KEGG   PATHWAY: xbo00900
Entry
xbo00900                    Pathway                                
Name
Terpenoid backbone biosynthesis - Xenorhabdus bovienii SS-2004
Description
Terpenoids, also known as isoprenoids, are a large class of natural products consisting of isoprene (C5) units. There are two biosynthetic pathways, the mevalonate pathway [MD:M00095] and the non-mevalonate pathway or the MEP/DOXP pathway [MD:M00096], for the terpenoid building blocks: isopentenyl diphosphate (IPP) and dimethylallyl diphosphate (DMAPP). The action of prenyltransferases then generates higher-order building blocks: geranyl diphosphate (GPP), farsenyl diphosphate (FPP), and geranylgeranyl diphosphate (GGPP), which are the precursors of monoterpenoids (C10), sesquiterpenoids (C15), and diterpenoids (C20), respectively. Condensation of these building blocks gives rise to the precursors of sterols (C30) and carotenoids (C40). The MEP/DOXP pathway is absent in higher animals and fungi, but in green plants the MEP/DOXP and mevalonate pathways co-exist in separate cellular compartments. The MEP/DOXP pathway, operating in the plastids, is responsible for the formation of essential oil monoterpenes and linalyl acetate, some sesquiterpenes, diterpenes, and carotenoids and phytol. The mevalonate pathway, operating in the cytosol, gives rise to triterpenes, sterols, and most sesquiterpenes.
Class
Metabolism; Metabolism of terpenoids and polyketides
Pathway map
xbo00900  Terpenoid backbone biosynthesis
xbo00900

Other DBs
GO: 0009240 0016091
Organism
Xenorhabdus bovienii SS-2004 [GN:xbo]
Gene
XBJ1_1659  dxs; 1-deoxy-D-xylulose 5-phosphate synthase; flavoprotein, thiamin-binding [KO:K01662] [EC:2.2.1.7]
XBJ1_0593  dxr; 1-deoxy-D-xylulose 5-phosphate reductoisomerase [KO:K00099] [EC:1.1.1.267]
XBJ1_3603  ispD; 4-diphosphocytidyl-2C-methyl-D-erythritol synthase [KO:K00991] [EC:2.7.7.60]
XBJ1_2199  ispE; 4-diphosphocytidyl-2C-methyl-D-erythritol kinase [KO:K00919] [EC:2.7.1.148]
XBJ1_3602  ispF; 2C-methyl-D-erythritol 2,4-cyclodiphosphate synthase [KO:K01770] [EC:4.6.1.12]
XBJ1_3007  ispG; 1-hydroxy-2-methyl-2-(E)-butenyl 4-diphosphate synthase [KO:K03526] [EC:1.17.7.1 1.17.7.3]
XBJ1_1723  ispH; 1-hydroxy-2-methyl-2-(E)-butenyl 4-diphosphate reductase, 4Fe-4S protein [KO:K03527] [EC:1.17.7.4]
XBJ1_2958  ubiX; 3-octaprenyl-4-hydroxybenzoate carboxy-lyase [KO:K03186] [EC:2.5.1.129]
XBJ1_1658  ispA; geranyltranstransferase (=farnesyldiphosphate synthase) [KO:K00795] [EC:2.5.1.1 2.5.1.10]
XBJ1_0353  ispB; octaprenyl diphosphate synthase [KO:K02523] [EC:2.5.1.90]
XBJ1_0594  ispU; undecaprenyl pyrophosphate synthetase (di-trans,poly-cis-decaprenylcistransferase) [KO:K00806] [EC:2.5.1.31]
Compound
C00022  Pyruvate
C00024  Acetyl-CoA
C00118  D-Glyceraldehyde 3-phosphate
C00129  Isopentenyl diphosphate
C00235  Dimethylallyl diphosphate
C00332  Acetoacetyl-CoA
C00341  Geranyl diphosphate
C00353  Geranylgeranyl diphosphate
C00356  (S)-3-Hydroxy-3-methylglutaryl-CoA
C00418  (R)-Mevalonate
C00448  trans,trans-Farnesyl diphosphate
C01107  (R)-5-Phosphomevalonate
C01126  (2E,6E)-Farnesol
C01143  (R)-5-Diphosphomevalonate
C01230  all-trans-Hexaprenyl diphosphate
C02321  cis-1,4-Polyisoprene
C03461  2-trans,6-trans-Farnesal
C04145  all-trans-Nonaprenyl diphosphate
C04146  all-trans-Octaprenyl diphosphate
C04216  all-trans-Heptaprenyl diphosphate
C04506  Protein C-terminal S-farnesyl-L-cysteine
C04574  di-trans,poly-cis-Undecaprenyl diphosphate
C04748  Protein C-terminal S-farnesyl-L-cysteine methyl ester
C05427  Phytyl diphosphate
C05859  ditrans,polycis-Polyprenyl diphosphate
C06081  Polyprenol
C11434  2-C-Methyl-D-erythritol 4-phosphate
C11435  4-(Cytidine 5'-diphospho)-2-C-methyl-D-erythritol
C11436  2-Phospho-4-(cytidine 5'-diphospho)-2-C-methyl-D-erythritol
C11437  1-Deoxy-D-xylulose 5-phosphate
C11453  2-C-Methyl-D-erythritol 2,4-cyclodiphosphate
C11811  1-Hydroxy-2-methyl-2-butenyl 4-diphosphate
C16521  Isoprene
C16826  2-cis,6-trans-Farnesyl diphosphate
C17432  all-trans-Decaprenyl diphosphate
C18321  trans,octacis-Decaprenyl diphosphate
C19691  Farnesylcysteine
C19760  2-cis,6-cis-Farnesyl diphosphate
C19852  tritrans,heptacis-Undecaprenyl diphosphate
C19853  trans,polycis-Polyprenyl diphosphate
C20120  S-Farnesyl protein
C20121  trans,trans-Farnesyl phosphate
C20345  Isopentenyl phosphate
C20847  (R)-Mevalonate 3-phosphate
C20848  (R)-Mevalonate 3,5-bisphosphate
C22453  trans-Anhydromevalonate phosphate
Reference
  Authors
Lange BM, Ghassemian M.
  Title
Genome organization in Arabidopsis thaliana: a survey for genes involved in isoprenoid and chlorophyll metabolism.
  Journal
Plant Mol Biol 51:925-48 (2003)
DOI:10.1023/A:1023005504702
Reference
  Authors
Saiki R, Nagata A, Kainou T, Matsuda H, Kawamukai M
  Title
Characterization of solanesyl and decaprenyl diphosphate synthases in mice and humans.
  Journal
FEBS J 272:5606-22 (2005)
DOI:10.1111/j.1742-4658.2005.04956.x
Reference
PMID:9858571
  Authors
Sato M, Sato K, Nishikawa S, Hirata A, Kato J, Nakano A
  Title
The yeast RER2 gene, identified by endoplasmic reticulum protein localization mutations, encodes cis-prenyltransferase, a key enzyme in dolichol synthesis.
  Journal
Mol Cell Biol 19:471-83 (1999)
DOI:10.1128/MCB.19.1.471
Reference
  Authors
Vannice JC, Skaff DA, Keightley A, Addo JK, Wyckoff GJ, Miziorko HM
  Title
Identification in Haloferax volcanii of phosphomevalonate decarboxylase and isopentenyl phosphate kinase as catalysts of the terminal enzyme reactions in an  archaeal alternate mevalonate pathway.
  Journal
J Bacteriol 196:1055-63 (2014)
DOI:10.1128/JB.01230-13
Related
pathway
xbo00010  Glycolysis / Gluconeogenesis
xbo00130  Ubiquinone and other terpenoid-quinone biosynthesis
xbo00270  Cysteine and methionine metabolism
KO pathway
ko00900   

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