KEGG   PATHWAY: ecx00130Help
Entry
ecx00130                    Pathway                                

Name
Ubiquinone and other terpenoid-quinone biosynthesis - Escherichia coli O9 HS (commensal)
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
Ubiquinone and other terpenoid-quinone biosynthesis
ecx00130

All organismsOrtholog table
Module
Ubiquinone biosynthesis, prokaryotes, chorismate => ubiquinone [PATH:ecx00130]
Other DBs
Organism
Escherichia coli O9 HS (commensal) [GN:ecx]
Gene
ubiC; chorismate pyruvate lyase [KO:K03181] [EC:4.1.3.40]
ubiA; 4-hydroxybenzoate octaprenyltransferase [KO:K03179] [EC:2.5.1.-]
ubiD; 3-octaprenyl-4-hydroxybenzoate carboxy-lyase [KO:K03182] [EC:4.1.1.-]
ubiX; 3-octaprenyl-4-hydroxybenzoate carboxy-lyase [KO:K03186] [EC:4.1.1.-]
ubiB; ubiquinone biosynthesis protein UbiB [KO:K03688]
ubiG; 3-demethylubiquinone-9 3-methyltransferase [KO:K00568] [EC:2.1.1.64 2.1.1.222]
ubiH; 2-octaprenyl-6-methoxyphenyl hydroxylase [KO:K03185] [EC:1.14.13.-]
ubiE; ubiquinone/menaquinone biosynthesis methyltransferase [KO:K03183] [EC:2.1.1.201 2.1.1.163]
ubiF; 2-octaprenyl-3-methyl-6-methoxy-1,4-benzoquinol hydroxylase [KO:K03184] [EC:1.14.13.-]
menF; menaquinone-specific isochorismate synthase [KO:K02552] [EC:5.4.4.2]
entC; isochorismate synthase [KO:K02361] [EC:5.4.4.2]
menD; 2-succinyl-5-enolpyruvyl-6-hydroxy-3-cyclohexene-1-carboxylate synthase [KO:K02551] [EC:2.2.1.9]
acyl-CoA thioester hydrolase; K08680 2-succinyl-6-hydroxy-2,4-cyclohexadiene-1-carboxylate synthase [EC:4.2.99.20] [KO:K08680] [EC:4.2.99.20]
menC; O-succinylbenzoate synthase [KO:K02549] [EC:4.2.1.113]
menE; O-succinylbenzoic acid--CoA ligase [KO:K01911] [EC:6.2.1.26]
menB; naphthoate synthase [KO:K01661] [EC:4.1.3.36]
menA; 1,4-dihydroxy-2-naphthoate octaprenyltransferase [KO:K02548] [EC:2.5.1.- 2.5.1.74]
Compound
C00082  
L-Tyrosine
C00156  
4-Hydroxybenzoate
C00223  
p-Coumaroyl-CoA
C00251  
Chorismate
C00341  
Geranyl diphosphate
C00399  
Ubiquinone
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
C10385  
Plastoquinone-9
C10793  
Geranylhydroquinone
C13309  
2-Phytyl-1,4-naphthoquinone
C13425  
3-Hexaprenyl-4-hydroxybenzoate
C14151  
delta-Tocopherol
C14152  
beta-Tocopherol
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
C16999  
Futalosine
C17010  
de-Hypoxanthine 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
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)
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)
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)
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)
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)
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)
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)
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)
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)
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)
Reference
  Authors
Meganathan R
  Title
Ubiquinone biosynthesis in microorganisms.
  Journal
FEMS Microbiol Lett 203:131-9 (2001)
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)
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)
Reference
  Authors
Hofius D, Sonnewald U.
  Title
Vitamin E biosynthesis: biochemistry meets cell biology.
  Journal
Trends Plant Sci 8:6-8 (2003)
Reference
  Authors
Kawamukai M
  Title
Biosynthesis, bioproduction and novel roles of ubiquinone.
  Journal
J Bioscience Bioengineerinf
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)
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)
KO pathway
 

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