KEGG   PATHWAY: avl00900
Entry
avl00900                    Pathway                                
Name
Terpenoid backbone biosynthesis - Azotobacter vinelandii CA
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
avl00900  Terpenoid backbone biosynthesis
avl00900

Module
avl_M00096  C5 isoprenoid biosynthesis, non-mevalonate pathway [PATH:avl00900]
avl_M00364  C10-C20 isoprenoid biosynthesis, bacteria [PATH:avl00900]
Other DBs
GO: 0009240 0016091
Organism
Azotobacter vinelandii CA [GN:avl]
Gene
AvCA_07870  dxs-1; 1-deoxy-D-xylulose-5-phosphate synthase [KO:K01662] [EC:2.2.1.7]
AvCA_20590  dxs-2; 1-deoxy-D-xylulose-5-phosphate synthase [KO:K01662] [EC:2.2.1.7]
AvCA_38930  dxr; 1-deoxy-D-xylulose 5-phosphate reductoisomerase [KO:K00099] [EC:1.1.1.267]
AvCA_38770  ispD; 2-C-methyl-D-erythritol 4-phosphate cytidylyltransferase [KO:K00991] [EC:2.7.7.60]
AvCA_41510  ipk; 4-diphosphocytidyl-2-C-methyl-D-erythritol kinase [KO:K00919] [EC:2.7.1.148]
AvCA_38730  ispF; 2-C-methyl-D-erythritol 2,4-cyclodiphosphate synthase [KO:K01770] [EC:4.6.1.12]
AvCA_40290  ispG; 4-hydroxy-3-methylbut-2-en-1-yl diphosphate synthase [KO:K03526] [EC:1.17.7.1 1.17.7.3]
AvCA_11810  ispH; 4-hydroxy-3-methylbut-2-enyl diphosphate reductase [KO:K03527] [EC:1.17.7.4]
AvCA_17360  Acetyl-CoA C-acyltransferase [KO:K00626] [EC:2.3.1.9]
AvCA_14260  aat1; beta-ketothiolase [KO:K00626] [EC:2.3.1.9]
AvCA_16380  acetoacetyl-CoA thiolase [KO:K00626] [EC:2.3.1.9]
AvCA_07370  Thiolase [KO:K00626] [EC:2.3.1.9]
AvCA_22240  acetyl-CoA acetyltransferase [KO:K00626] [EC:2.3.1.9]
AvCA_51590  bktA; acetyl-CoA acetyltransferase [KO:K00626] [EC:2.3.1.9]
AvCA_23640  phbA; acetyl-CoA acetyltransferase [KO:K00626] [EC:2.3.1.9]
AvCA_08040  ubiX; aromatic acid decarboxylase [KO:K03186] [EC:2.5.1.129]
AvCA_20640  idi; isopentenyl-diphosphate delta-isomerase, type 1 [KO:K01823] [EC:5.3.3.2]
AvCA_20600  ispA-2; geranyltranstransferase [KO:K13789] [EC:2.5.1.1 2.5.1.10 2.5.1.29]
AvCA_07880  ispA-1; geranyltranstransferase [KO:K13789] [EC:2.5.1.1 2.5.1.10 2.5.1.29]
AvCA_40810  gerC; Trans-hexaprenyltranstransferase [KO:K02523] [EC:2.5.1.90]
AvCA_38950  uppS; undecaprenyl diphosphate synthase [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 5-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
avl00010  Glycolysis / Gluconeogenesis
avl00130  Ubiquinone and other terpenoid-quinone biosynthesis
avl00270  Cysteine and methionine metabolism
avl00906  Carotenoid biosynthesis
avl00909  Sesquiterpenoid and triterpenoid biosynthesis
KO pathway
ko00900   
LinkDB

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