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Literature summary extracted from

  • Jia, M.; Peters, R.J.
    Extending a single residue switch for abbreviating catalysis in plant ent-kaurene synthases (2016), Front. Plant Sci., 7, 1765 .
    View publication on PubMedView publication on EuropePMC

Cloned(Commentary)

EC Number Cloned (Comment) Organism
4.2.3.19 expressed in Escherichia coli OverExpress C41 cells Physcomitrium patens
4.2.3.19 expressed in Escherichia coli OverExpress C41 cells Arabidopsis thaliana
4.2.3.19 expressed in Escherichia coli OverExpress C41 cells Selaginella moellendorffii
4.2.3.19 expressed in Escherichia coli OverExpress C41 cells Oryza sativa Japonica Group
4.2.3.19 expressed in Escherichia coli OverExpress C41 cells Picea glauca
4.2.3.19 expressed in Escherichia coli OverExpress C41 cells Marchantia polymorpha subsp. ruderalis
4.2.3.19 sequence comparisons, recombinant expression of wild-type and mutant enzymes in Escherichia coli strain C41(DE3) Physcomitrium patens
4.2.3.19 sequence comparisons, recombinant expression of wild-type and mutant enzymes in Escherichia coli strain C41(DE3) Arabidopsis thaliana
4.2.3.19 sequence comparisons, recombinant expression of wild-type and mutant enzymes in Escherichia coli strain C41(DE3) Oryza sativa Japonica Group
4.2.3.19 sequence comparisons, recombinant expression of wild-type and mutant enzymes in Escherichia coli strain C41(DE3) Picea glauca
4.2.3.19 sequence comparisons, recombinant expression of wild-type and mutant enzymes in Escherichia coli strain C41(DE3) Marchantia polymorpha subsp. ruderalis
4.2.3.19 sequence comparisons, recombinant expression of wild-type enzyme in Escherichia coli strain C41(DE3) Selaginella moellendorffii
4.2.3.30 gene OsKSL5j, sequence comparisons and phylogenetic analysis and tree Oryza sativa Japonica Group

Protein Variants

EC Number Protein Variants Comment Organism
4.2.3.19 I368A the mutant produces ent-pimara-8(14),15-diene, ent-kaur-16-ene, 8alpha-hydroxy-ent-pimara-15-ene, and ent-pimara-7,15-diene from ent-copalyl diphosphate Arabidopsis thaliana
4.2.3.19 I368S the mutant produces ent-pimara-8(14),15-diene and 8alpha-hydroxy-ent-pimara-15-ene from ent-copalyl diphosphate Arabidopsis thaliana
4.2.3.19 I368T the mutant produces ent-pimara-8(14),15-diene from ent-copalyl diphosphate Arabidopsis thaliana
4.2.3.19 I368V the mutant produces ent-kaur-16-ene from ent-copalyl diphosphate Arabidopsis thaliana
4.2.3.19 I619A site-directed mutagenesis, the mutant shows altered product spectrum compared to the wild-type enzyme Picea glauca
4.2.3.19 I638A site-directed mutagenesis, the mutant shows altered product spectrum compared to the wild-type enzyme, the mutant produces a mixture of four products, pedominantly ent-pimara-8(14),15-diene, and a small amount of the double bond isomer ent-pimara-7,15-diene, and variable amounts of ent-kaur-16-ene, as well as substantial amounts of 8a-hydroxy-ent-pimar-15-ene Arabidopsis thaliana
4.2.3.19 I638S site-directed mutagenesis, the mutant shows altered product spectrum compared to the wild-type enzyme, the mutant produces a mixture of four products, pedominantly ent-pimara-8(14),15-diene, and a small amount of the double bond isomer ent-pimara-7,15-diene, and variable amounts of ent-kaur-16-ene, as well as substantial amounts of 8a-hydroxy-ent-pimar-15-ene Arabidopsis thaliana
4.2.3.19 I638T site-directed mutagenesis, the mutant shows altered product spectrum compared to the wild-type enzyme, the mutant produces a mixture of four products, pedominantly ent-pimara-8(14),15-diene, and small amounts of the double bond isomer ent-pimara-7,15-diene and 8a-hydroxy-ent-pimar-15-ene, and variable amounts of ent-kaur-16-ene Arabidopsis thaliana
4.2.3.19 I638V site-directed mutagenesis, the mutant shows unaltered product spectrum compared to the wild-type enzyme and produces just ent-kaur-16-ene Arabidopsis thaliana
4.2.3.19 I645T site-directed mutagenesis, the mutant shows altered product spectrum compared to the wild-type enzyme, the mutant produces almost entirely ent-pimara-8(14),15-diene, reaction of EC 4.2.3.30 Marchantia polymorpha subsp. ruderalis
4.2.3.19 I645T the mutant produces ent-pimara-8(14),15-diene from ent-copalyl diphosphate Marchantia polymorpha subsp. ruderalis
4.2.3.19 I664A site-directed mutagenesis, the mutant shows altered product spectrum compared to the wild-type enzyme, the mutant produces significant amounts of 8alpha-hydroxy-ent-pimara-15-ene generated by addition of water prior to deprotonation, it also produces ent-copalol, the dephosphorylated derivative of ent-copalyl diphosphate Oryza sativa Japonica Group
4.2.3.19 I664S site-directed mutagenesis, the mutant shows altered product spectrum compared to the wild-type enzyme, the mutant produces significant amounts of 8alpha-hydroxy-ent-pimara-15-ene generated by addition of water prior to deprotonation, it also produces ent-copalol, the dephosphorylated derivative of ent-copalyl diphosphate Oryza sativa Japonica Group
4.2.3.19 I664T site-directed mutagenesis, the mutant shows altered product spectrum compared to the wild-type enzyme, the mutant produces high amounts of ent-pimara-8(14),15-diene, it also produces ent-copalol, the dephosphorylated derivative of ent-copalyl diphosphate Oryza sativa Japonica Group
4.2.3.19 I664V site-directed mutagenesis, the mutant shows altered product spectrum compared to the wild-type enzyme, the mutant produces ent-isokaurene and ent-copalol, the dephosphorylated derivative of ent-copalyl diphosphate Oryza sativa Japonica Group
4.2.3.19 I741T site-directed mutagenesis, the mutant shows altered product spectrum compared to the wild-type enzyme, the mutant produces almost entirely ent-pimara-8(14),15-diene, reaction of EC 4.2.3.30 Physcomitrium patens
4.2.3.19 I741T the mutant produces ent-pimara-8(14),15-diene from ent-copalyl diphosphate Physcomitrium patens

Localization

EC Number Localization Comment Organism GeneOntology No. Textmining
4.2.3.19 chloroplast
-
 Physcomitrium patens 9507
-
4.2.3.19 chloroplast
-
 Arabidopsis thaliana 9507
-
4.2.3.19 chloroplast
-
 Selaginella moellendorffii 9507
-
4.2.3.19 chloroplast
-
 Oryza sativa Japonica Group 9507
-
4.2.3.19 chloroplast
-
 Picea glauca 9507
-
4.2.3.19 chloroplast
-
 Marchantia polymorpha subsp. ruderalis 9507
-

Natural Substrates/ Products (Substrates)

EC Number Natural Substrates Organism Comment (Nat. Sub.) Natural Products Comment (Nat. Pro.) Rev. Reac.
4.2.3.19 ent-copalyl diphosphate Physcomitrium patens
-
 ent-kaur-16-ene + 6alpha-hydroxy-ent-kaurane + diphosphate
-
 ?
4.2.3.19 ent-copalyl diphosphate Physcomitrium patens
-
 ent-kaur-16-ene + diphosphate
-
 ?
4.2.3.19 ent-copalyl diphosphate Arabidopsis thaliana
-
 ent-kaur-16-ene + diphosphate
-
 ?
4.2.3.19 ent-copalyl diphosphate Selaginella moellendorffii
-
 ent-kaur-16-ene + diphosphate
-
 ?
4.2.3.19 ent-copalyl diphosphate Oryza sativa Japonica Group
-
 ent-kaur-16-ene + diphosphate
-
 ?
4.2.3.19 ent-copalyl diphosphate Picea glauca
-
 ent-kaur-16-ene + diphosphate
-
 ?
4.2.3.19 ent-copalyl diphosphate Marchantia polymorpha subsp. ruderalis
-
 ent-kaur-16-ene + diphosphate
-
 ?
4.2.3.30 ent-copalyl diphosphate Marchantia polymorpha activity of the mutant I645T of kaurene synthase, EC 4.2.3.19 ent-pimara-8(14),15-diene + diphosphate
-
 ?
4.2.3.30 ent-copalyl diphosphate Oryza sativa Japonica Group activity of the mutant I664T of kaurene synthase, EC 4.2.3.19 ent-pimara-8(14),15-diene + diphosphate
-
 ?
4.2.3.30 ent-copalyl diphosphate Physcomitrium patens activity of the mutant I741T of kaurene synthase, EC 4.2.3.19 ent-pimara-8(14),15-diene + diphosphate
-
 ?

Organism

EC Number Organism UniProt Comment Textmining
4.2.3.19 Arabidopsis thaliana Q9SAK2
-
-
4.2.3.19 Marchantia polymorpha subsp. ruderalis A0A176VPW0
-
-
4.2.3.19 Oryza sativa Japonica Group Q0JA82
-
-
4.2.3.19 Physcomitrium patens A5A8G0
-
-
4.2.3.19 Picea glauca D2XEB3
-
-
4.2.3.19 Selaginella moellendorffii A0A077JGG8
-
-
4.2.3.30 Marchantia polymorpha
-
-
-
4.2.3.30 Oryza sativa Japonica Group
-
-
-
4.2.3.30 Physcomitrium patens
-
-
-

Purification (Commentary)

EC Number Purification (Comment) Organism
4.2.3.19 recombinant wild-type and mutant enzymes from Escherichia coli strain C41(DE3) Physcomitrium patens
4.2.3.19 recombinant wild-type and mutant enzymes from Escherichia coli strain C41(DE3) Arabidopsis thaliana
4.2.3.19 recombinant wild-type and mutant enzymes from Escherichia coli strain C41(DE3) Oryza sativa Japonica Group
4.2.3.19 recombinant wild-type and mutant enzymes from Escherichia coli strain C41(DE3) Picea glauca
4.2.3.19 recombinant wild-type and mutant enzymes from Escherichia coli strain C41(DE3) Marchantia polymorpha subsp. ruderalis
4.2.3.19 recombinant wild-type enzyme from Escherichia coli strain C41(DE3) Selaginella moellendorffii

Reaction

EC Number Reaction Comment Organism Reaction ID
4.2.3.19 ent-copalyl diphosphate = ent-kaurene + diphosphate cyclization mechanism catalyzed by KSs and the Ile mutants, via ent-pimar-15-en-8-yl, ent-beyeran-16-yl, and ent-kauran-16-yl intermediates, detailed overview Physcomitrium patens
a
4.2.3.19 ent-copalyl diphosphate = ent-kaurene + diphosphate cyclization mechanism catalyzed by KSs and the Ile mutants, via ent-pimar-15-en-8-yl, ent-beyeran-16-yl, and ent-kauran-16-yl intermediates, detailed overview Arabidopsis thaliana
a
4.2.3.19 ent-copalyl diphosphate = ent-kaurene + diphosphate cyclization mechanism catalyzed by KSs and the Ile mutants, via ent-pimar-15-en-8-yl, ent-beyeran-16-yl, and ent-kauran-16-yl intermediates, detailed overview Selaginella moellendorffii
a
4.2.3.19 ent-copalyl diphosphate = ent-kaurene + diphosphate cyclization mechanism catalyzed by KSs and the Ile mutants, via ent-pimar-15-en-8-yl, ent-beyeran-16-yl, and ent-kauran-16-yl intermediates, detailed overview Oryza sativa Japonica Group
a
4.2.3.19 ent-copalyl diphosphate = ent-kaurene + diphosphate cyclization mechanism catalyzed by KSs and the Ile mutants, via ent-pimar-15-en-8-yl, ent-beyeran-16-yl, and ent-kauran-16-yl intermediates, detailed overview Picea glauca
a
4.2.3.19 ent-copalyl diphosphate = ent-kaurene + diphosphate cyclization mechanism catalyzed by KSs and the Ile mutants, via ent-pimar-15-en-8-yl, ent-beyeran-16-yl, and ent-kauran-16-yl intermediates, detailed overview Marchantia polymorpha subsp. ruderalis
a

Substrates and Products (Substrate)

EC Number Substrates Comment Substrates Organism Products Comment (Products) Rev. Reac.
4.2.3.19 ent-copalyl diphosphate enzyme OsKSL5i, via the ent-kauran-16-yl intermediate, overview Oryza sativa Japonica Group ent-isokaur-15-ene + diphosphate
-
 ?
4.2.3.19 ent-copalyl diphosphate
-
 Physcomitrium patens ent-kaur-16-ene + 6alpha-hydroxy-ent-kaurane + diphosphate
-
 ?
4.2.3.19 ent-copalyl diphosphate
-
 Physcomitrium patens ent-kaur-16-ene + diphosphate
-
 ?
4.2.3.19 ent-copalyl diphosphate
-
 Arabidopsis thaliana ent-kaur-16-ene + diphosphate
-
 ?
4.2.3.19 ent-copalyl diphosphate
-
 Selaginella moellendorffii ent-kaur-16-ene + diphosphate
-
 ?
4.2.3.19 ent-copalyl diphosphate
-
 Oryza sativa Japonica Group ent-kaur-16-ene + diphosphate
-
 ?
4.2.3.19 ent-copalyl diphosphate
-
 Picea glauca ent-kaur-16-ene + diphosphate
-
 ?
4.2.3.19 ent-copalyl diphosphate
-
 Marchantia polymorpha subsp. ruderalis ent-kaur-16-ene + diphosphate
-
 ?
4.2.3.19 ent-copalyl diphosphate almost exclusive production of ent-kaurene and 16alpha-hydroxy-ent-kaur-ene by the wild-type PpCPS/KS enzyme, while mutant I741T shows ent-pimara-8(14),15-diene synthase activity, EC 4.2.3.30 Physcomitrium patens ent-kaur-16-ene + diphosphate
-
 ?
4.2.3.19 ent-copalyl diphosphate almost exclusive production of ent-kaurene by the wild-type MpKS enzyme, while mutant I645T shows ent-pimara-8(14),15-diene synthase activity, EC 4.2.3.30 Marchantia polymorpha subsp. ruderalis ent-kaur-16-ene + diphosphate
-
 ?
4.2.3.19 ent-copalyl diphosphate + H2O almost exclusive production of ent-kaurene and 16alpha-hydroxy-ent-kaur-ene by the wild-type PpCPS/KS enzyme, while mutant I741T shows ent-pimara-8(14),15-diene synthase activity, EC 4.2.3.30 Physcomitrium patens 16alpha-hydroxy-ent-kaur-ene + diphosphate
-
 ?
4.2.3.19 additional information GC-MS analysis of products, overview Physcomitrium patens ?
-
 ?
4.2.3.19 additional information GC-MS analysis of products, overview Arabidopsis thaliana ?
-
 ?
4.2.3.19 additional information GC-MS analysis of products, overview Selaginella moellendorffii ?
-
 ?
4.2.3.19 additional information GC-MS analysis of products, overview Oryza sativa Japonica Group ?
-
 ?
4.2.3.19 additional information GC-MS analysis of products, overview Picea glauca ?
-
 ?
4.2.3.19 additional information GC-MS analysis of products, overview Marchantia polymorpha subsp. ruderalis ?
-
 ?
4.2.3.30 ent-copalyl diphosphate activity of the mutant I645T of kaurene synthase, EC 4.2.3.19 Marchantia polymorpha ent-pimara-8(14),15-diene + diphosphate
-
 ?
4.2.3.30 ent-copalyl diphosphate activity of the mutant I664T of kaurene synthase, EC 4.2.3.19 Oryza sativa Japonica Group ent-pimara-8(14),15-diene + diphosphate
-
 ?
4.2.3.30 ent-copalyl diphosphate activity of the mutant I741T of kaurene synthase, EC 4.2.3.19 Physcomitrium patens ent-pimara-8(14),15-diene + diphosphate
-
 ?
4.2.3.30 additional information the mutant MpKS:I645T produces almost entirely ent-pimara-8(14),15-diene Marchantia polymorpha ?
-
 ?
4.2.3.30 additional information the mutant PpCPS/KS:I741T produces almost entirely ent-pimara-8(14),15-diene Physcomitrium patens ?
-
 ?
4.2.3.30 additional information the OsKSL5 mutant I664A produces almost exclusively ent-pimara-8(14),15-diene, it also produces low amounts of ent-copalol, the dephosphorylated derivative of ent-copalyl diphosphate Oryza sativa Japonica Group ?
-
 ?

Synonyms

EC Number Synonyms Comment Organism
4.2.3.19 (-)-ent-kaurene synthase
-
 Picea glauca
4.2.3.19 AtKS
-
 Arabidopsis thaliana
4.2.3.19 bifunctional CPS/KS
-
 Physcomitrium patens
4.2.3.19 bifunctional CPS/KS
-
 Selaginella moellendorffii
4.2.3.19 ent-kaur-16-ene synthase
-
 Arabidopsis thaliana
4.2.3.19 ent-kaur-16-ene synthase
-
 Oryza sativa Japonica Group
4.2.3.19 KS1A UniProt Oryza sativa Japonica Group
4.2.3.19 KSL5
-
 Oryza sativa Japonica Group
4.2.3.19 MpKS
-
 Marchantia polymorpha subsp. ruderalis
4.2.3.19 PgKS
-
 Picea glauca
4.2.3.19 PpCPS/KS
-
 Physcomitrium patens
4.2.3.19 SmKS
-
 Selaginella moellendorffii

Temperature Optimum [°C]

EC Number Temperature Optimum [°C] Temperature Optimum Maximum [°C] Comment Organism
4.2.3.19 37
-
 assay at Physcomitrium patens
4.2.3.19 37
-
 assay at Arabidopsis thaliana
4.2.3.19 37
-
 assay at Selaginella moellendorffii
4.2.3.19 37
-
 assay at Oryza sativa Japonica Group
4.2.3.19 37
-
 assay at Picea glauca
4.2.3.19 37
-
 assay at Marchantia polymorpha subsp. ruderalis

pH Optimum

EC Number pH Optimum Minimum pH Optimum Maximum Comment Organism
4.2.3.19 7
-
 assay at Physcomitrium patens
4.2.3.19 7
-
 assay at Arabidopsis thaliana
4.2.3.19 7
-
 assay at Selaginella moellendorffii
4.2.3.19 7
-
 assay at Oryza sativa Japonica Group
4.2.3.19 7
-
 assay at Picea glauca
4.2.3.19 7
-
 assay at Marchantia polymorpha subsp. ruderalis

General Information

EC Number General Information Comment Organism
4.2.3.19 evolution production of ent-kaurene as a precursor for important signaling molecules such as the gibberellins seems to have arisen early in plant evolution, with corresponding cyclase(s) present in all land plants (i.e., embryophyta). The relevant enzymes seem to represent fusion of the class II diterpene cyclase that produces the intermediate ent-copalyl diphosphate (ent-CPP) and the subsequently acting class I diterpene synthase that produces ent-kaurene, although the bifunctionality of the ancestral gene is only retained in certain early diverging plants, with gene duplication and sub-functionalization leading to distinct ent-CPP synthases and ent-kaurene synthases (KSs) generally observed Physcomitrium patens
4.2.3.19 evolution production of ent-kaurene as a precursor for important signaling molecules such as the gibberellins seems to have arisen early in plant evolution, with corresponding cyclase(s) present in all land plants (i.e., embryophyta). The relevant enzymes seem to represent fusion of the class II diterpene cyclase that produces the intermediate ent-copalyl diphosphate (ent-CPP) and the subsequently acting class I diterpene synthase that produces ent-kaurene, although the bifunctionality of the ancestral gene is only retained in certain early diverging plants, with gene duplication and sub-functionalization leading to distinct ent-CPP synthases and ent-kaurene synthases (KSs) generally observed Arabidopsis thaliana
4.2.3.19 evolution production of ent-kaurene as a precursor for important signaling molecules such as the gibberellins seems to have arisen early in plant evolution, with corresponding cyclase(s) present in all land plants (i.e., embryophyta). The relevant enzymes seem to represent fusion of the class II diterpene cyclase that produces the intermediate ent-copalyl diphosphate (ent-CPP) and the subsequently acting class I diterpene synthase that produces ent-kaurene, although the bifunctionality of the ancestral gene is only retained in certain early diverging plants, with gene duplication and sub-functionalization leading to distinct ent-CPP synthases and ent-kaurene synthases (KSs) generally observed Selaginella moellendorffii
4.2.3.19 evolution production of ent-kaurene as a precursor for important signaling molecules such as the gibberellins seems to have arisen early in plant evolution, with corresponding cyclase(s) present in all land plants (i.e., embryophyta). The relevant enzymes seem to represent fusion of the class II diterpene cyclase that produces the intermediate ent-copalyl diphosphate (ent-CPP) and the subsequently acting class I diterpene synthase that produces ent-kaurene, although the bifunctionality of the ancestral gene is only retained in certain early diverging plants, with gene duplication and sub-functionalization leading to distinct ent-CPP synthases and ent-kaurene synthases (KSs) generally observed Oryza sativa Japonica Group
4.2.3.19 evolution production of ent-kaurene as a precursor for important signaling molecules such as the gibberellins seems to have arisen early in plant evolution, with corresponding cyclase(s) present in all land plants (i.e., embryophyta). The relevant enzymes seem to represent fusion of the class II diterpene cyclase that produces the intermediate ent-copalyl diphosphate (ent-CPP) and the subsequently acting class I diterpene synthase that produces ent-kaurene, although the bifunctionality of the ancestral gene is only retained in certain early diverging plants, with gene duplication and sub-functionalization leading to distinct ent-CPP synthases and ent-kaurene synthases (KSs) generally observed Picea glauca
4.2.3.19 evolution production of ent-kaurene as a precursor for important signaling molecules such as the gibberellins seems to have arisen early in plant evolution, with corresponding cyclase(s) present in all land plants (i.e., embryophyta). The relevant enzymes seem to represent fusion of the class II diterpene cyclase that produces the intermediate ent-copalyl diphosphate (ent-CPP) and the subsequently acting class I diterpene synthase that produces ent-kaurene, although the bifunctionality of the ancestral gene is only retained in certain early diverging plants, with gene duplication and sub-functionalization leading to distinct ent-CPP synthases and ent-kaurene synthases (KSs) generally observed Marchantia polymorpha subsp. ruderalis
4.2.3.19 malfunction substitution of threonine for a conserved isoleucine has been shown to short-circuit the complex bicyclization and rearrangement reaction catalyzed by ent-kaurene synthases (KSs) after initial cyclization, leading to predominant production of ent-pimaradiene, at least in KSs from angiosperms. This effect extends to KSs from earlier diverging plants (i.e., bryophytes), including a bifunctional/KS. A dramatic effect of this single residue switch on product outcome to electrostatic stabilization of the ent-pimarenyl carbocation intermediate formed upon initial cyclization by the hydroxyl introduced by threonine substitution is paralleled by similar effects from substitution of alanine Physcomitrium patens
4.2.3.19 malfunction substitution of threonine for a conserved isoleucine has been shown to short-circuit the complex bicyclization and rearrangement reaction catalyzed by ent-kaurene synthases (KSs) after initial cyclization, leading to predominant production of ent-pimaradiene, at least in KSs from angiosperms. This effect extends to KSs from earlier diverging plants (i.e., bryophytes), including a bifunctional/KS. A dramatic effect of this single residue switch on product outcome to electrostatic stabilization of the ent-pimarenyl carbocation intermediate formed upon initial cyclization by the hydroxyl introduced by threonine substitution is paralleled by similar effects from substitution of alanine Arabidopsis thaliana
4.2.3.19 malfunction substitution of threonine for a conserved isoleucine has been shown to short-circuit the complex bicyclization and rearrangement reaction catalyzed by ent-kaurene synthases (KSs) after initial cyclization, leading to predominant production of ent-pimaradiene, at least in KSs from angiosperms. This effect extends to KSs from earlier diverging plants (i.e., bryophytes), including a bifunctional/KS. A dramatic effect of this single residue switch on product outcome to electrostatic stabilization of the ent-pimarenyl carbocation intermediate formed upon initial cyclization by the hydroxyl introduced by threonine substitution is paralleled by similar effects from substitution of alanine Selaginella moellendorffii
4.2.3.19 malfunction substitution of threonine for a conserved isoleucine has been shown to short-circuit the complex bicyclization and rearrangement reaction catalyzed by ent-kaurene synthases (KSs) after initial cyclization, leading to predominant production of ent-pimaradiene, at least in KSs from angiosperms. This effect extends to KSs from earlier diverging plants (i.e., bryophytes), including a bifunctional/KS. A dramatic effect of this single residue switch on product outcome to electrostatic stabilization of the ent-pimarenyl carbocation intermediate formed upon initial cyclization by the hydroxyl introduced by threonine substitution is paralleled by similar effects from substitution of alanine Oryza sativa Japonica Group
4.2.3.19 malfunction substitution of threonine for a conserved isoleucine has been shown to short-circuit the complex bicyclization and rearrangement reaction catalyzed by ent-kaurene synthases (KSs) after initial cyclization, leading to predominant production of ent-pimaradiene, at least in KSs from angiosperms. This effect extends to KSs from earlier diverging plants (i.e., bryophytes), including a bifunctional/KS. A dramatic effect of this single residue switch on product outcome to electrostatic stabilization of the ent-pimarenyl carbocation intermediate formed upon initial cyclization by the hydroxyl introduced by threonine substitution is paralleled by similar effects from substitution of alanine Picea glauca
4.2.3.19 malfunction substitution of threonine for a conserved isoleucine has been shown to short-circuit the complex bicyclization and rearrangement reaction catalyzed by ent-kaurene synthases (KSs) after initial cyclization, leading to predominant production of ent-pimaradiene, at least in KSs from angiosperms. This effect extends to KSs from earlier diverging plants (i.e., bryophytes), including a bifunctional/KS. A dramatic effect of this single residue switch on product outcome to electrostatic stabilization of the ent-pimarenyl carbocation intermediate formed upon initial cyclization by the hydroxyl introduced by threonine substitution is paralleled by similar effects from substitution of alanine Marchantia polymorpha subsp. ruderalis
4.2.3.19 metabolism the enzyme produces the diterpene ent-kaur-16-ene, which in vascular plants (i.e., tracheophytes) serves as an intermediate in biosynthesis of the gibberellin phytohormones. Production of ent-kaur-16-ene from the general diterpenoid precursor (E,E,E)-geranylgeranyl diphosphate (GGPP) proceeds via two distinct bicyclization reactions. The first is catalyzed by copalyl diphosphate synthases (CPSs, EC 5.5.1.13) that are representative of class II diterpene cyclases and produce ent-copalyl diphosphate. This is then subsequently further cyclized and rearranged by ent-kaurene synthases (KSs) Physcomitrium patens
4.2.3.19 metabolism the enzyme produces the diterpene ent-kaur-16-ene, which in vascular plants (i.e., tracheophytes) serves as an intermediate in biosynthesis of the gibberellin phytohormones. Production of ent-kaur-16-ene from the general diterpenoid precursor (E,E,E)-geranylgeranyl diphosphate (GGPP) proceeds via two distinct bicyclization reactions. The first is catalyzed by copalyl diphosphate synthases (CPSs, EC 5.5.1.13) that are representative of class II diterpene cyclases and produce ent-copalyl diphosphate. This is then subsequently further cyclized and rearranged by ent-kaurene synthases (KSs) Arabidopsis thaliana
4.2.3.19 metabolism the enzyme produces the diterpene ent-kaur-16-ene, which in vascular plants (i.e., tracheophytes) serves as an intermediate in biosynthesis of the gibberellin phytohormones. Production of ent-kaur-16-ene from the general diterpenoid precursor (E,E,E)-geranylgeranyl diphosphate (GGPP) proceeds via two distinct bicyclization reactions. The first is catalyzed by copalyl diphosphate synthases (CPSs, EC 5.5.1.13) that are representative of class II diterpene cyclases and produce ent-copalyl diphosphate. This is then subsequently further cyclized and rearranged by ent-kaurene synthases (KSs) Selaginella moellendorffii
4.2.3.19 metabolism the enzyme produces the diterpene ent-kaur-16-ene, which in vascular plants (i.e., tracheophytes) serves as an intermediate in biosynthesis of the gibberellin phytohormones. Production of ent-kaur-16-ene from the general diterpenoid precursor (E,E,E)-geranylgeranyl diphosphate (GGPP) proceeds via two distinct bicyclization reactions. The first is catalyzed by copalyl diphosphate synthases (CPSs, EC 5.5.1.13) that are representative of class II diterpene cyclases and produce ent-copalyl diphosphate. This is then subsequently further cyclized and rearranged by ent-kaurene synthases (KSs) Oryza sativa Japonica Group
4.2.3.19 metabolism the enzyme produces the diterpene ent-kaur-16-ene, which in vascular plants (i.e., tracheophytes) serves as an intermediate in biosynthesis of the gibberellin phytohormones. Production of ent-kaur-16-ene from the general diterpenoid precursor (E,E,E)-geranylgeranyl diphosphate (GGPP) proceeds via two distinct bicyclization reactions. The first is catalyzed by copalyl diphosphate synthases (CPSs, EC 5.5.1.13) that are representative of class II diterpene cyclases and produce ent-copalyl diphosphate. This is then subsequently further cyclized and rearranged by ent-kaurene synthases (KSs) Picea glauca
4.2.3.19 metabolism the enzyme produces the diterpene ent-kaur-16-ene, which in vascular plants (i.e., tracheophytes) serves as an intermediate in biosynthesis of the gibberellin phytohormones. Production of ent-kaur-16-ene from the general diterpenoid precursor (E,E,E)-geranylgeranyl diphosphate (GGPP) proceeds via two distinct bicyclization reactions. The first is catalyzed by copalyl diphosphate synthases (CPSs, EC 5.5.1.13) that are representative of class II diterpene cyclases and produce ent-copalyl diphosphate. This is then subsequently further cyclized and rearranged by ent-kaurene synthases (KSs) Marchantia polymorpha subsp. ruderalis
4.2.3.19 additional information the hydroxyl group of the Thr638 side chain enables occasional addition of water Arabidopsis thaliana
4.2.3.19 additional information the hydroxyl group of the Thr664 side chain enables occasional addition of water Oryza sativa Japonica Group
4.2.3.19 physiological function the enzyme produces the diterpene ent-kaur-16-ene, which in vascular plants (i.e., tracheophytes) serves as an intermediate in biosynthesis of the gibberellin phytohormones Physcomitrium patens
4.2.3.19 physiological function the enzyme produces the diterpene ent-kaur-16-ene, which in vascular plants (i.e., tracheophytes) serves as an intermediate in biosynthesis of the gibberellin phytohormones Arabidopsis thaliana
4.2.3.19 physiological function the enzyme produces the diterpene ent-kaur-16-ene, which in vascular plants (i.e., tracheophytes) serves as an intermediate in biosynthesis of the gibberellin phytohormones Selaginella moellendorffii
4.2.3.19 physiological function the enzyme produces the diterpene ent-kaur-16-ene, which in vascular plants (i.e., tracheophytes) serves as an intermediate in biosynthesis of the gibberellin phytohormones Oryza sativa Japonica Group
4.2.3.19 physiological function the enzyme produces the diterpene ent-kaur-16-ene, which in vascular plants (i.e., tracheophytes) serves as an intermediate in biosynthesis of the gibberellin phytohormones Picea glauca
4.2.3.19 physiological function the enzyme produces the diterpene ent-kaur-16-ene, which in vascular plants (i.e., tracheophytes) serves as an intermediate in biosynthesis of the gibberellin phytohormones Marchantia polymorpha subsp. ruderalis