BRENDA - Enzyme Database
show all sequences of 1.1.1.324

Acyclic monoterpene primary alcohol:NADP+ oxidoreductase of Rauwolfia serpentina cells: the key enzyme in biosynthesis of monoterpene alcohols

Ikeda, H.; Esaki, N.; Nakai, S.; Hashimoto, K.; Uesato, S.; Soda, K.; Fujita, T.; J. Biochem. 109, 341-347 (1991)

Data extracted from this reference:

General Stability
General Stability
Organism
the enzyme rapidly and irreversibly loses its activity when 1 mM dithiothreitol and 20% glycerol v/v are omitted from the enzyme solution
Rauvolfia serpentina
Inhibitors
Inhibitors
Commentary
Organism
Structure
iridodial
-
Rauvolfia serpentina
isopulegol
-
Rauvolfia serpentina
menthol
competitive against 8-hydroxygeraniol
Rauvolfia serpentina
KM Value [mM]
KM Value [mM]
KM Value Maximum [mM]
Substrate
Commentary
Organism
Structure
additional information
-
additional information
steady-state kinetic studies show that the nerol dehydrogenation proceeds by an ordered Bi-Bi mechanism, NADP+ binds the enzyme first and then NADPH is the second product released from it, kinetic mechanism, overview
Rauvolfia serpentina
Metals/Ions
Metals/Ions
Commentary
Organism
Structure
additional information
the enzyme contains no Mo, Co, Cu, Fe, Mn, Mg, Ca, Se, Pt, and Au
Rauvolfia serpentina
Zn2+
the enzyme contains zinc ions
Rauvolfia serpentina
Molecular Weight [Da]
Molecular Weight [Da]
Molecular Weight Maximum [Da]
Commentary
Organism
44000
-
1 * 44000, SDS-PAGE
Rauvolfia serpentina
50000
-
native enzyme, gel filtration
Rauvolfia serpentina
Natural Substrates/ Products (Substrates)
Natural Substrates
Organism
Commentary (Nat. Sub.)
Natural Products
Commentary (Nat. Pro.)
Organism (Nat. Pro.)
Reversibility
(6E)-8-hydroxygeraniol + 2 NADP+
Rauvolfia serpentina
10-hydroxygeraniol undergoes a reversible dehydrogenation to produce 8-oxogeraniol or 8-hydroxygeranial, which are oxidized further to give 8-oxogeranial, the direct precursor of iridodial
(6E)-8-oxogeranial + 2 NADPH + 2 H+
-
-
r
additional information
Rauvolfia serpentina
various branched-chain allylic primary alcohols, such as nerol, geraniol, and 8-hydroxygeraniol, are substrates, but ethanol is inert. The enzyme is also active with farnesol, 3-methyl-2-buten1-ol, citronellol, 4-isopropylbenzyl alcohol, trans-2-heptenol, and trans-2-hexenol. The enzyme exclusively transfers the pro-R hydrogen of NADPH to neral. No activity with linalool, 2,6-dimethyl-octane, iridodial, 1-octanol, 1-heptanol, 1-pentanol, 3-methyl-3-buten-1-ol, trans-crotyl alcohol, isopulegol, and menthol
?
-
-
-
Organism
Organism
Primary Accession No. (UniProt)
Commentary
Textmining
Rauvolfia serpentina
-
-
-
Purification (Commentary)
Commentary
Organism
native enzyme to homogeneity by ammonium sulfate fractionation, hydrophobic interaction, anion exchange, and AF-Red dye affinity chromatography followed by gel filtration
Rauvolfia serpentina
Specific Activity [micromol/min/mg]
Specific Activity Minimum [µmol/min/mg]
Specific Activity Maximum [µmol/min/mg]
Commentary
Organism
2.7
-
purified enzyme, pH 9.0, 25°C
Rauvolfia serpentina
Storage Stability
Storage Stability
Organism
-20°C, purified enzyme, 20 mM Tris HCl, pH 8.0, 20% glycerol, 1 mM DTT, 6 months without loss of activity
Rauvolfia serpentina
Substrates and Products (Substrate)
Substrates
Commentary Substrates
Literature (Substrates)
Organism
Products
Commentary (Products)
Literature (Products)
Organism (Products)
Reversibility
(6E)-8-hydroxygeraniol + 2 NADP+
-
717741
Rauvolfia serpentina
(6E)-8-oxogeranial + 2 NADPH + 2 H+
-
-
-
r
(6E)-8-hydroxygeraniol + 2 NADP+
10-hydroxygeraniol undergoes a reversible dehydrogenation to produce 8-oxogeraniol or 8-hydroxygeranial, which are oxidized further to give 8-oxogeranial, the direct precursor of iridodial
717741
Rauvolfia serpentina
(6E)-8-oxogeranial + 2 NADPH + 2 H+
-
-
-
r
(6E)-8-hydroxynerol + 2 NADP+
-
717741
Rauvolfia serpentina
? + 2 NADPH + 2 H+
-
-
-
r
geraniol + 2 NADP+
-
717741
Rauvolfia serpentina
? + 2 NADPH + 2 H+
-
-
-
r
additional information
various branched-chain allylic primary alcohols, such as nerol, geraniol, and 8-hydroxygeraniol, are substrates, but ethanol is inert. The enzyme is also active with farnesol, 3-methyl-2-buten1-ol, citronellol, 4-isopropylbenzyl alcohol, trans-2-heptenol, and trans-2-hexenol. The enzyme exclusively transfers the pro-R hydrogen of NADPH to neral. No activity with linalool, 2,6-dimethyl-octane, iridodial, 1-octanol, 1-heptanol, 1-pentanol, 3-methyl-3-buten-1-ol, trans-crotyl alcohol, isopulegol, and menthol
717741
Rauvolfia serpentina
?
-
-
-
-
nerol + 2 NADP+
-
717741
Rauvolfia serpentina
? + 2 NADPH + 2 H+
-
-
-
r
Subunits
Subunits
Commentary
Organism
monomer
1 * 44000, SDS-PAGE
Rauvolfia serpentina
Temperature Optimum [°C]
Temperature Optimum [°C]
Temperature Optimum Maximum [°C]
Commentary
Organism
25
-
assay at
Rauvolfia serpentina
pH Optimum
pH Optimum Minimum
pH Optimum Maximum
Commentary
Organism
7
-
reverse reaction assay at
Rauvolfia serpentina
9
-
forward reaction assay at
Rauvolfia serpentina
Cofactor
Cofactor
Commentary
Organism
Structure
NADP+
the enzyme exclusively requires NADP+ or NADPH as the cofactor
Rauvolfia serpentina
NADPH
the enzyme exclusively requires NADP+ or NADPH as the cofactor
Rauvolfia serpentina
Ki Value [mM]
Ki Value [mM]
Ki Value maximum [mM]
Inhibitor
Commentary
Organism
Structure
0.53
-
menthol
pH 9.0, 25°C, versus 8-hydroxygeraniol
Rauvolfia serpentina
pI Value
Organism
Commentary
pI Value Maximum
pI Value
Rauvolfia serpentina
isoelectric focusing
-
5.4
Cofactor (protein specific)
Cofactor
Commentary
Organism
Structure
NADP+
the enzyme exclusively requires NADP+ or NADPH as the cofactor
Rauvolfia serpentina
NADPH
the enzyme exclusively requires NADP+ or NADPH as the cofactor
Rauvolfia serpentina
General Stability (protein specific)
General Stability
Organism
the enzyme rapidly and irreversibly loses its activity when 1 mM dithiothreitol and 20% glycerol v/v are omitted from the enzyme solution
Rauvolfia serpentina
Inhibitors (protein specific)
Inhibitors
Commentary
Organism
Structure
iridodial
-
Rauvolfia serpentina
isopulegol
-
Rauvolfia serpentina
menthol
competitive against 8-hydroxygeraniol
Rauvolfia serpentina
Ki Value [mM] (protein specific)
Ki Value [mM]
Ki Value maximum [mM]
Inhibitor
Commentary
Organism
Structure
0.53
-
menthol
pH 9.0, 25°C, versus 8-hydroxygeraniol
Rauvolfia serpentina
KM Value [mM] (protein specific)
KM Value [mM]
KM Value Maximum [mM]
Substrate
Commentary
Organism
Structure
additional information
-
additional information
steady-state kinetic studies show that the nerol dehydrogenation proceeds by an ordered Bi-Bi mechanism, NADP+ binds the enzyme first and then NADPH is the second product released from it, kinetic mechanism, overview
Rauvolfia serpentina
Metals/Ions (protein specific)
Metals/Ions
Commentary
Organism
Structure
additional information
the enzyme contains no Mo, Co, Cu, Fe, Mn, Mg, Ca, Se, Pt, and Au
Rauvolfia serpentina
Zn2+
the enzyme contains zinc ions
Rauvolfia serpentina
Molecular Weight [Da] (protein specific)
Molecular Weight [Da]
Molecular Weight Maximum [Da]
Commentary
Organism
44000
-
1 * 44000, SDS-PAGE
Rauvolfia serpentina
50000
-
native enzyme, gel filtration
Rauvolfia serpentina
Natural Substrates/ Products (Substrates) (protein specific)
Natural Substrates
Organism
Commentary (Nat. Sub.)
Natural Products
Commentary (Nat. Pro.)
Organism (Nat. Pro.)
Reversibility
(6E)-8-hydroxygeraniol + 2 NADP+
Rauvolfia serpentina
10-hydroxygeraniol undergoes a reversible dehydrogenation to produce 8-oxogeraniol or 8-hydroxygeranial, which are oxidized further to give 8-oxogeranial, the direct precursor of iridodial
(6E)-8-oxogeranial + 2 NADPH + 2 H+
-
-
r
additional information
Rauvolfia serpentina
various branched-chain allylic primary alcohols, such as nerol, geraniol, and 8-hydroxygeraniol, are substrates, but ethanol is inert. The enzyme is also active with farnesol, 3-methyl-2-buten1-ol, citronellol, 4-isopropylbenzyl alcohol, trans-2-heptenol, and trans-2-hexenol. The enzyme exclusively transfers the pro-R hydrogen of NADPH to neral. No activity with linalool, 2,6-dimethyl-octane, iridodial, 1-octanol, 1-heptanol, 1-pentanol, 3-methyl-3-buten-1-ol, trans-crotyl alcohol, isopulegol, and menthol
?
-
-
-
Purification (Commentary) (protein specific)
Commentary
Organism
native enzyme to homogeneity by ammonium sulfate fractionation, hydrophobic interaction, anion exchange, and AF-Red dye affinity chromatography followed by gel filtration
Rauvolfia serpentina
Specific Activity [micromol/min/mg] (protein specific)
Specific Activity Minimum [µmol/min/mg]
Specific Activity Maximum [µmol/min/mg]
Commentary
Organism
2.7
-
purified enzyme, pH 9.0, 25°C
Rauvolfia serpentina
Storage Stability (protein specific)
Storage Stability
Organism
-20°C, purified enzyme, 20 mM Tris HCl, pH 8.0, 20% glycerol, 1 mM DTT, 6 months without loss of activity
Rauvolfia serpentina
Substrates and Products (Substrate) (protein specific)
Substrates
Commentary Substrates
Literature (Substrates)
Organism
Products
Commentary (Products)
Literature (Products)
Organism (Products)
Reversibility
(6E)-8-hydroxygeraniol + 2 NADP+
-
717741
Rauvolfia serpentina
(6E)-8-oxogeranial + 2 NADPH + 2 H+
-
-
-
r
(6E)-8-hydroxygeraniol + 2 NADP+
10-hydroxygeraniol undergoes a reversible dehydrogenation to produce 8-oxogeraniol or 8-hydroxygeranial, which are oxidized further to give 8-oxogeranial, the direct precursor of iridodial
717741
Rauvolfia serpentina
(6E)-8-oxogeranial + 2 NADPH + 2 H+
-
-
-
r
(6E)-8-hydroxynerol + 2 NADP+
-
717741
Rauvolfia serpentina
? + 2 NADPH + 2 H+
-
-
-
r
geraniol + 2 NADP+
-
717741
Rauvolfia serpentina
? + 2 NADPH + 2 H+
-
-
-
r
additional information
various branched-chain allylic primary alcohols, such as nerol, geraniol, and 8-hydroxygeraniol, are substrates, but ethanol is inert. The enzyme is also active with farnesol, 3-methyl-2-buten1-ol, citronellol, 4-isopropylbenzyl alcohol, trans-2-heptenol, and trans-2-hexenol. The enzyme exclusively transfers the pro-R hydrogen of NADPH to neral. No activity with linalool, 2,6-dimethyl-octane, iridodial, 1-octanol, 1-heptanol, 1-pentanol, 3-methyl-3-buten-1-ol, trans-crotyl alcohol, isopulegol, and menthol
717741
Rauvolfia serpentina
?
-
-
-
-
nerol + 2 NADP+
-
717741
Rauvolfia serpentina
? + 2 NADPH + 2 H+
-
-
-
r
Subunits (protein specific)
Subunits
Commentary
Organism
monomer
1 * 44000, SDS-PAGE
Rauvolfia serpentina
Temperature Optimum [°C] (protein specific)
Temperature Optimum [°C]
Temperature Optimum Maximum [°C]
Commentary
Organism
25
-
assay at
Rauvolfia serpentina
pH Optimum (protein specific)
pH Optimum Minimum
pH Optimum Maximum
Commentary
Organism
7
-
reverse reaction assay at
Rauvolfia serpentina
9
-
forward reaction assay at
Rauvolfia serpentina
pI Value (protein specific)
Organism
Commentary
pI Value Maximum
pI Value
Rauvolfia serpentina
isoelectric focusing
-
5.4
General Information
General Information
Commentary
Organism
metabolism
the acyclic monoterpene primary alcohol:NADP+ oxidoreductase of Rauwolfia serpentina is a key enzyme in biosynthesis of monoterpene alcohols in the plant
Rauvolfia serpentina
General Information (protein specific)
General Information
Commentary
Organism
metabolism
the acyclic monoterpene primary alcohol:NADP+ oxidoreductase of Rauwolfia serpentina is a key enzyme in biosynthesis of monoterpene alcohols in the plant
Rauvolfia serpentina
Other publictions for EC 1.1.1.324
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)
717149
Hallahan
Purification and characterizat ...
Nepeta racemosa
Arch. Biochem. Biophys.
318
105-112
1995
-
1
-
-
-
-
6
1
1
1
2
2
-
3
-
-
1
-
-
1
1
-
4
1
1
-
-
-
1
-
-
2
-
-
-
-
1
-
2
-
-
-
-
6
-
1
1
1
2
2
-
-
-
1
-
1
1
-
4
1
1
-
-
-
1
-
-
-
-
1
1
-
-
-
717741
Ikeda
Acyclic monoterpene primary al ...
Rauvolfia serpentina
J. Biochem.
109
341-347
1991
-
-
-
-
-
1
3
1
-
2
2
2
-
2
-
-
1
-
-
-
1
1
6
1
1
-
-
-
2
-
-
2
1
1
-
-
-
-
2
-
-
1
-
3
1
1
-
2
2
2
-
-
-
1
-
-
1
1
6
1
1
-
-
-
2
-
-
1
-
1
1
-
-
-