-Hydroxybenzoate from p-Coumarate and p-Coumaroyl-Coenzyme A in Cell-Free Extracts of Lithospermum erythrorhizon Cell Cultures.
  Journal
Plant Physiol 106:271-279 (1994)
Reference
  Authors
Meganathan R
  Title
Ubiquinone biosynthesis in microorganisms.
  Journal
FEMS Microbiol Lett 203:131-9 (2001)
Reference
  Authors
Cheng Z, Sattler S, Maeda H, Sakuragi Y, Bryant DA, DellaPenna D
  Title
Highly divergent methyltransferases catalyze a conserved reaction in tocopherol and plastoquinone synthesis in cyanobacteria and photosynthetic eukaryotes.
  Journal
Plant Cell 15:2343-56 (2003)
Reference
  Authors
Sadre R, Gruber J, Frentzen M
  Title
Characterization of homogentisate prenyltransferases involved in plastoquinone-9 and tocochromanol biosynthesis.
  Journal
FEBS Lett 580:5357-62 (2006)
Reference
  Authors
Hofius D, Sonnewald U.
  Title
Vitamin E biosynthesis: biochemistry meets cell biology.
  Journal
Trends Plant Sci 8:6-8 (2003)
Reference
  Authors
Kawamukai M
  Title
Biosynthesis, bioproduction and novel roles of ubiquinone.
  Journal
J Bioscience Bioengineerinf
Reference
  Authors
Tie JK, Jin DY, Straight DL, Stafford DW
  Title
Functional study of the vitamin K cycle in mammalian cells.
  Journal
Blood 117:2967-74 (2011)
Reference
  Authors
Zhou L, Wang JY, Wu J, Wang J, Poplawsky A, Lin S, Zhu B, Chang C, Zhou T, Zhang LH, He YW
  Title
The diffusible factor synthase XanB2 is a bifunctional chorismatase that links the shikimate pathway to ubiquinone and xanthomonadins biosynthetic pathways.
  Journal
Mol Microbiol 87:80-93 (2013)
KO pathway
 

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