KEGG   PATHWAY: ko00130
ko00130                     Pathway                                

Ubiquinone and other terpenoid-quinone biosynthesis
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.
Metabolism; Metabolism of cofactors and vitamins
Pathway map
ko00130  Ubiquinone and other terpenoid-quinone biosynthesis

M00112  Tocopherol/tocotorienol biosynthesis, homogentisate + phytyl/geranylgeranyl-PP => tocopherol/tocotorienol [PATH:ko00130]
M00116  Menaquinone biosynthesis, chorismate (+ polyprenyl-PP) => menaquinol [PATH:ko00130]
M00117  Ubiquinone biosynthesis, prokaryotes, chorismate (+ polyprenyl-PP) => ubiquinol [PATH:ko00130]
M00128  Ubiquinone biosynthesis, eukaryotes, 4-hydroxybenzoate + polyprenyl-PP => ubiquinol [PATH:ko00130]
M00930  Menaquinone biosynthesis, futalosine pathway [PATH:ko00130]
M00931  Menaquinone biosynthesis, modified futalosine pathway [PATH:ko00130]
M00932  Phylloquinone biosynthesis, chorismate (+ phytyl-PP) => phylloquinol [PATH:ko00130]
M00933  Plastoquinone biosynthesis, homogentisate + solanesyl-PP => plastoquinol [PATH:ko00130]
Other DBs
GO: 0006744 0009234 0042372
K00815  tyrosine aminotransferase [EC:]
K00838  aromatic amino acid aminotransferase I / 2-aminoadipate transaminase [EC:]
K18606  hydroxyphenylpyruvate reductase [EC:]
K00487  trans-cinnamate 4-monooxygenase [EC:]
K01904  4-coumarate--CoA ligase [EC:]
K01075  4-hydroxybenzoyl-CoA thioesterase [EC:]
K03181  chorismate lyase [EC:]
K18240  chorismate lyase / 3-hydroxybenzoate synthase [EC:]
K03179  4-hydroxybenzoate polyprenyltransferase [EC:]
K03182  4-hydroxy-3-polyprenylbenzoate decarboxylase [EC:]
K03186  flavin prenyltransferase [EC:]
K18800  2-polyprenylphenol 6-hydroxylase [EC:]
K00568  2-polyprenyl-6-hydroxyphenyl methylase / 3-demethylubiquinone-9 3-methyltransferase [EC:]
K03185  2-octaprenyl-6-methoxyphenol hydroxylase [EC:1.14.13.-]
K03183  demethylmenaquinone methyltransferase / 2-methoxy-6-polyprenyl-1,4-benzoquinol methylase [EC:]
K03184  3-demethoxyubiquinol 3-hydroxylase [EC:]
K06125  4-hydroxybenzoate polyprenyltransferase [EC:]
K06126  ubiquinone biosynthesis monooxygenase Coq6 [EC:1.14.13.-]
K00591  polyprenyldihydroxybenzoate methyltransferase / 3-demethylubiquinol 3-O-methyltransferase [EC:]
K06127  2-methoxy-6-polyprenyl-1,4-benzoquinol methylase [EC:]
K06134  3-demethoxyubiquinol 3-hydroxylase [EC:]
K01851  salicylate biosynthesis isochorismate synthase [EC:]
K02552  menaquinone-specific isochorismate synthase [EC:]
K02361  isochorismate synthase [EC:]
K02551  2-succinyl-5-enolpyruvyl-6-hydroxy-3-cyclohexene-1-carboxylate synthase [EC:]
K08680  2-succinyl-6-hydroxy-2,4-cyclohexadiene-1-carboxylate synthase [EC:]
K02549  o-succinylbenzoate synthase [EC:]
K14759  isochorismate synthase / 2-succinyl-5-enolpyruvyl-6-hydroxy-3-cyclohexene-1-carboxylate synthase / 2-succinyl-6-hydroxy-2,4-cyclohexadiene-1-carboxylate synthase / o-succinylbenzoate synthase [EC:]
K01911  o-succinylbenzoate---CoA ligase [EC:]
K14760  o-succinylbenzoate---CoA ligase [EC:]
K01661  naphthoate synthase [EC:]
K12073  1,4-dihydroxy-2-naphthoyl-CoA hydrolase [EC:]
K19222  1,4-dihydroxy-2-naphthoyl-CoA hydrolase [EC:]
K02548  1,4-dihydroxy-2-naphthoate polyprenyltransferase [EC:]
K23094  2-carboxy-1,4-naphthoquinone phytyltransferase [EC:]
K17872  demethylphylloquinone reductase [EC:]
K23095  demethylphylloquinol methyltransferase [EC:]
K11782  chorismate dehydratase [EC:]
K18285  aminodeoxyfutalosine synthase [EC:]
K18286  aminodeoxyfutalosine deaminase [EC:]
K20810  aminodeoxyfutalosine deaminase [EC:]
K11783  futalosine hydrolase [EC:]
K18284  adenosylhomocysteine/aminodeoxyfutalosine nucleosidase [EC:]
K11784  cyclic dehypoxanthinyl futalosine synthase [EC:]
K11785  1,4-dihydroxy-6-naphthoate synthase [EC:1.14.-.-]
K00355  NAD(P)H dehydrogenase (quinone) [EC:]
K03809  NAD(P)H dehydrogenase (quinone) [EC:]
K19267  NAD(P)H dehydrogenase (quinone) [EC:]
K10106  vitamin K-dependent gamma-carboxylase [EC:]
K05357  vitamin-K-epoxide reductase (warfarin-sensitive) [EC:]
K00457  4-hydroxyphenylpyruvate dioxygenase [EC:]
K12501  homogentisate solanesyltransferase [EC:]
K12502  MPBQ/MSBQ methyltransferase [EC:]
K18534  MPBQ/MSBQ methyltransferase [EC:]
K09833  homogentisate phytyltransferase / homogentisate geranylgeranyltransferase [EC:]
K09834  tocopherol cyclase [EC:]
K05928  tocopherol O-methyltransferase [EC:]
K13565  4-hydroxybenzoate geranyltransferase [EC:]
K24441  geranylhydroquinone 3''-hydroxylase [EC:]
C00082  L-Tyrosine
C00156  4-Hydroxybenzoate
C00223  p-Coumaroyl-CoA
C00251  Chorismate
C00341  Geranyl diphosphate
C00353  Geranylgeranyl diphosphate
C00390  Ubiquinol
C00423  trans-Cinnamate
C00544  Homogentisate
C00811  4-Coumarate
C00828  Menaquinone
C00885  Isochorismate
C01179  3-(4-Hydroxyphenyl)pyruvate
C02059  Phylloquinone
C02477  alpha-Tocopherol
C02483  gamma-Tocopherol
C02730  2-Succinylbenzoate
C02949  4-Hydroxybenzoyl-CoA
C03160  2-Succinylbenzoyl-CoA
C03313  Phylloquinol
C03657  1,4-Dihydroxy-2-naphthoate
C03964  (R)-3-(4-Hydroxyphenyl)lactate
C03993  4-(beta-D-Glucosyloxy)benzoate
C04145  all-trans-Nonaprenyl diphosphate
C05427  Phytyl diphosphate
C05807  2-Polyprenylphenol
C05817  (1R,6R)-6-Hydroxy-2-succinylcyclohexa-2,4-diene-1-carboxylate
C05819  Menaquinol
C05847  all-trans-Polyprenyl diphosphate
C05848  4-Hydroxy-3-polyprenylbenzoate
C05849  Vitamin K1 epoxide
C06986  Spirodilactone
C10793  Geranylhydroquinone
C13309  2-Phytyl-1,4-naphthoquinone
C14151  delta-Tocopherol
C14152  beta-Tocopherol
C14153  alpha-Tocotrienol
C14154  beta-Tocotrienol
C14155  gamma-Tocotrienol
C14156  delta-Tocotrienol
C15547  1,4-Dihydroxy-2-naphthoyl-CoA
C15882  2-Methyl-6-phytylquinol
C15883  2,3-Dimethyl-5-phytylquinol
C16519  2-Succinyl-5-enolpyruvyl-6-hydroxy-3-cyclohexene-1-carboxylate
C16695  Plastoquinol-9
C16999  Futalosine
C17010  Dehypoxanthine futalosine
C17017  Cyclic dehypoxanthine futalosine
C17018  1,4-Dihydroxy-6-naphthoate
C17412  Shikonin
C17551  2-Polyprenyl-6-hydroxyphenol
C17552  2-Polyprenyl-6-methoxyphenol
C17554  3,4-Dihydroxy-5-polyprenylbenzoate
C17559  3-Methoxy-4-hydroxy-5-polyprenylbenzoate
C17570  2-Methyl-6-solanyl-1,4-benzoquinol
C18131  Geranyl-hydroxybenzoate
C18132  3''-Hydroxy-geranylhydroquinone
C18133  Deoxyshikonin
C18134  Dihydroechinofuran
C18135  Dihydroshikonofuran
C19847  Demethylmenaquinol
C19858  2-Methoxy-6-all-trans-polyprenyl-1,4-benzoquinol
C19859  6-Methoxy-3-methyl-2-all-trans-polyprenyl-1,4-benzoquinol
C20265  2,3-Epoxymenaquinone
C20737  6-Geranylgeranyl-2-methylbenzene-1,4-diol
C20738  6-Geranylgeranyl-2,3-dimethylbenzene-1,4-diol
C20772  3-[(1-Carboxyvinyl)oxy]benzoate
C20773  6-Amino-6-deoxyfutalosine
C21084  Demethylphylloquinol
C21860  3-Demethylubiquinol
C22039  2-Carboxy-1,4-naphthoquinone
Ward MJ, Fu QS, Rhoads KR, Yeung CH, Spormann AM, Criddle CS.
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.
Appl Microbiol Biotechnol 63:571-7 (2004)
Monzingo AF, Gao J, Qiu J, Georgiou G, Robertus JD.
The X-ray structure of Escherichia coli RraA (MenG), A protein inhibitor of RNA processing.
J Mol Biol 332:1015-24 (2003)
Johnson TW, Zybailov B, Jones AD, Bittl R, Zech S, Stehlik D, Golbeck JH, Chitnis PR.
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.
J Biol Chem 276:39512-21 (2001)
Wade Johnson T, Naithani S, Stewart C Jr, Zybailov B, Daniel Jones A, Golbeck JH, Chitnis PR.
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.
Biochim Biophys Acta 1557:67-76 (2003)
Gin P, Hsu AY, Rothman SC, Jonassen T, Lee PT, Tzagoloff A, Clarke CF.
The Saccharomyces cerevisiae COQ6 gene encodes a mitochondrial flavin-dependent monooxygenase required for coenzyme Q biosynthesis.
J Biol Chem 278:25308-16 (2003)
Jiang M, Chen X, Guo ZF, Cao Y, Chen M, Guo Z.
Identification and Characterization of (1R,6R)-2-Succinyl-6-hydroxy-2,4-cyclohexadiene-1-carboxylate Synthase in the Menaquinone Biosynthesis of Escherichia coli.
Biochemistry 47:3426-34 (2008)
Jiang M, Cao Y, Guo ZF, Chen M, Chen X, Guo Z.
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.
Biochemistry 46:10979-89 (2007)
Jiang M, Chen M, Cao Y, Yang Y, Sze KH, Chen X, Guo Z.
Determination of the stereochemistry of 2-succinyl-5-enolpyruvyl-6-hydroxy-3- cyclohexene-1-carboxylate, a key intermediate in menaquinone biosynthesis.
Org Lett 9:4765-7 (2007)
Hiratsuka T, Furihata K, Ishikawa J, Yamashita H, Itoh N, Seto H, Dairi T
An alternative menaquinone biosynthetic pathway operating in microorganisms.
Science 321:1670-3 (2008)
Loscher R, Heide L
Biosynthesis of p-Hydroxybenzoate from p-Coumarate and p-Coumaroyl-Coenzyme A in Cell-Free Extracts of Lithospermum erythrorhizon Cell Cultures.
Plant Physiol 106:271-279 (1994)
Meganathan R
Ubiquinone biosynthesis in microorganisms.
FEMS Microbiol Lett 203:131-9 (2001)
Cheng Z, Sattler S, Maeda H, Sakuragi Y, Bryant DA, DellaPenna D
Highly divergent methyltransferases catalyze a conserved reaction in tocopherol and plastoquinone synthesis in cyanobacteria and photosynthetic eukaryotes.
Plant Cell 15:2343-56 (2003)
Sadre R, Gruber J, Frentzen M
Characterization of homogentisate prenyltransferases involved in plastoquinone-9 and tocochromanol biosynthesis.
FEBS Lett 580:5357-62 (2006)
Hofius D, Sonnewald U.
Vitamin E biosynthesis: biochemistry meets cell biology.
Trends Plant Sci 8:6-8 (2003)
Kawamukai M
Biosynthesis, bioproduction and novel roles of ubiquinone.
J Biosci Bioeng 94:511-7 (2002)
Tie JK, Jin DY, Straight DL, Stafford DW
Functional study of the vitamin K cycle in mammalian cells.
Blood 117:2967-74 (2011)
Zhou L, Wang JY, Wu J, Wang J, Poplawsky A, Lin S, Zhu B, Chang C, Zhou T, Zhang LH, He YW
The diffusible factor synthase XanB2 is a bifunctional chorismatase that links the shikimate pathway to ubiquinone and xanthomonadins biosynthetic pathways.
Mol Microbiol 87:80-93 (2013)
ko00190  Oxidative phosphorylation
ko00400  Phenylalanine, tyrosine and tryptophan biosynthesis
ko00900  Terpenoid backbone biosynthesis
ko00940  Phenylpropanoid biosynthesis
ko04610  Complement and coagulation cascades

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