MetaCyc Pathway: ent-kaurene biosynthesis I
Inferred from experiment

Enzyme View:

Pathway diagram: ent-kaurene biosynthesis I

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.

Superclasses: BiosynthesisHormones BiosynthesisPlant Hormones BiosynthesisGibberellins and Gibberellin Precursors Biosynthesis
BiosynthesisSecondary Metabolites BiosynthesisTerpenoids BiosynthesisDiterpenoids BiosynthesisGibberellins and Gibberellin Precursors Biosynthesis

Some taxa known to possess this pathway include : Arabidopsis thaliana col, Cucurbita maxima, Fusarium fujikuroi, Oryza sativa

Expected Taxonomic Range: Fungi, Viridiplantae

General Background

The biosynthesis of ent-kaurene represents the first committed step in the biosynthesis of gibberellins in the terpenoid biosynthesis. As diterpenoids, gibberellins are synthesized from the geranylgeranyl diphosphate (GGPP), which is also an essential precursor in the biosynthesis of several isoprenoids necessary for plant growth and development such as carotenoids, prenyl quinines, chlorophylls and formation of geranygeranylated proteins. GGPP synthase catalyzes the condensation of IPP (originating, in plants, from the plastidic methylerythritol phosphate pathway I) with an allylic prenyl diphosphate FPP to give GGPP. Cyclization of the linear GGPP to the tetracyclic ent-kaurene occurs in two steps; first GGPP is converted to the bicyclic compound ent-copalyl diphosphate by an enzyme called copalyl diphosphate synthase (CPS) which is then converted to ent-kaurene by an ent-kaurene synthase (KS). In Arabidopsis, these enzymes have been shown to be localized in plastids. In the fungi Fusarium fujikuroi and Phaeosphaeria spp. CPS and KS activities reside in the same protein, albeit in separate catalytic sites [Kawaide97, Kawaide00, Toyomasu00]. In plants, however, both activities are carried by two separate enzymes. In Arabidopsis CPS transcripts are present in much lower quantities than those of KS transcripts, indicating that CPS may act as a bottle-neck regulator functioning as a branch point in terpenoid biosynthesis, and committing to the synthesis of ent-kaurenoids and GAs [Sponsel04].

Superpathways: superpathway of gibberellin biosynthesis, superpathway of gibberellin GA12 biosynthesis, kauralexin biosynthesis

Unification Links: AraCyc:PWY-5032


Kawaide00: Kawaide H, Sassa T, Kamiya Y (2000). "Functional analysis of the two interacting cyclase domains in ent-kaurene synthase from the fungus Phaeosphaeria sp. L487 and a comparison with cyclases from higher plants." J Biol Chem 275(4);2276-80. PMID: 10644675

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

Sponsel04: Sponsel V.M., Hedden P. (2004). "Gibberellin biosynthesis and inactivation." Plant Hormones. Biosynthesis, Signal transduction, Action! Kluwer Academic Publishers, Ed. P.J. Davies.

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

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

Fleet03: Fleet CM, Yamaguchi S, Hanada A, Kawaide H, David CJ, Kamiya Y, Sun TP (2003). "Overexpression of AtCPS and AtKS in Arabidopsis confers increased ent-kaurene production but no increase in bioactive gibberellins." Plant Physiol 132(2);830-9. PMID: 12805613

Harris05: Harris LJ, Saparno A, Johnston A, Prisic S, Xu M, Allard S, Kathiresan A, Ouellet T, Peters RJ (2005). "The maize An2 gene is induced by Fusarium attack and encodes an ent-copalyl diphosphate synthase." Plant Mol Biol 59(6);881-94. PMID: 16307364

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

Helliwell01: Helliwell CA, Sullivan JA, Mould RM, Gray JC, Peacock WJ, Dennis ES (2001). "A plastid envelope location of Arabidopsis ent-kaurene oxidase links the plastid and endoplasmic reticulum steps of the gibberellin biosynthesis pathway." Plant J 28(2);201-8. PMID: 11722763

Karp04: Karp PD (2004). "Call for an enzyme genomics initiative." Genome Biol 5(8);401. PMID: 15287973

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

Prisic04: Prisic S, Xu M, Wilderman PR, Peters RJ (2004). "Rice contains two disparate ent-copalyl diphosphate synthases with distinct metabolic functions." Plant Physiol 136(4);4228-36. PMID: 15542489

Sakamoto04a: Sakamoto T, Miura K, Itoh H, Tatsumi T, Ueguchi-Tanaka M, Ishiyama K, Kobayashi M, Agrawal GK, Takeda S, Abe K, Miyao A, Hirochika H, Kitano H, Ashikari M, Matsuoka M (2004). "An overview of gibberellin metabolism enzyme genes and their related mutants in rice." Plant Physiol 134(4);1642-53. PMID: 15075394

Schmelz11: Schmelz EA, Kaplan F, Huffaker A, Dafoe NJ, Vaughan MM, Ni X, Rocca JR, Alborn HT, Teal PE (2011). "Identity, regulation, and activity of inducible diterpenoid phytoalexins in maize." Proc Natl Acad Sci U S A 108(13);5455-60. PMID: 21402917

Sun94: Sun TP, Kamiya Y (1994). "The Arabidopsis GA1 locus encodes the cyclase ent-kaurene synthetase A of gibberellin biosynthesis." Plant Cell 1994;6(10);1509-18. PMID: 7994182

Yamaguchi96: Yamaguchi S, Saito T, Abe H, Yamane H, Murofushi N, Kamiya Y (1996). "Molecular cloning and characterization of a cDNA encoding the gibberellin biosynthetic enzyme ent-kaurene synthase B from pumpkin (Cucurbita maxima L.)." Plant J 10(2);203-13. PMID: 8771778

Yamaguchi98: Yamaguchi S, Sun T, Kawaide H, Kamiya Y (1998). "The GA2 locus of Arabidopsis thaliana encodes ent-kaurene synthase of gibberellin biosynthesis." Plant Physiol 1998;116(4);1271-8. PMID: 9536043

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Please cite the following article in publications resulting from the use of MetaCyc: Caspi et al, Nucleic Acids Research 42:D459-D471 2014
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