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MetaCyc Pathway: ent -kaurene biosynthesis II

Enzyme View:

This view shows enzymes only for those organisms listed below, in the list of taxa known to possess the pathway. If an enzyme name is shown in bold, there is experimental evidence for this enzymatic activity.

Synonyms: ent -kaurene biosynthesis in bryophyta, ent -kaurene biosynthesis in fungi

Superclasses: Biosynthesis Hormones Biosynthesis Plant Hormones Biosynthesis Gibberellins and Gibberellin Precursors Biosynthesis
Biosynthesis Secondary Metabolites Biosynthesis Terpenoids Biosynthesis Diterpenoids Biosynthesis Gibberellins and Gibberellin Precursors Biosynthesis

Some taxa known to possess this pathway include ? : Diaporthe amygdali , Fusarium fujikuroi , Phaeosphaeria sp. L487 , Physcomitrella patens Inferred from experiment [Hayashi06]

Expected Taxonomic Range: Bryopsida , Opisthokonta

Summary:
ent -kaurene is an important hydrocarbon precursor of gibberelin biosynthesis. It is formed by the two step cyclization of geranylgeranyl diphosphate via copalyl diphosphate. These compunds are produced by a number of fungi, and have been isolated and characterized from Diaporthe amygdali [Toyomasu08], Fusarium fujikuroi [Tudzynski98], [Toyomasu00], as well as in higher plants (see ent-kaurene biosynthesis I). However the phyllogentic analysis of the gene clusters of the above pathway in different organisms shows that the enzymes have evolved in an interesting manner. In lower forms like fungi and moss the key enzyme is a bifunctional enzyme that cyclizes the geranylgeranyl diphosphate directly to the ent kaurene products [Hayashi06], in higher plants two distinct enzymes carry out the cyclization of geranylgeranyl diphosphate in a two step reaction [Kanno06]

Credits:
Created 20-Oct-2010 by Pujar A , Boyce Thompson Institute


References

Hayashi06: Hayashi K, Kawaide H, Notomi M, Sakigi Y, Matsuo A, Nozaki H (2006). "Identification and functional analysis of bifunctional ent-kaurene synthase from the moss Physcomitrella patens." FEBS Lett 580(26);6175-81. PMID: 17064690

Kanno06: Kanno Y, Otomo K, Kenmoku H, Mitsuhashi W, Yamane H, Oikawa H, Toshima H, Matsuoka M, Sassa T, Toyomasu T (2006). "Characterization of a rice gene family encoding type-A diterpene cyclases." Biosci Biotechnol Biochem 70(7);1702-10. PMID: 16861806

Toyomasu00: Toyomasu T, Kawaide H, Ishizaki A, Shinoda S, Otsuka M, Mitsuhashi W, Sassa T (2000). "Cloning of a full-length cDNA encoding ent-kaurene synthase from Gibberella fujikuroi: functional analysis of a bifunctional diterpene cyclase." Biosci Biotechnol Biochem 64(3);660-4. PMID: 10803977

Toyomasu08: Toyomasu T, Niida R, Kenmoku H, Kanno Y, Miura S, Nakano C, Shiono Y, Mitsuhashi W, Toshima H, Oikawa H, Hoshino T, Dairi T, Kato N, Sassa T (2008). "Identification of diterpene biosynthetic gene clusters and functional analysis of labdane-related diterpene cyclases in Phomopsis amygdali." Biosci Biotechnol Biochem 72(4);1038-47. PMID: 18391465

Tudzynski98: Tudzynski B, Kawaide H, Kamiya Y (1998). "Gibberellin biosynthesis in Gibberella fujikuroi: cloning and characterization of the copalyl diphosphate synthase gene." Curr Genet 34(3);234-40. PMID: 9745028

Other References Related to Enzymes, Genes, Subpathways, and Substrates of this Pathway

Cho04: Cho EM, Okada A, Kenmoku H, Otomo K, Toyomasu T, Mitsuhashi W, Sassa T, Yajima A, Yabuta G, Mori K, Oikawa H, Toshima H, Shibuya N, Nojiri H, Omori T, Nishiyama M, Yamane H (2004). "Molecular cloning and characterization of a cDNA encoding ent-cassa-12,15-diene synthase, a putative diterpenoid phytoalexin biosynthetic enzyme, from suspension-cultured rice cells treated with a chitin elicitor." Plant J 37(1);1-8. PMID: 14675427

Kawaide97: Kawaide H, Imai R, Sassa T, Kamiya Y (1997). "Ent-kaurene synthase from the fungus Phaeosphaeria sp. L487. cDNA isolation, characterization, and bacterial expression of a bifunctional diterpene cyclase in fungal gibberellin biosynthesis." J Biol Chem 272(35);21706-12. PMID: 9268298

Latendresse13: Latendresse M. (2013). "Computing Gibbs Free Energy of Compounds and Reactions in MetaCyc."

Nemoto04: Nemoto T, Cho EM, Okada A, Okada K, Otomo K, Kanno Y, Toyomasu T, Mitsuhashi W, Sassa T, Minami E, Shibuya N, Nishiyama M, Nojiri H, Yamane H (2004). "Stemar-13-ene synthase, a diterpene cyclase involved in the biosynthesis of the phytoalexin oryzalexin S in rice." FEBS Lett 571(1-3);182-6. PMID: 15280039

Otomo04: Otomo K, Kenmoku H, Oikawa H, Konig WA, Toshima H, Mitsuhashi W, Yamane H, Sassa T, Toyomasu T (2004). "Biological functions of ent- and syn-copalyl diphosphate synthases in rice: key enzymes for the branch point of gibberellin and phytoalexin biosynthesis." Plant J 39(6);886-93. PMID: 15341631


Report Errors or Provide Feedback
Please cite the following article in publications resulting from the use of MetaCyc: Caspi et al, Nucleic Acids Research 42:D459-D471 2014
Page generated by SRI International Pathway Tools version 18.5 on Sat Nov 22, 2014, biocyc14.