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
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]
DBLINKS     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]
            100804044  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
REL_PATHWAY gmx00190  Oxidative phosphorylation
            gmx00400  Phenylalanine, tyrosine and tryptophan biosynthesis
            gmx00900  Terpenoid backbone biosynthesis
            gmx00940  Phenylpropanoid biosynthesis
KO_PATHWAY  ko00130
///
