Information on EC 1.1.1.183 - geraniol dehydrogenase (NADP+)

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The enzyme appears in viruses and cellular organisms

EC NUMBER
COMMENTARY hide
1.1.1.183
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RECOMMENDED NAME
GeneOntology No.
geraniol dehydrogenase (NADP+)
REACTION
REACTION DIAGRAM
COMMENTARY hide
ORGANISM
UNIPROT
LITERATURE
geraniol + NADP+ = geranial + NADPH + H+
show the reaction diagram
REACTION TYPE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
oxidation
-
-
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redox reaction
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-
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reduction
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PATHWAY
BRENDA Link
KEGG Link
MetaCyc Link
Biosynthesis of antibiotics
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geraniol and geranial biosynthesis
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Geraniol degradation
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SYSTEMATIC NAME
IUBMB Comments
geraniol:NADP+ oxidoreductase
Also acts, more slowly on farnesol but not on nerol. The enzyme produces a mixture known as citral, which includes geranial and neral. It is still not known whether neral is produced directly by the enzyme, or by isomerization of geranial.
CAS REGISTRY NUMBER
COMMENTARY hide
56802-96-1
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ORGANISM
COMMENTARY hide
LITERATURE
UNIPROT
SEQUENCE DB
SOURCE
astigmatid mite
UniProt
Manually annotated by BRENDA team
Citrus sp.
orange
-
-
Manually annotated by BRENDA team
Stapf., lemongrass
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Manually annotated by BRENDA team
GEDH1; cv. Sweet Dani, gene GEDH1
SwissProt
Manually annotated by BRENDA team
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-
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Manually annotated by BRENDA team
cv. Scheurebe
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-
Manually annotated by BRENDA team
SUBSTRATE
PRODUCT                       
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate) hide
LITERATURE
(Substrate)
COMMENTARY
(Product) hide
LITERATURE
(Product)
Reversibility
r=reversible
ir=irreversible
?=not specified
2-heptanol + NADP+
2-heptanone + NADPH + H+
show the reaction diagram
-
-
-
-
r
2-heptonol + NADP+
2-heptanone + NADPH
show the reaction diagram
-
-
-
?
3-methyl-2-buten-1-ol + NADP+
3-methyl-2-butenal + NADPH
show the reaction diagram
22.7% of the activity with geraniol
-
-
?
3-methyl-3-buten-1-ol + NADP+
3-methyl-3-butenal + NADPH
show the reaction diagram
6.5% of the activity with geraniol
-
-
?
benzylalcohol + NADP+
benzaldehyde + NADPH
show the reaction diagram
5.5% of the activity with geraniol
-
-
?
beta-citronellol + NADP+
?
show the reaction diagram
-
compared to geraniol, isoform geraniol-DH I shows 72% activity and isoform geraniol-DH II shows 63% activity with this substrate
-
-
?
borneol + NADP+
?
show the reaction diagram
-
compared to geraniol, isoform geraniol-DH I shows 52% activity and isoform geraniol-DH II shows 29% activity with this substrate
-
-
?
carveol + NADP+
?
show the reaction diagram
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compared to geraniol, isoform geraniol-DH I shows 44% activity with this substrate
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-
?
cinnamyl alcohol + NADP+
?
show the reaction diagram
-
compared to geraniol, isoform geraniol-DH I shows 60% activity and isoform geraniol-DH II shows 50% activity with this substrate
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-
?
cinnamyl alcohol + NADP+
cinnamyl aldehyde + NADPH
show the reaction diagram
53.0% of the activity with geraniol
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-
?
cis-3-hexenol + NADP+
cis-3-hexenal + NADPH
show the reaction diagram
13.3% of the activity with geraniol
-
-
?
citronellol + NADP+
citronellal + NADPH
show the reaction diagram
citronellol + NADP+
citronellal + NADPH + H+
show the reaction diagram
-
-
-
-
r
E,E-farnesol + NAD+
?
show the reaction diagram
-
-
-
?
farnesol + NADP+
farnesal + NADPH
show the reaction diagram
Citrus sp.
-
-
-
?
geraniol + NAD+
geranial + NADH
show the reaction diagram
geraniol + NADP+
?
show the reaction diagram
geraniol + NADP+
geranial + NADPH
show the reaction diagram
geraniol + NADP+
geranial + NADPH + H+
show the reaction diagram
geraniol + NADP+
geranial NADPH
show the reaction diagram
heptanol + NADP+
heptanal + NADPH
show the reaction diagram
-
-
-
?
hexanol + NADP+
hexanal + NADPH
show the reaction diagram
31.6% of the activity with geraniol
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-
?
linalool + NADP+
?
show the reaction diagram
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compared to geraniol, isoform geraniol-DH I shows 42% activity and isoform geraniol-DH II shows 92% activity with this substrate
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-
?
nerol + NADP+
?
show the reaction diagram
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compared to geraniol, isoform geraniol-DH I shows 64% activity and isoform geraniol-DH II shows 50% activity with this substrate
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-
?
nerol + NADP+
neral + geranial + NADPH
show the reaction diagram
-
-
-
?
nerol + NADP+
neral + NADPH
show the reaction diagram
nerol + NADP+
neral + NADPH + H+
show the reaction diagram
-
-
-
-
r
p-cumic alcohol + NADP+
?
show the reaction diagram
-
compared to geraniol, isoform geraniol-DH I shows 56% activity and isoform geraniol-DH II shows 46% activity with this substrate
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-
?
phenylethanol + NADP+
phenylethanal + NADPH
show the reaction diagram
10.2% of the activity with geraniol
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?
phenylpropanol + NADP+
phenylpropanal + NADPH
show the reaction diagram
22.1% of the activity with geraniol
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?
additional information
?
-
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
citronellol + NADP+
citronellal + NADPH + H+
show the reaction diagram
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-
-
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r
geraniol + NAD+
geranial + NADH
show the reaction diagram
B2NI94
the enzyme plays an important role in the biosynthesis of neral, an alarm pheromone
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-
?
geraniol + NADP+
?
show the reaction diagram
geraniol + NADP+
geranial + NADPH
show the reaction diagram
geraniol + NADP+
geranial + NADPH + H+
show the reaction diagram
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-
-
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r
nerol + NADP+
neral + NADPH
show the reaction diagram
Q2KNL6
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-
-
r
nerol + NADP+
neral + NADPH + H+
show the reaction diagram
-
-
-
-
r
additional information
?
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determination and analysis, including isomerization steps, of the d6-geraniol metabolism in Vitis vinifera fruit mesocarp, overview
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COFACTOR
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
NAD+
specific for, no activity with NADP+
NADP+
NADPH
additional information
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METALS and IONS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
Zn2+
Citrus sp.
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suggested to be part of the enzyme
additional information
INHIBITORS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
(+)-limonene
Citrus sp.
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100% inhibition at 0.488 mM
2,2'-dipyridyl
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isoform geraniol-DH I shows 72% residual activity and geraniol-DH II shows 75% residual activity at 1 mM
8-hydroxyquinoline
Citrus sp.
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50% decrease at 0.67 mM
alpha,alpha'-dipyridyl
Citrus sp.
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50% inhibition at 25 mM
alpha-terpineol
Citrus sp.
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about 55% inhibition at 0.56 mM
cyanide
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isoforms geraniol-DH I and geraniol-DH II are completely inhibited at 1 mM
EDTA
Citrus sp.
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50% inhibition at 67.7 mM
iodoacetamide
linalool
Citrus sp.
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about 55% inhibition at 1.12 mM
MgCl2
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isoform geraniol-DH I shows 61% residual activity and geraniol-DH II shows 45% residual activity at 5 mM
N-bromosuccinimide
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o-phenanthroline
Citrus sp.
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50% inhibition at 16.7 mM
oxidized glutathione
Citrus sp.
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reaction completely stopped at 3.333 mM
SH-group-directed reagents
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Sodium azide
additional information
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imidazole and pyrazole, no effect
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ACTIVATING COMPOUND
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
2-mercaptoethanol
Citrus sp.
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protects enzyme from inhibition
additional information
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adding sodium metabisulfite, ascorbic acid, dithiothreitol, and EDTA to the extraction buffer and using Tris-HCl (pH 7.5) or potassium phosphate (pH 7.5) fails to enhance enzyme activity
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KM VALUE [mM]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
2.222 - 10
3,7-dimethyloct-6-en-1-ol
0.435 - 0.556
cinnamyl alcohol
0.1
geranial
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-
0.03 - 0.4
geraniol
0.741 - 1.333
linalool
0.0596
NAD+
pH 9.0, 25C
0.021 - 19.2
NADP+
0.037 - 1.212
nerol
SPECIFIC ACTIVITY [µmol/min/mg]
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
0.002
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cell free extract, in 100 mM glycine-NaOH, pH 9.5, at 37C
0.175
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isoform geraniol-DH I, after 116.7fold purification, in 100 mM glycine-NaOH, pH 9.5, at 37C
0.203
Citrus sp.
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-
0.261
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isoform geraniol-DH II, after 173.8fold purification, in 100 mM glycine-NaOH, pH 9.5, at 37C
31
purified enzyme
additional information
pH OPTIMUM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
6
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reduction reaction
6.5
Citrus sp.
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geranial reduction
pH RANGE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
5 - 10
Citrus sp.
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below 5 complete and irreversible inactivation after 5 min
6 - 10
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isoforms geraniol-DH I and geraniol-DH II show less than 40% activity below pH 6.5. Isoform geraniol-DH II shows no activity at pH 10.0, while isoform geraniol-DH I shows about 50% activity. Both isoforms are inactive at pH 6.0 and below
7 - 12
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below 7 loss of activity
8 - 12
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activity range, profile overview
8.5 - 10
over 72% of maximal activity at pH 8.5 and pH 10.0
TEMPERATURE OPTIMUM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
40
-
isoforms geraniol-DH I and geraniol-DH II
TEMPERATURE RANGE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
0 - 60
temprature profile, overview
pI VALUE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
3.5
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isoform geraniol-DH II, isoelectric focusing
8.8
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isoform geraniol-DH I, isoelectric focusing
SOURCE TISSUE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
SOURCE
additional information
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change in GeDH activity according to the degree of maturity and storage time of ginger of the two varieties, overview
Manually annotated by BRENDA team
MOLECULAR WEIGHT
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
40870
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x * 41000, SDS-PAGE, x * 40870, calculated
41000
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x * 41000, SDS-PAGE, x * 40870, calculated
42800
x * 42800, SDS-PAGE
56000
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1 * 56000 + 1 * 60000, isoform geraniol-DH II, SDS-PAGE
58000
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1 * 58000 + 1 * 62000, isoform geraniol-DH I, SDS-PAGE
60000
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1 * 56000 + 1 * 60000, isoform geraniol-DH II, SDS-PAGE
62000
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1 * 58000 + 1 * 62000, isoform geraniol-DH I, SDS-PAGE
92000
Citrus sp.
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estimation, gel filtration
100000
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isoform geraniol-DH I, gel filtration
120000
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isoform geraniol-DH II, gel filtration
SUBUNITS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
heterodimer
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1 * 56000 + 1 * 60000, isoform geraniol-DH II, SDS-PAGE; 1 * 58000 + 1 * 62000, isoform geraniol-DH I, SDS-PAGE
Crystallization/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
to 2.3 A resolution, space group P21212
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pH STABILITY
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
5 - 10
Citrus sp.
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below pH 5 complete and irreversible inactivation after 5 min
286130
7 - 12
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below pH 7 loss of activity
286132
8 - 9
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the enzyme activity in acetone extract is very stable at more than pH 8.0 and maximally at pH 9.0
286132
TEMPERATURE STABILITY
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
30 - 70
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rapid inactiviation of isoform geraniol-DH I occurs from 30-60C with 60% activity at 40C and 40% residual activity at 60C. At 70C the isoform shows less than 20% residual activity. Isoform geraniol-DH II retains over 80% activity after 10 min at 40C, while from 30-50C the activity decreases slightly and is lost at temperatures above 50C
STORAGE STABILITY
ORGANISM
UNIPROT
LITERATURE
-19C, dialyzed, rapid loss of activity
Citrus sp.
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-96C, undialyzed ammonium sulfate fraction, 6 months, quite active
Citrus sp.
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Purification/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
ammonium sulfate and 2-propanol fractionation
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DEAE Toyopearl 650M column chromatography, phenyl Toyopearl 650 M column chromatography, and AF-Red Toyopearl 650ML column chromatography
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native enzyme 1879fold to homogeneity by ammonium sulfate fractionation, followed by hydrophobic interactin and adsorption chromatography, anion exchange chromatography, and gel filtration in seven purification steps, overview
partially, ammonium sulfate fractionation, gel filtration, anion exchange chromatography
Citrus sp.
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recombinant GEDH1 from Escherichia coli by anion exchange chromatography
Cloned/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
DNA and amino acid sequence determination and analysis, phylogenetic analysis
expression in Escherichia coli
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GEDH1, phylogenetic tree and analysis, sequence comparison, expression in Escherichia coli
APPLICATION
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
nutrition
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high hydrostatic pressure treatment of grated ginger results in more than 95% inactivation of geraniol dehydrogenase. Heat treatment of 10 min at 100C inactivates geraniol dehydrogenase to 43% residual activity. In storage, untreated and heat-treated ginger shows reduction of geranial, neral, and citronellal while pressure-treated ginger does not. In the pressure-treated sample, terpene aldehydes almost disappear without the formation of the corresponding alcohols