5.5.1.12: copalyl diphosphate synthase
This is an abbreviated version!
For detailed information about copalyl diphosphate synthase, go to the full flat file.
Word Map on EC 5.5.1.12
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5.5.1.12
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geranylgeranyl
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salvia
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gibberellin
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diterpenoids
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miltiorrhiza
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tanshinone
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ent-kaurene
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miltiradiene
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kaurene
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carbocation
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+-copalyl
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protonation-initiated
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ent-copalyl
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abietane-type
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cryptotanshinone
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ditpss
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ferruginol
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e,e,e-geranylgeranyl
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manoyl
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dihydrotanshinone
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abietane
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labdane
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phaeosphaeria
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norditerpenoids
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steviol
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labdane-related
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abietic
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synthesis
- 5.5.1.12
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geranylgeranyl
- salvia
- gibberellin
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diterpenoids
- miltiorrhiza
- tanshinone
- ent-kaurene
- miltiradiene
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kaurene
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carbocation
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+-copalyl
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protonation-initiated
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ent-copalyl
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abietane-type
- cryptotanshinone
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ditpss
- ferruginol
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e,e,e-geranylgeranyl
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manoyl
- dihydrotanshinone
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abietane
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labdane
- phaeosphaeria
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norditerpenoids
- steviol
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labdane-related
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abietic
- synthesis
Reaction
Synonyms
(+)-copalyl diphosphate synthase, (+)-CPS, (-)-abietadiene synthase, abietadiene cyclase, abietadiene synthase, AGAS, BDTC, bifunctional diterpene cyclase, bifunctional LAS-type diTPS, class II diterpene synthase, class II diTPS, CPP synthase, CPS, CPS1, CPS2, CPS3, cyclase, abietadiene, diTPS-ISO, ISO, isopimaradiene synthase-type diTPS, LAS, LAS1, levopimaradiene/abietadiene synthase-type diTPS, More, MvCPS3, PaLAS, RoCPS1, SmCPS, SmCPS1, SmCPS2, TPS-LAS, TPS2
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General Information on EC 5.5.1.12 - copalyl diphosphate synthase
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GENERAL INFORMATION 
ORGANISM
UNIPROT
COMMENTARY 
LITERATURE
evolution
malfunction
changing two adjacent residues that seem to serve as the catalytic base in the normal CPP synthase from Salvia miltiorrhiza (SmCPS) to the residues found in the closely related perigrinol diphosphate synthase from Marrubium vulgare (MvPPS), which produces a partially rearranged and hydroxylated product derived from the distinct syn stereoisomer of labdaenyl intermediate, alters the product outcome, cf. EC 5.5.1.14. Specifically, the relevant SmCPS:H315N/T316V double mutant produces terpentedienyl diphosphate, which is derived from complete substituent rearrangement of syn rather than normal labdaenyl intermediate. Alteration of the residues that normally serve as the catalytic base can impact stereocontrol
metabolism
physiological function
the chloroplastidic bifunctional diterpene synthase, isopimara-7,15-diene synthase (diTPS-ISO) from Picea abies and a cytosolic multifunctional cytochrome P450 (CYP720B4, UniProt ID E5FA70) from Picea sitchensis, which is associated to the endoplasmic reticulum. The diterpene synthase diTPS-ISO converts geranylgeranyl diphosphate (GGPP) to the tricyclic diterpene isopimara-7,15-diene (isopimaradiene)
additional information
evolution
the enzyme belongs to the class II diterpene synthases, phylogenetic tree, diterpene biosynthesis in gymnosperms, overview
evolution
the enzyme belongs to the class II diterpene synthases, phylogenetic tree, diterpene biosynthesis in gymnosperms, overview
evolution
diterpene synthases transcriptome analysis of Marrubium vulgare leaves, overview. CPS3 is a class II diterpene synthase, phylogenetic analysis
evolution
the bifunctional enzyme belongs to the class I and II diterpene synthases
metabolism
bifunctional class I/II PcLAS1 and PbLAS1 enzymes can supply (+)-copalyl diphosphate for the Monofunctional class I enzymes
metabolism
bifunctional diterpene cyclases are involved in hormone and defense compound biosyntheses in bryophytes and gymnosperms, respectively
metabolism
several stereoisomers of copalyl diphosphate (CDP) are found, among which the most common is ent-CDP, the precursor of gibberellins. Other isomers are syn-CDP and normal-CDP, the latter being utilized for the biosynthesis of diterpene resin acids in Gymnosperms and abietane-type tanshinones in Salvia miltiorrhiza. The second step of the cyclization is initiated through the formation of a carbocation upon ionization of the diphosphate linkage of CDP. This is catalyzed by class I terpene synthases which can transform CDP into a variety of polycyclic diterpenoids. By analogy to other labdane-type diterpenoids, the biosynthesis of the diterpene precursor of the carnosic acid pathway in rosemary proceeds in two sequential steps catalyzed by two distinct enzymes. The first is a class II TPS enzyme, CPS1, that yields normal CDP, which then is converted to miltiradiene by a KSL enzyme, miltiradiene synthase, EC 4.2.3.131, which apears in two isoforms, RoKSL1 and RoKSL2, in Rosmarinus officinalis. Hypothetical biosynthetic pathway of carnosic acid and carnosol produced in Rosmarinus officinalis, overview
metabolism
the bifunctional diterpene synthase, isopimara-7, 15-diene synthase (diTPS-ISO) and a multifunctional cytochrome P450, CYP720B4 perform the biosynthesis of isopimaric acid. The diterpene synthase converts geranylgeranyl diphosphate (GGPP) to the tricyclic diterpene isopimara-7,15-diene (isopimaradiene) via formation of (+)-copalyl diphosphate. In three subsequent oxygenation reactions, the endoplasmic reticulum-associated enzyme CYP720B4 catalyzes the conversion of isopimaradiene into isopimaric acid, pathway overview
additional information
enzyme structure by two-dimensional and three-dimensional NMR
additional information
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enzyme structure by two-dimensional and three-dimensional NMR
additional information
class II diterpene cyclases (DTCs) utilize a general acid-base catalyzed cyclo-isomerization reaction to produce various stereoisomers of the eponymous labdaenyl carbocation intermediate, which can then undergo rearrangement and/or the addition of water prior to terminating deprotonation. Identification of the pair of residues that cooperatively serves as the catalytic base in the DTCs producing ent-copalyl diphosphate (CPP) required for gibberellin phytohormone biosynthesis in all vascular plants, overview
additional information
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class II diterpene cyclases (DTCs) utilize a general acid-base catalyzed cyclo-isomerization reaction to produce various stereoisomers of the eponymous labdaenyl carbocation intermediate, which can then undergo rearrangement and/or the addition of water prior to terminating deprotonation. Identification of the pair of residues that cooperatively serves as the catalytic base in the DTCs producing ent-copalyl diphosphate (CPP) required for gibberellin phytohormone biosynthesis in all vascular plants, overview
additional information
enzyme CPS3 contains a DIDD functional motif
additional information
A0A0A7AN31
metabolomic profiling, and homology modeling and molecular docking
additional information
metabolomic profiling, and homology modeling and molecular docking
additional information
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metabolomic profiling, and homology modeling and molecular docking
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