KEGG PATHWAY: psom00130

KEGG

PATHWAY: psom00130

Entry

psom00130                   Pathway

Name

Ubiquinone and other terpenoid-quinone biosynthesis - Papaver somniferum (opium poppy)

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

Ubiquinone and other terpenoid-quinone biosynthesis

Module

Tocopherol/tocotorienol biosynthesis, homogentisate + phytyl/geranylgeranyl-PP => tocopherol/tocotorienol [PATH:psom00130]

Phylloquinone biosynthesis, chorismate (+ phytyl-PP) => phylloquinol [PATH:psom00130]

Plastoquinone biosynthesis, homogentisate + solanesyl-PP => plastoquinol [PATH:psom00130]

Other DBs

GO:	0006744 0009234 0042372

Organism

Papaver somniferum (opium poppy) [GN:psom]

Gene

probable aminotransferase TAT2 [KO:K00815] [EC:2.6.1.5]

probable aminotransferase TAT2 [KO:K00815] [EC:2.6.1.5]

probable aminotransferase TAT2 [KO:K00815] [EC:2.6.1.5]

probable aminotransferase TAT2 [KO:K00815] [EC:2.6.1.5]

probable aminotransferase TAT2 [KO:K00815] [EC:2.6.1.5]

probable aminotransferase TAT2 [KO:K00815] [EC:2.6.1.5]

probable aminotransferase TAT2 [KO:K00815] [EC:2.6.1.5]

probable aminotransferase TAT2 [KO:K00815] [EC:2.6.1.5]

probable aminotransferase TAT2 [KO:K00815] [EC:2.6.1.5]

probable aminotransferase TAT2 [KO:K00815] [EC:2.6.1.5]

probable aminotransferase TAT2 [KO:K00815] [EC:2.6.1.5]

probable aminotransferase TAT2 [KO:K00815] [EC:2.6.1.5]

hydroxyphenylpyruvate reductase-like [KO:K18606] [EC:1.1.1.237]

hydroxyphenylpyruvate reductase-like [KO:K18606] [EC:1.1.1.237]

trans-cinnamate 4-monooxygenase [KO:K00487] [EC:1.14.14.91]

trans-cinnamate 4-monooxygenase-like [KO:K00487] [EC:1.14.14.91]

4-coumarate--CoA ligase 2-like [KO:K01904] [EC:6.2.1.12]

4-coumarate--CoA ligase-like 6 [KO:K01904] [EC:6.2.1.12]

4-coumarate--CoA ligase 2-like [KO:K01904] [EC:6.2.1.12]

4-coumarate--CoA ligase 2-like [KO:K01904] [EC:6.2.1.12]

4-coumarate--CoA ligase 2-like [KO:K01904] [EC:6.2.1.12]

4-coumarate--CoA ligase 2-like [KO:K01904] [EC:6.2.1.12]

4-coumarate--CoA ligase-like 1 [KO:K01904] [EC:6.2.1.12]

4-coumarate--CoA ligase-like 1 [KO:K01904] [EC:6.2.1.12]

4-coumarate--CoA ligase-like 7 [KO:K01904] [EC:6.2.1.12]

4-coumarate--CoA ligase-like 7 [KO:K01904] [EC:6.2.1.12]

4-coumarate--CoA ligase-like 7 [KO:K01904] [EC:6.2.1.12]

4-coumarate--CoA ligase 2-like [KO:K01904] [EC:6.2.1.12]

4-coumarate--CoA ligase 2-like [KO:K01904] [EC:6.2.1.12]

4-coumarate--CoA ligase-like 9 [KO:K01904] [EC:6.2.1.12]

4-coumarate--CoA ligase-like 9 [KO:K01904] [EC:6.2.1.12]

4-coumarate--CoA ligase-like 9 [KO:K01904] [EC:6.2.1.12]

4-coumarate--CoA ligase-like 9 [KO:K01904] [EC:6.2.1.12]

4-hydroxybenzoate polyprenyltransferase, mitochondrial-like [KO:K06125] [EC:2.5.1.39]

4-hydroxybenzoate polyprenyltransferase, mitochondrial-like [KO:K06125] [EC:2.5.1.39]

ubiquinone biosynthesis monooxygenase COQ6, mitochondrial-like isoform X1 [KO:K06126] [EC:1.14.13.-]

ubiquinone biosynthesis monooxygenase COQ6, mitochondrial-like [KO:K06126] [EC:1.14.13.-]

ubiquinone biosynthesis O-methyltransferase, mitochondrial-like [KO:K00591] [EC:2.1.1.114 2.1.1.64]

ubiquinone biosynthesis O-methyltransferase, mitochondrial-like [KO:K00591] [EC:2.1.1.114 2.1.1.64]

2-methoxy-6-polyprenyl-1,4-benzoquinol methylase, mitochondrial-like [KO:K06127] [EC:2.1.1.201]

2-methoxy-6-polyprenyl-1,4-benzoquinol methylase, mitochondrial-like [KO:K06127] [EC:2.1.1.201]

isochorismate synthase 2, chloroplastic-like [KO:K02552] [EC:5.4.4.2]

isochorismate synthase 1, chloroplastic-like [KO:K02552] [EC:5.4.4.2]

protein PHYLLO, chloroplastic-like isoform X1 [KO:K14759] [EC:5.4.4.2 2.2.1.9 4.2.99.20 4.2.1.113]

protein PHYLLO, chloroplastic-like isoform X1 [KO:K14759] [EC:5.4.4.2 2.2.1.9 4.2.99.20 4.2.1.113]

2-succinylbenzoate--CoA ligase, chloroplastic/peroxisomal [KO:K14760] [EC:6.2.1.26]

2-succinylbenzoate--CoA ligase, chloroplastic/peroxisomal-like [KO:K14760] [EC:6.2.1.26]

1,4-dihydroxy-2-naphthoyl-CoA synthase, peroxisomal-like [KO:K01661] [EC:4.1.3.36]

1,4-dihydroxy-2-naphthoyl-CoA synthase, peroxisomal-like [KO:K01661] [EC:4.1.3.36]

1,4-dihydroxy-2-naphthoyl-CoA synthase, peroxisomal-like [KO:K01661] [EC:4.1.3.36]

uncharacterized protein LOC113339487 [KO:K01661] [EC:4.1.3.36]

uncharacterized protein LOC113339488 [KO:K01661] [EC:4.1.3.36]

uncharacterized protein LOC113339490 [KO:K01661] [EC:4.1.3.36]

uncharacterized protein LOC113324423 isoform X1 [KO:K01661] [EC:4.1.3.36]

1,4-dihydroxy-2-naphthoyl-CoA synthase-like [KO:K01661] [EC:4.1.3.36]

uncharacterized protein LOC113312695 [KO:K01661] [EC:4.1.3.36]

uncharacterized protein LOC113361944 [KO:K01661] [EC:4.1.3.36]

1,4-dihydroxy-2-naphthoyl-CoA synthase, peroxisomal-like [KO:K01661] [EC:4.1.3.36]

1,4-dihydroxy-2-naphthoyl-CoA thioesterase 1-like [KO:K19222] [EC:3.1.2.28]

1,4-dihydroxy-2-naphthoyl-CoA thioesterase 1-like [KO:K19222] [EC:3.1.2.28]

2-carboxy-1,4-naphthoquinone phytyltransferase, chloroplastic-like [KO:K23094] [EC:2.5.1.130]

2-carboxy-1,4-naphthoquinone phytyltransferase, chloroplastic-like isoform X1 [KO:K23094] [EC:2.5.1.130]

alternative NAD(P)H-ubiquinone oxidoreductase C1, chloroplastic/mitochondrial-like [KO:K17872] [EC:1.6.5.12]

alternative NAD(P)H-ubiquinone oxidoreductase C1, chloroplastic/mitochondrial-like [KO:K17872] [EC:1.6.5.12]

2-phytyl-1,4-beta-naphthoquinone methyltransferase, chloroplastic-like [KO:K23095] [EC:2.1.1.329]

2-phytyl-1,4-beta-naphthoquinone methyltransferase, chloroplastic-like isoform X1 [KO:K23095] [EC:2.1.1.329]

probable NAD(P)H dehydrogenase (quinone) FQR1-like 2 [KO:K03809] [EC:1.6.5.2]

probable NAD(P)H dehydrogenase (quinone) FQR1-like 3 isoform X1 [KO:K03809] [EC:1.6.5.2]

probable NAD(P)H dehydrogenase (quinone) FQR1-like 1 [KO:K03809] [EC:1.6.5.2]

probable NAD(P)H dehydrogenase (quinone) FQR1-like 1 [KO:K03809] [EC:1.6.5.2]

probable NAD(P)H dehydrogenase (quinone) FQR1-like 3 [KO:K03809] [EC:1.6.5.2]

probable NAD(P)H dehydrogenase (quinone) FQR1-like 3 [KO:K03809] [EC:1.6.5.2]

probable NAD(P)H dehydrogenase (quinone) FQR1-like 2 [KO:K03809] [EC:1.6.5.2]

probable NAD(P)H dehydrogenase (quinone) FQR1-like 1 [KO:K03809] [EC:1.6.5.2]

4-hydroxyphenylpyruvate dioxygenase-like isoform X1 [KO:K00457] [EC:1.13.11.27]

4-hydroxyphenylpyruvate dioxygenase-like [KO:K00457] [EC:1.13.11.27]

4-hydroxyphenylpyruvate dioxygenase-like [KO:K00457] [EC:1.13.11.27]

4-hydroxyphenylpyruvate dioxygenase-like [KO:K00457] [EC:1.13.11.27]

4-hydroxyphenylpyruvate dioxygenase-like [KO:K00457] [EC:1.13.11.27]

4-hydroxyphenylpyruvate dioxygenase-like [KO:K00457] [EC:1.13.11.27]

4-hydroxyphenylpyruvate dioxygenase-like [KO:K00457] [EC:1.13.11.27]

homogentisate solanesyltransferase, chloroplastic-like [KO:K12501] [EC:2.5.1.117]

2-methyl-6-phytyl-1,4-hydroquinone methyltransferase, chloroplastic-like [KO:K12502] [EC:2.1.1.295]

2-methyl-6-phytyl-1,4-hydroquinone methyltransferase, chloroplastic-like [KO:K12502] [EC:2.1.1.295]

2-methyl-6-phytyl-1,4-hydroquinone methyltransferase, chloroplastic-like [KO:K12502] [EC:2.1.1.295]

2-methyl-6-phytyl-1,4-hydroquinone methyltransferase, chloroplastic-like isoform X1 [KO:K12502] [EC:2.1.1.295]

homogentisate phytyltransferase 1, chloroplastic-like [KO:K09833] [EC:2.5.1.115 2.5.1.116]

probable homogentisate phytyltransferase 1, chloroplastic [KO:K09833] [EC:2.5.1.115 2.5.1.116]

homogentisate phytyltransferase 1, chloroplastic-like [KO:K09833] [EC:2.5.1.115 2.5.1.116]

tocopherol cyclase, chloroplastic-like [KO:K09834] [EC:5.5.1.24]

tocopherol cyclase, chloroplastic-like [KO:K09834] [EC:5.5.1.24]

probable tocopherol O-methyltransferase, chloroplastic [KO:K05928] [EC:2.1.1.95]

probable tocopherol O-methyltransferase, chloroplastic [KO:K05928] [EC:2.1.1.95]

Compound

L-Tyrosine

4-Hydroxybenzoate

p-Coumaroyl-CoA

Chorismate

Geranyl diphosphate

Geranylgeranyl diphosphate

Ubiquinol

trans-Cinnamate

Homogentisate

4-Coumarate

Menaquinone

Isochorismate

3-(4-Hydroxyphenyl)pyruvate

Phylloquinone

alpha-Tocopherol

gamma-Tocopherol

2-Succinylbenzoate

4-Hydroxybenzoyl-CoA

2-Succinylbenzoyl-CoA

Phylloquinol

1,4-Dihydroxy-2-naphthoate

(R)-3-(4-Hydroxyphenyl)lactate

4-(beta-D-Glucosyloxy)benzoate

all-trans-Nonaprenyl diphosphate

Phytyl diphosphate

2-Polyprenylphenol

(1R,6R)-6-Hydroxy-2-succinylcyclohexa-2,4-diene-1-carboxylate

Menaquinol

all-trans-Polyprenyl diphosphate

4-Hydroxy-3-polyprenylbenzoate

Vitamin K1 epoxide

Spirodilactone

Geranylhydroquinone

2-Phytyl-1,4-naphthoquinone

delta-Tocopherol

beta-Tocopherol

alpha-Tocotrienol

beta-Tocotrienol

gamma-Tocotrienol

delta-Tocotrienol

1,4-Dihydroxy-2-naphthoyl-CoA

2-Methyl-6-phytylquinol

2,3-Dimethyl-5-phytylquinol

2-Succinyl-5-enolpyruvyl-6-hydroxy-3-cyclohexene-1-carboxylate

Plastoquinol-9

Futalosine

Dehypoxanthine futalosine

Cyclic dehypoxanthine futalosine

1,4-Dihydroxy-6-naphthoate

Shikonin

2-Polyprenyl-6-hydroxyphenol

2-Polyprenyl-6-methoxyphenol

3,4-Dihydroxy-5-polyprenylbenzoate

3-Methoxy-4-hydroxy-5-polyprenylbenzoate

2-Methyl-6-solanyl-1,4-benzoquinol

Geranyl-hydroxybenzoate

3''-Hydroxy-geranylhydroquinone

Deoxyshikonin

Dihydroechinofuran

Dihydroshikonofuran

Demethylmenaquinol

2-Methoxy-6-all-trans-polyprenyl-1,4-benzoquinol

6-Methoxy-3-methyl-2-all-trans-polyprenyl-1,4-benzoquinol

2,3-Epoxymenaquinone

6-Geranylgeranyl-2-methylbenzene-1,4-diol

6-Geranylgeranyl-2,3-dimethylbenzene-1,4-diol

3-[(1-Carboxyvinyl)oxy]benzoate

6-Amino-6-deoxyfutalosine

Demethylphylloquinol

3-Demethylubiquinol

2-Carboxy-1,4-naphthoquinone

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

Related
pathway

Oxidative phosphorylation

Phenylalanine, tyrosine and tryptophan biosynthesis

Terpenoid backbone biosynthesis

Phenylpropanoid biosynthesis

KO pathway

LinkDB

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