BRENDA - Enzyme Database show
show all sequences of 4.2.3.B18

Bisabolyl-derived sesquiterpenes from tobacco 5-epi-aristolochene synthase-catalyzed cyclization of (2Z,6E)-farnesyl diphosphate

Faraldos, J.A.; OMaille, P.E.; Dellas, N.; Noel, J.P.; Coates, R.M.; J. Am. Chem. Soc. 132, 4281-4289 (2010)

Data extracted from this reference:

KM Value [mM]
KM Value [mM]
KM Value Maximum [mM]
Substrate
Commentary
Organism
Structure
0.01403
-
(2Z,6E)-farnesyl diphosphate
pH 7.5, 22°C
Nicotiana tabacum
Natural Substrates/ Products (Substrates)
Natural Substrates
Organism
Commentary (Nat. Sub.)
Natural Products
Commentary (Nat. Pro.)
Organism (Nat. Pro.)
Reversibility
(2Z,6E)-farnesyl diphosphate
Nicotiana tabacum
formation of seven bisabolyl-derived sesquiterpenes through the intermediacy of a common (7R)-beta-bisabolyl cation, (+)-2-epiprezizaene (44%) is the major product, (-)-alpha-cedrene (21.5%), (R)-(-)-beta-curcumene (15.5%), alpha-acoradiene (3.9%), 4-epi-alpha-acoradiene (1.3%), and equal amounts of alpha-bisabolol (1.8%) and epi-alpha-bisabolol (1.8%). The enzyme may be able to exploit the low natural levels (3-14%) of (2Z,6E)-farnesyl diphosphate generated by farnesyl diphosphate synthases to produce a different array of sesquiterpenes in vivo. If the concentration of (2E,2E)-farnesyl diphosphate is depleted by its diversion into biosynthesis of phytosterols, farnesylated proteins, or diterpenes, the enzyme would be capable of utilizing (2Z,6E)-farnesyl diphosphate in its place
(-)-alpha-cedrene + diphosphate
-
-
?
Organism
Organism
Primary Accession No. (UniProt)
Commentary
Textmining
Nicotiana tabacum
-
recombinant enzyme
-
Substrates and Products (Substrate)
Substrates
Commentary Substrates
Literature (Substrates)
Organism
Products
Commentary (Products)
Literature (Products)
Organism (Products)
Reversibility
(2Z,6E)-farnesyl diphosphate
formation of seven bisabolyl-derived sesquiterpenes through the intermediacy of a common (7R)-beta-bisabolyl cation, (+)-2-epiprezizaene (44%) is the major product, (-)-alpha-cedrene (21.5%), (R)-(-)-beta-curcumene (15.5%), alpha-acoradiene (3.9%), 4-epi-alpha-acoradiene (1.3%), and equal amounts of alpha-bisabolol (1.8%) and epi-alpha-bisabolol (1.8%). The enzyme may be able to exploit the low natural levels (3-14%) of (2Z,6E)-farnesyl diphosphate generated by farnesyl diphosphate synthases to produce a different array of sesquiterpenes in vivo. If the concentration of (2E,2E)-farnesyl diphosphate is depleted by its diversion into biosynthesis of phytosterols, farnesylated proteins, or diterpenes, the enzyme would be capable of utilizing (2Z,6E)-farnesyl diphosphate in its place
704204
Nicotiana tabacum
(-)-alpha-cedrene + diphosphate
-
-
-
?
(2Z,6E)-farnesyl diphosphate
formation of seven bisabolyl-derived sesquiterpenes through the intermediacy of a common (7R)-beta-bisabolyl cation, (+)-2-epiprezizaene (44%) is the major product, (-)-alpha-cedrene (21.5%), (R)-(-)-beta-curcumene (15.5%), alpha-acoradiene (3.9%), 4-epi-alpha-acoradiene (1.3%), and equal amounts of alpha-bisabolol (1.8%) and epi-alpha-bisabolol (1.8%)
704204
Nicotiana tabacum
(-)-alpha-cedrene + diphosphate
-
-
-
?
Temperature Optimum [°C]
Temperature Optimum [°C]
Temperature Optimum Maximum [°C]
Commentary
Organism
22
-
assay at
Nicotiana tabacum
Turnover Number [1/s]
Turnover Number Minimum [1/s]
Turnover Number Maximum [1/s]
Substrate
Commentary
Organism
Structure
0.095
-
(2Z,6E)-farnesyl diphosphate
pH 7.5, 22°C
Nicotiana tabacum
pH Optimum
pH Optimum Minimum
pH Optimum Maximum
Commentary
Organism
7.5
-
assay at
Nicotiana tabacum
KM Value [mM] (protein specific)
KM Value [mM]
KM Value Maximum [mM]
Substrate
Commentary
Organism
Structure
0.01403
-
(2Z,6E)-farnesyl diphosphate
pH 7.5, 22°C
Nicotiana tabacum
Natural Substrates/ Products (Substrates) (protein specific)
Natural Substrates
Organism
Commentary (Nat. Sub.)
Natural Products
Commentary (Nat. Pro.)
Organism (Nat. Pro.)
Reversibility
(2Z,6E)-farnesyl diphosphate
Nicotiana tabacum
formation of seven bisabolyl-derived sesquiterpenes through the intermediacy of a common (7R)-beta-bisabolyl cation, (+)-2-epiprezizaene (44%) is the major product, (-)-alpha-cedrene (21.5%), (R)-(-)-beta-curcumene (15.5%), alpha-acoradiene (3.9%), 4-epi-alpha-acoradiene (1.3%), and equal amounts of alpha-bisabolol (1.8%) and epi-alpha-bisabolol (1.8%). The enzyme may be able to exploit the low natural levels (3-14%) of (2Z,6E)-farnesyl diphosphate generated by farnesyl diphosphate synthases to produce a different array of sesquiterpenes in vivo. If the concentration of (2E,2E)-farnesyl diphosphate is depleted by its diversion into biosynthesis of phytosterols, farnesylated proteins, or diterpenes, the enzyme would be capable of utilizing (2Z,6E)-farnesyl diphosphate in its place
(-)-alpha-cedrene + diphosphate
-
-
?
Substrates and Products (Substrate) (protein specific)
Substrates
Commentary Substrates
Literature (Substrates)
Organism
Products
Commentary (Products)
Literature (Products)
Organism (Products)
Reversibility
(2Z,6E)-farnesyl diphosphate
formation of seven bisabolyl-derived sesquiterpenes through the intermediacy of a common (7R)-beta-bisabolyl cation, (+)-2-epiprezizaene (44%) is the major product, (-)-alpha-cedrene (21.5%), (R)-(-)-beta-curcumene (15.5%), alpha-acoradiene (3.9%), 4-epi-alpha-acoradiene (1.3%), and equal amounts of alpha-bisabolol (1.8%) and epi-alpha-bisabolol (1.8%). The enzyme may be able to exploit the low natural levels (3-14%) of (2Z,6E)-farnesyl diphosphate generated by farnesyl diphosphate synthases to produce a different array of sesquiterpenes in vivo. If the concentration of (2E,2E)-farnesyl diphosphate is depleted by its diversion into biosynthesis of phytosterols, farnesylated proteins, or diterpenes, the enzyme would be capable of utilizing (2Z,6E)-farnesyl diphosphate in its place
704204
Nicotiana tabacum
(-)-alpha-cedrene + diphosphate
-
-
-
?
(2Z,6E)-farnesyl diphosphate
formation of seven bisabolyl-derived sesquiterpenes through the intermediacy of a common (7R)-beta-bisabolyl cation, (+)-2-epiprezizaene (44%) is the major product, (-)-alpha-cedrene (21.5%), (R)-(-)-beta-curcumene (15.5%), alpha-acoradiene (3.9%), 4-epi-alpha-acoradiene (1.3%), and equal amounts of alpha-bisabolol (1.8%) and epi-alpha-bisabolol (1.8%)
704204
Nicotiana tabacum
(-)-alpha-cedrene + diphosphate
-
-
-
?
Temperature Optimum [°C] (protein specific)
Temperature Optimum [°C]
Temperature Optimum Maximum [°C]
Commentary
Organism
22
-
assay at
Nicotiana tabacum
Turnover Number [1/s] (protein specific)
Turnover Number Minimum [1/s]
Turnover Number Maximum [1/s]
Substrate
Commentary
Organism
Structure
0.095
-
(2Z,6E)-farnesyl diphosphate
pH 7.5, 22°C
Nicotiana tabacum
pH Optimum (protein specific)
pH Optimum Minimum
pH Optimum Maximum
Commentary
Organism
7.5
-
assay at
Nicotiana tabacum
KCat/KM [mM/s]
kcat/KM Value [1/mMs-1]
kcat/KM Value Maximum [1/mMs-1]
Substrate
Commentary
Organism
Structure
6.77
-
(2Z,6E)-farnesyl diphosphate
pH 7.5, 22°C
Nicotiana tabacum
KCat/KM [mM/s] (protein specific)
KCat/KM Value [1/mMs-1]
KCat/KM Value Maximum [1/mMs-1]
Substrate
Commentary
Organism
Structure
6.77
-
(2Z,6E)-farnesyl diphosphate
pH 7.5, 22°C
Nicotiana tabacum
Other publictions for EC 4.2.3.B18
No.
1st author
Pub Med
title
organims
journal
volume
pages
year
Activating Compound
Application
Cloned(Commentary)
Crystallization (Commentary)
Engineering
General Stability
Inhibitors
KM Value [mM]
Localization
Metals/Ions
Molecular Weight [Da]
Natural Substrates/ Products (Substrates)
Organic Solvent Stability
Organism
Oxidation Stability
Posttranslational Modification
Purification (Commentary)
Reaction
Renatured (Commentary)
Source Tissue
Specific Activity [micromol/min/mg]
Storage Stability
Substrates and Products (Substrate)
Subunits
Temperature Optimum [°C]
Temperature Range [°C]
Temperature Stability [°C]
Turnover Number [1/s]
pH Optimum
pH Range
pH Stability
Cofactor
Ki Value [mM]
pI Value
IC50 Value
Activating Compound (protein specific)
Application (protein specific)
Cloned(Commentary) (protein specific)
Cofactor (protein specific)
Crystallization (Commentary) (protein specific)
Engineering (protein specific)
General Stability (protein specific)
IC50 Value (protein specific)
Inhibitors (protein specific)
Ki Value [mM] (protein specific)
KM Value [mM] (protein specific)
Localization (protein specific)
Metals/Ions (protein specific)
Molecular Weight [Da] (protein specific)
Natural Substrates/ Products (Substrates) (protein specific)
Organic Solvent Stability (protein specific)
Oxidation Stability (protein specific)
Posttranslational Modification (protein specific)
Purification (Commentary) (protein specific)
Renatured (Commentary) (protein specific)
Source Tissue (protein specific)
Specific Activity [micromol/min/mg] (protein specific)
Storage Stability (protein specific)
Substrates and Products (Substrate) (protein specific)
Subunits (protein specific)
Temperature Optimum [°C] (protein specific)
Temperature Range [°C] (protein specific)
Temperature Stability [°C] (protein specific)
Turnover Number [1/s] (protein specific)
pH Optimum (protein specific)
pH Range (protein specific)
pH Stability (protein specific)
pI Value (protein specific)
Expression
General Information
General Information (protein specific)
Expression (protein specific)
KCat/KM [mM/s]
KCat/KM [mM/s] (protein specific)
701441
Noel
Structural elucidation of ciso ...
Nicotiana tabacum
ACS Chem. Biol.
5
377-392
2010
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704204
Faraldos
Bisabolyl-derived sesquiterpen ...
Nicotiana tabacum
J. Am. Chem. Soc.
132
4281-4289
2010
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