Information on EC 1.1.1.324 - 8-hydroxygeraniol dehydrogenase

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The enzyme appears in viruses and cellular organisms

EC NUMBER
COMMENTARY hide
1.1.1.324
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RECOMMENDED NAME
GeneOntology No.
8-hydroxygeraniol dehydrogenase
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REACTION
REACTION DIAGRAM
COMMENTARY hide
ORGANISM
UNIPROT
LITERATURE
(6E)-8-hydroxygeranial + NADP+ = (6E)-8-oxogeranial + NADPH + H+
show the reaction diagram
1c
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(6E)-8-hydroxygeraniol + 2 NADP+ = (6E)-8-oxogeranial + 2 NADPH + 2 H+
show the reaction diagram
overall reaction
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(6E)-8-hydroxygeraniol + NADP+ = (6E)-8-hydroxygeranial + NADPH + H+
show the reaction diagram
1a
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(6E)-8-hydroxygeraniol + NADP+ = (6E)-8-oxogeraniol + NADPH + H+
show the reaction diagram
1b
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(6E)-8-oxogeraniol + NADP+ = (6E)-8-oxogeranial + NADPH + H+
show the reaction diagram
1d
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PATHWAY
BRENDA Link
KEGG Link
MetaCyc Link
secologanin and strictosidine biosynthesis
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Monoterpenoid biosynthesis
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Metabolic pathways
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Biosynthesis of secondary metabolites
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SYSTEMATIC NAME
IUBMB Comments
(6E)-8-hydroxygeraniol:NADP+ oxidoreductase
Contains Zn2+. The enzyme catalyses the oxidation of (6E)-8-hydroxygeraniol to (6E)-8-oxogeranial via either (6E)-8-hydroxygeranial or (6E)-8-oxogeraniol. Also acts on geraniol, nerol and citronellol. May be identical to EC 1.1.1.183 geraniol dehydrogenase. The recommended numbering of geraniol gives 8-hydroxygeraniol as the substrate rather than 10-hydroxygeraniol as used by references 1 and 2. See prenol nomenclature {iupac/misc/prenol#p1::Pr-1}.
CAS REGISTRY NUMBER
COMMENTARY hide
133249-46-4
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ORGANISM
COMMENTARY hide
LITERATURE
UNIPROT
SEQUENCE DB
SOURCE
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Manually annotated by BRENDA team
GENERAL INFORMATION
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
metabolism
SUBSTRATE
PRODUCT                       
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate) hide
LITERATURE
(Substrate)
COMMENTARY
(Product) hide
LITERATURE
(Product)
Reversibility
r=reversible
ir=irreversible
?=not specified
(6E)-8-hydroxygeraniol + 2 NADP+
(6E)-8-oxogeranial + 2 NADPH + 2 H+
show the reaction diagram
(6E)-8-hydroxynerol + 2 NADP+
? + 2 NADPH + 2 H+
show the reaction diagram
geraniol + 2 NADP+
? + 2 NADPH + 2 H+
show the reaction diagram
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r
nerol + 2 NADP+
? + 2 NADPH + 2 H+
show the reaction diagram
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r
additional information
?
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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
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NATURAL SUBSTRATES
NATURAL PRODUCTS
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate) hide
LITERATURE
(Substrate)
COMMENTARY
(Product) hide
LITERATURE
(Product)
REVERSIBILITY
r=reversible
ir=irreversible
?=not specified
(6E)-8-hydroxygeraniol + 2 NADP+
(6E)-8-oxogeranial + 2 NADPH + 2 H+
show the reaction diagram
(6E)-8-hydroxynerol + 2 NADP+
? + 2 NADPH + 2 H+
show the reaction diagram
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?
additional information
?
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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
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COFACTOR
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
NADP+
NADPH
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the enzyme exclusively requires NADP+ or NADPH as the cofactor
additional information
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no activity with NAD+
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METALS and IONS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
additional information
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the enzyme contains no Mo, Co, Cu, Fe, Mn, Mg, Ca, Se, Pt, and Au
INHIBITORS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
1,10-phenanthroline
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79% inhibition at 1.0 mM, 87% at 10 mM
4-chloromercuribenzoate
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complete inhibition at 1 mM and above
EDTA
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44% inhibition at 100 mM
iodoacetamide
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5% inhibition at 1.0 mM, 22% at 10 mM
isopulegol
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menthol
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competitive against 8-hydroxygeraniol
NEM
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55% inhibition at 1.0 mM, complete inhibition at 10 mM
Triton X-100
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potent inhibition at 0.01-0.1%
KM VALUE [mM]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.018
NADP+
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with 8-hydroxynerol, pH 9.5, 25C
additional information
additional information
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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
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Ki VALUE [mM]
INHIBITOR
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.53
menthol
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pH 9.0, 25C, versus 8-hydroxygeraniol
SPECIFIC ACTIVITY [µmol/min/mg]
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
2.7
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purified enzyme, pH 9.0, 25C
1417
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purified enzyme, pH 9.5, 25C
pH OPTIMUM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
7
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reverse reaction assay at
9
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forward reaction assay at
TEMPERATURE OPTIMUM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
pI VALUE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
5.4
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isoelectric focusing
SOURCE TISSUE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
SOURCE
LOCALIZATION
ORGANISM
UNIPROT
COMMENTARY hide
GeneOntology No.
LITERATURE
SOURCE
MOLECULAR WEIGHT
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
50000
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native enzyme, gel filtration
63000
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gel filtration
SUBUNITS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
dimer
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1 * 40000 + 1 x 42000, SDS-PAGE
monomer
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1 * 44000, SDS-PAGE
GENERAL STABILITY
ORGANISM
UNIPROT
LITERATURE
the enzyme rapidly and irreversibly loses its activity when 1 mM dithiothreitol and 20% glycerol v/v are omitted from the enzyme solution
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STORAGE STABILITY
ORGANISM
UNIPROT
LITERATURE
-20C, purified enzyme, 20 mM Tris HCl, pH 8.0, 20% glycerol, 1 mM DTT, 6 months without loss of activity
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Purification/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
native enzyme 1149fold from leaves to homogeneity by ultracentrifugation, ammonium sulfate fractionation, hydrophobic inetraction and anion exchange chromatography, affinity chromatography, and gel filtration
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native enzyme to homogeneity by ammonium sulfate fractionation, hydrophobic interaction, anion exchange, and AF-Red dye affinity chromatography followed by gel filtration
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APPLICATION
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
additional information
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plant (4aR,7S,7aS)-nepetalactone can be used for synthesis of (4aR,7S,7aS)-nepetalactol, an aphid pheromone, useful in aphid control