KEGG   PATHWAY: gmx00130
Entry
gmx00130                    Pathway                                
Name
Ubiquinone and other terpenoid-quinone biosynthesis - Glycine max (soybean)
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
gmx00130  Ubiquinone and other terpenoid-quinone biosynthesis
gmx00130

Module
gmx_M00112  Tocopherol/tocotorienol biosynthesis, homogentisate + phytyl/geranylgeranyl-PP => tocopherol/tocotorienol [PATH:gmx00130]
gmx_M00932  Phylloquinone biosynthesis, chorismate (+ phytyl-PP) => phylloquinol [PATH:gmx00130]
gmx_M00933  Plastoquinone biosynthesis, homogentisate + solanesyl-PP => plastoquinol [PATH:gmx00130]
Other DBs
GO: 0006744 0009234 0042372
Organism
Glycine max (soybean) [GN:gmx]
Gene
732650  tyrosine aminotransferase [KO:K00815] [EC:2.6.1.5]
100785132  probable aminotransferase TAT2 [KO:K00815] [EC:2.6.1.5]
100800830  nicotianamine aminotransferase 1 [KO:K00815] [EC:2.6.1.5]
100784392  probable aminotransferase TAT2 [KO:K00815] [EC:2.6.1.5]
100499623  C4H; trans-cinnamate 4-monooxygenase [KO:K00487] [EC:1.14.14.91]
100818985  trans-cinnamate 4-monooxygenase [KO:K00487] [EC:1.14.14.91]
100812188  C4H1; cinnamate 4-hydroxylase [KO:K00487] [EC:1.14.14.91]
100811418  4-coumarate--CoA ligase-like 1 [KO:K01904] [EC:6.2.1.12]
100797843  4CL; 4-coumarate--CoA ligase-like 7-like [KO:K01904] [EC:6.2.1.12]
547944  4CL2; 4-coumarate--CoA ligase 2 [KO:K01904] [EC:6.2.1.12]
100814237  4-coumarate--CoA ligase-like 1 [KO:K01904] [EC:6.2.1.12]
100779668  4-coumarate--CoA ligase 2 [KO:K01904] [EC:6.2.1.12]
100808944  4-coumarate--CoA ligase-like 7 isoform X1 [KO:K01904] [EC:6.2.1.12]
547492  4CL3; 4-coumarate:CoA ligase isoenzyme 3 [KO:K01904] [EC:6.2.1.12]
100780741  4-coumarate--CoA ligase 2 [KO:K01904] [EC:6.2.1.12]
548034  4CL1; 4-coumarate:coenzyme A ligase [KO:K01904] [EC:6.2.1.12]
100790396  4-coumarate--CoA ligase 2 [KO:K01904] [EC:6.2.1.12]
547930  4CL4; 4-coumarate--CoA ligase 4 [KO:K01904] [EC:6.2.1.12]
100819192  4-coumarate--CoA ligase 1 [KO:K01904] [EC:6.2.1.12]
100810418  4-coumarate--CoA ligase 1 [KO:K01904] [EC:6.2.1.12]
100804808  4-coumarate--CoA ligase-like 6 [KO:K01904] [EC:6.2.1.12]
100784234  4-coumarate--CoA ligase-like 9 [KO:K01904] [EC:6.2.1.12]
102670415  4-coumarate--CoA ligase-like 7 [KO:K01904] [EC:6.2.1.12]
100801143  4-coumarate--CoA ligase-like 9 isoform X1 [KO:K01904] [EC:6.2.1.12]
100804044  4-coumarate--CoA ligase-like 9 [KO:K01904] [EC:6.2.1.12]
100777435  4-coumarate--CoA ligase-like 9 [KO:K01904] [EC:6.2.1.12]
100797753  4-hydroxybenzoate polyprenyltransferase, mitochondrial [KO:K06125] [EC:2.5.1.39]
100807800  ubiquinone biosynthesis monooxygenase COQ6, mitochondrial [KO:K06126] [EC:1.14.13.-]
100783802  uncharacterized protein LOC100783802 [KO:K00591] [EC:2.1.1.114 2.1.1.64]
100807770  ubiquinone biosynthesis O-methyltransferase, mitochondrial [KO:K00591] [EC:2.1.1.114 2.1.1.64]
100802637  2-methoxy-6-polyprenyl-1,4-benzoquinol methylase, mitochondrial isoform X1 [KO:K06127] [EC:2.1.1.201]
100794692  2-methoxy-6-polyprenyl-1,4-benzoquinol methylase, mitochondrial-like [KO:K06127] [EC:2.1.1.201]
100804974  isochorismate synthase 2, chloroplastic isoform X1 [KO:K02552] [EC:5.4.4.2]
100799025  ICS1; isochorismate synthase 2, chloroplastic isoform X1 [KO:K02552] [EC:5.4.4.2]
100798570  protein PHYLLO, chloroplastic isoform X1 [KO:K14759] [EC:5.4.4.2 2.2.1.9 4.2.99.20 4.2.1.113]
100809925  2-succinylbenzoate--CoA ligase, chloroplastic/peroxisomal [KO:K14760] [EC:6.2.1.26]
100787691  2-succinylbenzoate--CoA ligase, chloroplastic/peroxisomal isoform X1 [KO:K14760] [EC:6.2.1.26]
100807101  uncharacterized protein LOC100807101 [KO:K01661] [EC:4.1.3.36]
100782743  1,4-dihydroxy-2-naphthoyl-CoA synthase, peroxisomal [KO:K01661] [EC:4.1.3.36]
100527403  uncharacterized protein LOC100527403 [KO:K19222] [EC:3.1.2.28]
100783241  1,4-dihydroxy-2-naphthoyl-CoA thioesterase 1 isoform X1 [KO:K19222] [EC:3.1.2.28]
100527631  uncharacterized protein LOC100527631 [KO:K19222] [EC:3.1.2.28]
100790693  1,4-dihydroxy-2-naphthoyl-CoA thioesterase 1 [KO:K19222] [EC:3.1.2.28]
100813101  2-carboxy-1,4-naphthoquinone phytyltransferase, chloroplastic [KO:K23094] [EC:2.5.1.130]
100791902  2-carboxy-1,4-naphthoquinone phytyltransferase, chloroplastic [KO:K23094] [EC:2.5.1.130]
100790629  2-carboxy-1,4-naphthoquinone phytyltransferase, chloroplastic [KO:K23094] [EC:2.5.1.130]
100788238  2-carboxy-1,4-naphthoquinone phytyltransferase, chloroplastic [KO:K23094] [EC:2.5.1.130]
100795521  alternative NAD(P)H-ubiquinone oxidoreductase C1, chloroplastic/mitochondrial [KO:K17872] [EC:1.6.5.12]
100789973  2-phytyl-1,4-beta-naphthoquinone methyltransferase, chloroplastic [KO:K23095] [EC:2.1.1.329]
100789470  2-phytyl-1,4-beta-naphthoquinone methyltransferase, chloroplastic [KO:K23095] [EC:2.1.1.329]
100499870  NAD(P)H dehydrogenase (quinone) FQR1-like isoform 1 [KO:K03809] [EC:1.6.5.2]
100500685  quinone reductase family protein [KO:K03809] [EC:1.6.5.2]
100305601  putative flavodoxin-like quinone reductase [KO:K03809] [EC:1.6.5.2]
100811224  probable NAD(P)H dehydrogenase (quinone) FQR1-like 2 [KO:K03809] [EC:1.6.5.2]
100820239  probable NAD(P)H dehydrogenase (quinone) FQR1-like 1 [KO:K03809] [EC:1.6.5.2]
100780853  NAD(P)H dehydrogenase (quinone) FQR1 [KO:K03809] [EC:1.6.5.2]
100805113  uncharacterized protein LOC100805113 [KO:K03809] [EC:1.6.5.2]
100803804  probable NAD(P)H dehydrogenase (quinone) FQR1-like 2 [KO:K03809] [EC:1.6.5.2]
100807532  probable NAD(P)H dehydrogenase (quinone) FQR1-like 2 [KO:K03809] [EC:1.6.5.2]
100499662  uncharacterized protein LOC100499662 [KO:K03809] [EC:1.6.5.2]
100788328  probable NAD(P)H dehydrogenase (quinone) FQR1-like 1 [KO:K03809] [EC:1.6.5.2]
100783867  NAD(P)H dehydrogenase (quinone) FQR1 [KO:K03809] [EC:1.6.5.2]
100789057  probable NAD(P)H dehydrogenase (quinone) FQR1-like 1 [KO:K03809] [EC:1.6.5.2]
102662143  NAD(P)H dehydrogenase (quinone) FQR1 [KO:K03809] [EC:1.6.5.2]
100796760  NAD(P)H dehydrogenase (quinone) FQR1 [KO:K03809] [EC:1.6.5.2]
100796228  NAD(P)H dehydrogenase (quinone) FQR1 [KO:K03809] [EC:1.6.5.2]
100809187  NAD(P)H dehydrogenase (quinone) FQR1-like [KO:K03809] [EC:1.6.5.2]
100793045  NAD(P)H dehydrogenase (quinone) FQR1 [KO:K03809] [EC:1.6.5.2]
100809530  probable NAD(P)H dehydrogenase (quinone) FQR1-like 2 [KO:K03809] [EC:1.6.5.2]
100788868  probable NAD(P)H dehydrogenase (quinone) FQR1-like 3 [KO:K03809] [EC:1.6.5.2]
100815952  NAD(P)H dehydrogenase (quinone) FQR1 [KO:K03809] [EC:1.6.5.2]
100795209  LOW QUALITY PROTEIN: probable NAD(P)H dehydrogenase (quinone) FQR1-like 1 [KO:K03809] [EC:1.6.5.2]
100799672  uncharacterized protein LOC100799672 [KO:K03809] [EC:1.6.5.2]
100101901  HPPD; 4-hydroxyphenylpyruvate dioxygenase long isoform, chloroplastic isoform 1 [KO:K00457] [EC:1.13.11.27]
732619  VTE2-2; homogentisate phytyltransferase VTE2-2 [KO:K12501] [EC:2.5.1.117]
106794098  homogentisate solanesyltransferase, chloroplastic [KO:K12501] [EC:2.5.1.117]
100806615  2-methyl-6-phytyl-1,4-hydroquinone methyltransferase, chloroplastic [KO:K12502] [EC:2.1.1.295]
100783986  37 kDa inner envelope membrane protein, chloroplastic-like [KO:K12502] [EC:2.1.1.295]
100788766  2-methyl-6-phytyl-1,4-hydroquinone methyltransferase, chloroplastic [KO:K12502] [EC:2.1.1.295]
100301896  G4DT; glycinol 4-dimethylallyltransferase [KO:K09833] [EC:2.5.1.115 2.5.1.116]
100819685  VTE2-1; homogentisate phytyltransferase 1, chloroplastic-like [KO:K09833] [EC:2.5.1.115 2.5.1.116]
100809827  PT03; glycinol 4-dimethylallyltransferase-like [KO:K09833] [EC:2.5.1.115 2.5.1.116]
732648  HPT1; homogentisate phytylprenyltransferase [KO:K09833] [EC:2.5.1.115 2.5.1.116]
100777517  PT01; glycinol 2-dimethylallyl transferase [KO:K09833] [EC:2.5.1.115 2.5.1.116]
100787246  PT11C; glycinol 4-dimethylallyltransferase-like [KO:K09833] [EC:2.5.1.115 2.5.1.116]
100787771  PT11B; glycinol 4-dimethylallyltransferase-like [KO:K09833] [EC:2.5.1.115 2.5.1.116]
100786181  PT11A; prenyltransferase family protein PT11a [KO:K09833] [EC:2.5.1.115 2.5.1.116]
100777408  PT10B; glycinol 4-dimethylallyltransferase-like [KO:K09833] [EC:2.5.1.115 2.5.1.116]
100786739  glycinol 4-dimethylallyltransferase-like [KO:K09833] [EC:2.5.1.115 2.5.1.116]
100777935  PT10D; glycinol 4-dimethylallyltransferase-like [KO:K09833] [EC:2.5.1.115 2.5.1.116]
100812378  G2DT; glycinol 2-dimethylallyltransferase [KO:K09833] [EC:2.5.1.115 2.5.1.116]
100809310  tocopherol cyclase, chloroplastic isoform X1 [KO:K09834] [EC:5.5.1.24]
100791679  tocopherol cyclase, chloroplastic [KO:K09834] [EC:5.5.1.24]
732543  gamma-tocopherol methyltransferase [KO:K05928] [EC:2.1.1.95]
100792443  GAMMA-TMT; gamma-tocopherol methyltransferase [KO:K05928] [EC:2.1.1.95]
100778509  probable tocopherol O-methyltransferase, chloroplastic [KO:K05928] [EC:2.1.1.95]
Compound
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
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
gmx00190  Oxidative phosphorylation
gmx00400  Phenylalanine, tyrosine and tryptophan biosynthesis
gmx00900  Terpenoid backbone biosynthesis
gmx00940  Phenylpropanoid biosynthesis
KO pathway
ko00130   

  All links  
Genome (1)   
   KEGG GENOME (1)   
Gene (96)   
   KEGG GENES (96)   
All databases (97)   

Download RDF
DBGET integrated database retrieval system