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evolution
plants have extensively diversified their arsenal of labdane-related diterpenoids (LRDs), in part via gene duplication and neo-functionalization of the ancestral ent-kaurene synthase (KS) required for gibberellin metabolism. Ricinus communis contains 4 RcKSL isozymes, molecular phylogenetic analysis indicates that RcKSL1 is significantly more closely related to dicotyl ent-kaurene synthases (KSs), while the other three, RcKSL2-4, cluster separately. RcKSL2-4 are in close proximity to each other, within a region of 65 kb, with RcKSL2 and 4 occurring as a tandem gene pair. RcKSL1 is the only isozyme to react with ent-CPP producing small amounts of ent-kaurene, and is referred to as RcKS1. Both RcKSL2 and RcKSL3 also are selectively reacting with ent-CPP with RcKSL2 producing primarily ent-trachylobane (70%) as well as smaller amounts of ent-kaurene (30%), and RcKSL3 producing ent-sandaracopimaradiene (94%) (EC 4.2.3.29) along with small amounts of ent-labdatriene (3%) and ent-pimaradiene (3%). RcKSL4 seems to be inactive, with no products evident from any substrate, but upon synthesis of a codon-optimized gene for the corrected aa sequence and functional analysis, RcKSL4 selectively reacts with ent-CPP and produces largely ent-beyerene (95%) along with very small amounts of ent-atiserene (4%) and ent-kaurene (1%). The enzymes belong to the terpene synthase family
evolution
PpCPS/KS is a multiproduct enzyme. It is one of the evolutionary earliest occurring plant diterpene synthases. Thus, PpCPS/KS may have been a multiproduct platform for later evolved diterpene synthases in plants
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
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
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
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
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
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
evolution
the enzyme is a class I bacterial diterpene cyclase
evolution
the enzyme is a class I diterpene cyclase
evolution
the enzyme is a class I diterpene cyclase
evolution
the enzyme is a class I diterpene synthase
evolution
the enzyme is a monofunctional class I diTPS
evolution
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the enzyme is a class I bacterial diterpene cyclase
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evolution
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the enzyme is a class I diterpene cyclase
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malfunction
CPS/KS disruption mutant lines have defect in protonemal development. The differentiation of chloronemata to caulonemata is suppressed in the CPS/KS knockout mutants
malfunction
CPS/KS disruption mutant lines have defect in protonemal development. The differentiation of chloronemata to caulonemata is suppressed in the CPS/KS knockout mutants
malfunction
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CPS/KS disruption mutant lines have defect in protonemal development. The differentiation of chloronemata to caulonemata iss suppressed in the CPS/KS knockout mutants
malfunction
caulonemal differentiation in a Physcomitrella patens mutant with a disrupted bifunctional ent-copalyl diphosphate synthase/ent-kaurene synthase (PpCPS/KS) gene is suppressed under red light, and is recovered by application of ent-kaurene and ent-kaurenoic acid. Although avoidance of the blue light source is not observed in the ent-kaurene deficient mutant protonemata, chloronemal growth toward a blue-light source in the mutant is suppressed by application of ent-kaurenoic acid, and the growth is rescued to that in the wild type
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
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
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
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
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
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
metabolism
class I bacterial diterpene cyclase, ent-kaurene synthase (BjKS) catalyzes the cyclization of ent-copalyl diphosphate (ent-CPP), which is produced by the separate (class II) enzyme, ent-copalyl diphosphate synthase (ent-CPPS, EC 5.5.1.13) from geranylgeranyl diphosphate, to ent-kaurene
metabolism
gibberellins (GAs) are ubiquitous diterpenoids in higher plants, whereas some higher plants produce unique species-specific diterpenoids. In gibberellins biosynthesis, ent-kaurene synthase and ent-kaurene oxidase are key players which catalyze early step(s) of the cyclization and oxidation reactions
metabolism
the enzyme catalyzes a step in the gibberellin biosynthetic pathway. The tanshinone biosynthetic pathway is uniquely initiated by a sequential pair of cyclization reactions catalyzed by SmCPS1 and SmKSL1 to produce abietane miltiradiene. Enzyme SmCPSent catalyzes the cyclization of geranylgeranyl diphosphate to ent-copalyl diphosphate (ent-CPP), which is converted to ent-kaurene by ent-kaurene synthase, SmKS. ent-Kaurene oxidase (SmKO) then catalyzes the three-step oxidation of ent-kaurene to ent-kaurenoic acid
metabolism
the enzyme is involved in gibberellin biosynthesis
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)
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)
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)
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)
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)
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)
metabolism
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class I bacterial diterpene cyclase, ent-kaurene synthase (BjKS) catalyzes the cyclization of ent-copalyl diphosphate (ent-CPP), which is produced by the separate (class II) enzyme, ent-copalyl diphosphate synthase (ent-CPPS, EC 5.5.1.13) from geranylgeranyl diphosphate, to ent-kaurene
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physiological function
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enzyme overexpression results in elevated gibberellic acid production
physiological function
copalyl diphosphate/kaurene synthase from the moss Physcomitrella patens (PpCPS/KS) is a bifunctional diterpene synthase and catalyses the formation of at least four diterpenes, including ent-beyerene, ent-sandaracopimaradiene, ent-kaur-16-ene, and 16-hydroxy-ent-kaurene
physiological function
ent-copalyl diphosphate (ent-CPP) is produced by the separate (class II) enzyme, ent-copalyl diphosphate synthase (ent-CPPS, EC 5.5.1.13), from geranylgeranyl diphosphate. The ent-kaur-16-ene synthase then catalyzes the cyclization of ent-copalyl diphosphate (ent-CPP) to ent-kaurene
physiological function
enzyme SdKS catalyzes a cyclization reaction from ent-copalyl diphosphate to ent-kaurene and is a key enzyme in the gibberellins biosynthesis
physiological function
geranylgeranyl diphosphate (GGPP) is an essential precursor in the biosynthesis of several diterpenes including ent-kaurene via formation of ent-copalyl diphosphate. Effect of isoprenoid precursors on ent-copalyl diphosphate and ent-kaurene production, ent-kaurene is quantified using GC-MS analysis
physiological function
plants have extensively diversified their arsenal of labdane-related diterpenoids (LRDs), in part via gene duplication and neo-functionalization of the ancestral ent-kaurene synthase (KS) required for gibberellin metabolism
physiological function
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the enzyme is involved in defense mechanisms in rice roots
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
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
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
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
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
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
physiological function
the moss Physcomitrella patens possesses parts of the gibberellins biosynthetic pathway, from geranylgeranyl diphosphate to ent-kaurenoic acid, but no gibberellins are found in this species. Derivatives of ent-kaurenoic acid, not gibberellins, might act as endogenous developmental regulators. Blue light regulates ent-kaurene biosynthesis and avoidance response to protonemal growth. When protonemata of the wild-type plants are incubated under blue light, the chloronemal filaments grow in the opposite direction to the light source. Regulators derived from ent-kaurenoic acid are strongly involved not only in the growth regulation of caulonemal differentiation under red light, but also in the light avoidance response of chloronemal growth under blue light. In particular, growth under blue light is regulated via the PpCPS/KS gene
physiological function
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ent-copalyl diphosphate (ent-CPP) is produced by the separate (class II) enzyme, ent-copalyl diphosphate synthase (ent-CPPS, EC 5.5.1.13), from geranylgeranyl diphosphate. The ent-kaur-16-ene synthase then catalyzes the cyclization of ent-copalyl diphosphate (ent-CPP) to ent-kaurene
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additional information
the enzyme amino acid sequence contains a DDFFD motif but lacks the DxDD motif, indicating that SmKS is a plant KS protein with monofunctional class I diTPS activity
additional information
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the enzyme amino acid sequence contains a DDFFD motif but lacks the DxDD motif, indicating that SmKS is a plant KS protein with monofunctional class I diTPS activity
additional information
the enzyme contains the highly conserved DDXXD sequence
additional information
the hydroxyl group of the Thr638 side chain enables occasional addition of water
additional information
the hydroxyl group of the Thr664 side chain enables occasional addition of water
additional information
the production of manoyl oxide proceeds from a substrate wherein oxygen is already present in the form of a hydroxyl group added during bicyclization of the general diterpenoid precursor (E,E,E)-geranylgeranyl diphosphate (GGPP) to 8alpha-hydroxy-copalyl diphosphate catalysed by recombinant Arabidopsis thaliana ent-copalyl diphosphate synthase mutant H263A, EC 5.5.1.13. 8alpha-Hydroxy-copalyl diphosphate is then converted to ent-13-epi-manoyl oxide by the modified ent-kaurene synthase function of enzyme FfCPS/KS mutant H212A
additional information
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the production of manoyl oxide proceeds from a substrate wherein oxygen is already present in the form of a hydroxyl group added during bicyclization of the general diterpenoid precursor (E,E,E)-geranylgeranyl diphosphate (GGPP) to 8alpha-hydroxy-copalyl diphosphate catalysed by recombinant Arabidopsis thaliana ent-copalyl diphosphate synthase mutant H263A, EC 5.5.1.13. 8alpha-Hydroxy-copalyl diphosphate is then converted to ent-13-epi-manoyl oxide by the modified ent-kaurene synthase function of enzyme PpCPS/KS mutant H302A
additional information
the production of manoyl oxide proceeds from a substrate wherein oxygen is already present in the form of a hydroxyl group added during bicyclization of the general diterpenoid precursor (E,E,E)-geranylgeranyl diphosphate (GGPP) to 8alpha-hydroxy-copalyl diphosphate catalysed by recombinant Arabidopsis thaliana ent-copalyl diphosphate synthase mutant H263A, EC 5.5.1.13. 8alpha-Hydroxy-copalyl diphosphate is then converted to ent-13-epi-manoyl oxide by the modified ent-kaurene synthase function of enzyme PpCPS/KS mutant H302A
additional information
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the enzyme contains the highly conserved DDXXD sequence
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additional information
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the production of manoyl oxide proceeds from a substrate wherein oxygen is already present in the form of a hydroxyl group added during bicyclization of the general diterpenoid precursor (E,E,E)-geranylgeranyl diphosphate (GGPP) to 8alpha-hydroxy-copalyl diphosphate catalysed by recombinant Arabidopsis thaliana ent-copalyl diphosphate synthase mutant H263A, EC 5.5.1.13. 8alpha-Hydroxy-copalyl diphosphate is then converted to ent-13-epi-manoyl oxide by the modified ent-kaurene synthase function of enzyme FfCPS/KS mutant H212A
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