KEGG   PATHWAY: set00130Help
Entry
set00130                    Pathway                                

Name
Ubiquinone and other terpenoid-quinone biosynthesis - Salmonella enterica subsp. enterica serovar Enteritidis P125109
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
set00130  Ubiquinone and other terpenoid-quinone biosynthesis
set00130

Ortholog table
Module
set_M00116  Menaquinone biosynthesis, chorismate => menaquinone [PATH:set00130]
set_M00117  Ubiquinone biosynthesis, prokaryotes, chorismate => ubiquinone [PATH:set00130]
Other DBs
BSID: 75135
GO: 0006744 0009234 0042372
Organism
Salmonella enterica subsp. enterica serovar Enteritidis P125109 [GN:set]
Gene
SEN4002  ubiC; chorismate lyase [KO:K03181] [EC:4.1.3.40]
SEN4003  ubiA; 4-hydroxybenzoate octaprenyl transferase [KO:K03179] [EC:2.5.1.39]
SEN3773  yigC; conserved hypothetical protein [KO:K03182] [EC:4.1.1.98]
SEN2338  ubiX; putative decarboxylase [KO:K03186] [EC:2.5.1.129]
SEN2760  possible decarboxylase [KO:K03186] [EC:2.5.1.129]
SEN2899  visC; possible monooxygenase [KO:K18800] [EC:1.14.13.-]
SEN2258  ubiG; 3-demethylubiquinone-9 3-methyltransferase [KO:K00568] [EC:2.1.1.64 2.1.1.222]
SEN2900  ubiH; 2-octaprenyl-6-methoxyphenol hydroxylase [KO:K03185] [EC:1.14.13.-]
SEN3765  ubiE; ubiquinone/menaquinone biosynthesis methyltransferase UbiE [KO:K03183] [EC:2.1.1.201 2.1.1.163]
SEN0640  ubiF; putative monooxygenase [KO:K03184] [EC:1.14.13.-]
SEN2292  menF; isochorismate synthase [KO:K02552] [EC:5.4.4.2]
SEN0564  entC; isochorismate synthase EntC [KO:K02361] [EC:5.4.4.2]
SEN2291  menD; menaquinone biosynthesis protein [KO:K02551] [EC:2.2.1.9]
SEN2290  yfbB; conserved hypothetical protein [KO:K08680] [EC:4.2.99.20]
SEN2288  menC; O-succinylbenzoate synthase [KO:K02549] [EC:4.2.1.113]
SEN2287  menE; O-succinylbenzoic acid-CoA ligase [KO:K01911] [EC:6.2.1.26]
SEN2289  menB; naphthoate synthase [KO:K01661] [EC:4.1.3.36]
SEN1679  conserved hypothetical protein [KO:K19222] [EC:3.1.2.28]
SEN3880  menA; menaquinone biosynthetic protein [KO:K02548] [EC:2.5.1.- 2.5.1.74]
SEN0983  wraB; trp repressor binding protein [KO:K03809] [EC:1.6.5.2]
SEN4169  ytfG; conserved hypothetical protein [KO:K19267] [EC:1.6.5.2]
Compound
C00082  L-Tyrosine
C00156  4-Hydroxybenzoate
C00223  p-Coumaroyl-CoA
C00251  Chorismate
C00341  Geranyl diphosphate
C00353  Geranylgeranyl diphosphate
C00399  Ubiquinone
C00423  trans-Cinnamate
C00544  Homogentisate
C00811  4-Coumarate
C00828  Menaquinone
C00885  Isochorismate
C01179  3-(4-Hydroxyphenyl)pyruvate
C01230  all-trans-Hexaprenyl diphosphate
C01967  Ubiquinone-9
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
C03672  3-(4-Hydroxyphenyl)lactate
C03885  3-Nonaprenyl-4-hydroxybenzoate
C03993  4-(beta-D-Glucosyloxy)benzoate
C04145  all-trans-Nonaprenyl diphosphate
C04146  all-trans-Octaprenyl diphosphate
C05200  3-Hexaprenyl-4,5-dihydroxybenzoate
C05313  3-Hexaprenyl-4-hydroxy-5-methoxybenzoate
C05427  Phytyl diphosphate
C05802  2-Hexaprenyl-6-methoxyphenol
C05803  2-Hexaprenyl-6-methoxy-1,4-benzoquinone
C05804  2-Hexaprenyl-3-methyl-6-methoxy-1,4-benzoquinone
C05805  2-Hexaprenyl-3-methyl-5-hydroxy-6-methoxy-1,4-benzoquinone
C05807  2-Polyprenylphenol
C05809  3-Octaprenyl-4-hydroxybenzoate
C05810  2-Octaprenylphenol
C05811  2-Octaprenyl-6-hydroxyphenol
C05812  2-Octaprenyl-6-methoxyphenol
C05813  2-Octaprenyl-6-methoxy-1,4-benzoquinone
C05814  2-Octaprenyl-3-methyl-6-methoxy-1,4-benzoquinone
C05815  2-Octaprenyl-3-methyl-5-hydroxy-6-methoxy-1,4-benzoquinone
C05817  (1R,6R)-6-Hydroxy-2-succinylcyclohexa-2,4-diene-1-carboxylate
C05818  2-Demethylmenaquinone
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
C13425  3-Hexaprenyl-4-hydroxybenzoate
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
C17432  all-trans-Decaprenyl diphosphate
C17551  2-Polyprenyl-6-hydroxyphenol
C17552  2-Polyprenyl-6-methoxyphenol
C17554  3-Polyprenyl-4,5-dihydroxybenzoate
C17559  3-Polyprenyl-4-hydroxy-5-methoxybenzoate
C17560  2-Polyprenyl-6-methoxy-1,4-benzoquinone
C17561  2-Polyprenyl-3-methyl-6-methoxy-1,4-benzoquinone
C17562  2-Polyprenyl-3-methyl-5-hydroxy-6-methoxy-1,4-benzoquinone
C17568  Ubiquinone-6
C17569  Ubiquinone-8
C17570  2-Methyl-6-solanyl-1,4-benzoquinol
C18131  Geranyl-hydroxybenzoate
C18132  3''-Hydroxy-geranylhydroquinone
C18133  Deoxyshikonin
C18134  Dihydroechinofuran
C18135  Dihydroshikonofuran
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
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)
DOI:10.1007/s00253-003-1407-3
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)
DOI:10.1016/S0022-2836(03)00970-7
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)
DOI:10.1074/jbc.M104040200
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)
DOI:10.1016/S0005-2728(02)00396-1
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)
DOI:10.1074/jbc.M303234200
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)
DOI:10.1021/bi7023755
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)
DOI:10.1021/bi700810x
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)
DOI:10.1021/ol702126m
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)
DOI:10.1126/science.1160446
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)
DOI:10.1104/pp.106.1.271
Reference
  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
  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
  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
  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
  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
  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
  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
KO pathway
ko00130   

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