KEGG   PATHWAY: rn00130
Entry
rn00130                     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
Pathway map
rn00130  Ubiquinone and other terpenoid-quinone biosynthesis
rn00130

Module
M00112  Tocopherol/tocotorienol biosynthesis, homogentisate + phytyl/geranylgeranyl-PP => tocopherol/tocotorienol [PATH:rn00130]
M00116  Menaquinone biosynthesis, chorismate (+ polyprenyl-PP) => menaquinol [PATH:rn00130]
M00117  Ubiquinone biosynthesis, prokaryotes, chorismate (+ polyprenyl-PP) => ubiquinol [PATH:rn00130]
M00128  Ubiquinone biosynthesis, eukaryotes, 4-hydroxybenzoate + polyprenyl-PP => ubiquinone [PATH:rn00130]
M00930  Menaquinone biosynthesis, futalosine pathway [PATH:rn00130]
M00931  Menaquinone biosynthesis, modified futalosine pathway [PATH:rn00130]
M00932  Phylloquinone biosynthesis, chorismate (+ phytyl-PP) => phylloquinol [PATH:rn00130]
M00933  Plastoquinone biosynthesis, homogentisate + solanesyl-PP => plastoquinol [PATH:rn00130]
M00989  Ubiquinone biosynthesis, O2-independent, prokaryotes, chorismate (+ polyprenyl-PP) => ubiquinol [PATH:rn00130]
Other DBs
GO: 0006744 0009234 0042372
Reaction
R00734  L-tyrosine:2-oxoglutarate aminotransferase
R01301  4-hydroxybenzoyl-CoA hydrolase
R01302  chorismate pyruvate-lyase (4-hydroxybenzoate-forming)
R01304  UDP-glucose:4-hydroxybenzoate 4-O-beta-D-glucosyltransferase
R01616  4-coumarate:CoA ligase (AMP-forming)
R01717  chorismate hydroxymutase
R02253  trans-cinnamate,[reduced NADPH---hemoprotein reductase]:oxygen oxidoreductase (4-hydroxylating)
R02521  4-hydroxyphenylpyruvate:oxygen oxidoreductase (hydroxylating,decarboxylating)
R02964  NADH:menaquinone oxidoreductase
R03337  (R)-3-(4-hydroxyphenyl)lactate:NAD+ 2-oxidoreductase
R03339  (R)-3-(4-hydroxyphenyl)lactate:NADP+ 2-oxidoreductase
R03511  phylloquinone:oxidized-dithiothreitol oxidoreductase
R03816  NADH:phylloquinone oxidoreductase
R04030  O-succinylbenzoate:CoA ligase (AMP-forming)
R04031  (1R,6R)-6-hydroxy-2-succinylcyclohexa-2,4-diene-1-carboxylate hydrolyase (2-succinylbenzoate-forming)
R04985  4-hydroxy-3-polyprenylbenzoate carboxy-lyase
R04994  S-adenosyl-L-methionine:2-phytyl-1,4-naphthoquinol C-methyltransferase
R05000  polyisopentenylpyrolinate:4-hydroxybenzoate nonaprenyltransferase
R05144  peptidyl-glutamate 4-carboxylase (2-methyl-3-phytyl-1,4-naphthoquinone-epoxidizing)
R05454  
R05455  
R07236  S-adenosyl-L-methionine:gamma-tocopherol 5-O-methyltransferase
R07262  1,4-dihydroxy-2-naphthoyl-CoA hydrolase
R07263  4-(2-carboxyphenyl)-4-oxobutanoyl-CoA dehydratase (cyclizing)
R07500  phytyl-diphosphate:homogentisate phytyltransferase (decarboxylating)
R07501  S-adenosyl-L-methionine:2-methyl-6-phytyl-1,4-benzoquinol C3-methyltransferase
R07502  gamma-tocopherol lyase (decyclizing)
R07503  delta-tocopherol lyase (decyclizing)
R07504  S-adenosyl-L-methionine:delta-tocopherol 5-O-methyltransferase
R07508  
R08165  2-succinyl-5-enolpyruvyl-6-hydroxy-3-cyclohexene-1-carboxylate synthase
R08166  2-succinyl-6-hydroxy-2,4-cyclohexadiene-1-carboxylate synthase
R08587  futalosine ribohydrolase
R08588  dehypoxanthine futalosine:S-adenosyl-L-methionine oxidoreductase (cyclizing)
R08589  cyclic dehypoxanthine futalosine lyase (dihydroxyacetone-forming)
R08596  
R08766  3-(4-hydroxyphenyl)lactate hydro-lyase (4-coumarate-forming)
R08767  
R08768  2-(all-trans-polyprenyl)phenol,NADPH:oxygen oxidoreductase (6-hydroxylating)
R08769  S-adenosyl-L-methionine:2-polyprenyl-6-hydroxyphenol 6-O-methyltransferase; S-adenosyl-L-methionine:3-(all-trans-polyprenyl)benzene-1,2-diol 2-O-methyltransferase
R08770  4-hydroxy-3-all-trans-polyprenylbenzoate,ferredoxin:oxygen oxidoreductase (5-hydroxylating)
R08771  S-adenosyl-L-methionine:3,4-dihydroxy-5-polyprenylbenzoate 3-O-methyltransferase
R08772  4-hydroxy-3-methoxy-5-all-trans-polyprenylbenzoate carboxy-lyase
R08781  S-adenosyl-L-methionine:3-hydroxy-2-methoxy-5-methyl-6-(all-trans-polyprenyl)-1,4-benzoquinone 3-O-methyltransferase
R08782  all-trans-nonaprenyl-diphosphate:homogentisate nonaprenyltransferase (decarboxylating)
R09039  4-(beta-D-glucosyloxy)benzoate glucohydrolase
R09040  geranyl-diphosphate:4-hydroxybenzoate geranyltransferase
R09041  
R09042  geranylhydroquinone,[reduced NADPH---hemoprotein reductase]:oxygen oxidoreductase (3''-hydroxylating)
R09043  
R09044  
R09045  
R09046  
R09736  S-adenosyl-L-methione:demethylmenaquinol methyltransferase
R09737  S-adenosyl-L-methionine:2-methoxy-6-all-trans-polyprenyl-1,4-benzoquinol 5-C-methyltransferase
R09991  peptidyl-glutamate 4-carboxylase (menaquinone-epoxidizing)
R09992  menaquinone:oxidized-dithiothreitol oxidoreductase
R10491  S-adenosyl-L-methionine:gamma-tocotrienol 5-O-methyltransferase
R10492  S-adenosyl-L-methionine:delta-tocotrienol 5-O-methyltransferase
R10623  delta-tocotrienol lyase (decyclizing)
R10624  gamma-tocotrienol lyase (decyclizing)
R10666  chorismate hydro-lyase (3-[(1-carboxyvinyl)oxy]benzoate-forming)
R10667  S-adenosyl-L-methionine:3-[(1-carboxyvinyl)-oxy]benzoate adenosyltransferase (bicarbonate-hydrolysing, 6-amino-6-deoxyfutalosine-forming)
R10668  6-amino-6-deoxyfutalosine ribohydrolase
R10695  6-amino-6-deoxyfutalosine deaminase
R10708  geranylgeranyl-diphosphate:homogentisate geranylgeranyltransferase
R10709  S-adenosyl-L-methionine:2-methyl-6-solanyl-1,4-benzoquinol C3-methyltransferase
R10710  S-adenosyl-L-methionine:6-geranylgeranyl-2-methylbenzene-1,4-diol C3-methyltransferase
R10757  all-trans-polyprenyl-diphosphate:1,4-dihydroxy-2-naphthoate polyprenyltransferase
R11061  NADPH:demethylphylloquinone oxidoreductase
R12067  5-methoxy-2-methyl-3-(all-trans-polyprenyl)benzene-1,4-diol,acceptor:oxygen oxidoreductase (5-hydroxylating)
R12254  
R12255  phytyl-diphosphate:2-carboxy-1,4-naphthoquinone phytyltransferase
R12657  S-adenosyl-L-methionine:3-demethylubiquinol 3-O-methyltransferase
R12658  
R13408  5-methoxy-2-methyl-3-(all-trans-polyprenyl)benzoquinone,NADH:oxygen oxidoreductase (5-hydroxylating)
R13426  2-methoxy-6-(all-trans-polyprenyl)phenol,ferredoxin:oxygen oxidoreductase (4-hydroxylating)
R13439  prephenate,acceptor:2-(all-trans-polyprenyl)phenol oxidoreductase (6-hydroxylating)
R13440  2-polyprenyl-6-methoxyphenol,acceptor:2-(all-trans-polyprenyl)phenol oxidoreductase (4-hydroxylating)
R13441  5-methoxy-2-methyl-3-(all-trans-polyprenyl)benzene-1,4-diol,acceptor:2-(all-trans-polyprenyl)phenol oxidoreductase (3-hydroxylating)
R13456  
Compound
C00082  L-Tyrosine
C00156  4-Hydroxybenzoate
C00223  p-Coumaroyl-CoA
C00251  Chorismate
C00341  Geranyl diphosphate
C00353  Geranylgeranyl diphosphate
C00390  Ubiquinol
C00399  Ubiquinone
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
C17561  2-Polyprenyl-3-methyl-6-methoxy-1,4-benzoquinone
C17562  2-Polyprenyl-3-methyl-5-hydroxy-6-methoxy-1,4-benzoquinone
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  5-Methoxy-2-methyl-3-(all-trans-polyprenyl)benzene-1,4-diol
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
Reference
PMID:12908086
  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)
DOI:10.1007/s00253-003-1407-3
Reference
PMID:14499605
  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)
DOI:10.1016/S0022-2836(03)00970-7
Reference
PMID:11470786
  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)
DOI:10.1074/jbc.M104040200
Reference
PMID:12615349
  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)
DOI:10.1016/S0005-2728(02)00396-1
Reference
PMID:12721307
  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)
DOI:10.1074/jbc.M303234200
Reference
PMID:18284213
  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)
DOI:10.1021/bi7023755
Reference
PMID:17760421
  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)
DOI:10.1021/bi700810x
Reference
PMID:17956107
  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)
DOI:10.1021/ol702126m
Reference
PMID:18801996
  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)
DOI:10.1126/science.1160446
Reference
PMID:12232327
  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)
DOI:10.1104/pp.106.1.271
Reference
PMID:11583838
  Authors
Meganathan R
  Title
Ubiquinone biosynthesis in microorganisms.
  Journal
FEMS Microbiol Lett 203:131-9 (2001)
DOI:10.1111/j.1574-6968.2001.tb10831.x
Reference
PMID:14508009
  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)
DOI:10.1105/tpc.013656
Reference
PMID:16989822
  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)
DOI:10.1016/j.febslet.2006.09.002
Reference
PMID:12523993
  Authors
Hofius D, Sonnewald U.
  Title
Vitamin E biosynthesis: biochemistry meets cell biology.
  Journal
Trends Plant Sci 8:6-8 (2003)
DOI:10.1016/S1360-1385(02)00002-X
Reference
PMID:16233343
  Authors
Kawamukai M
  Title
Biosynthesis, bioproduction and novel roles of ubiquinone.
  Journal
J Biosci Bioeng 94:511-7 (2002)
DOI:10.1016/S1389-1723(02)80188-8
Reference
PMID:21239697
  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)
DOI:10.1182/blood-2010-08-304303
Reference
PMID:23113660
  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)
DOI:10.1111/mmi.12084
Related
pathway
rn00400  Phenylalanine, tyrosine and tryptophan biosynthesis
rn00900  Terpenoid backbone biosynthesis
rn00940  Phenylpropanoid biosynthesis
KO pathway
ko00130   

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