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Information on EC 1.1.1.183 - geraniol dehydrogenase (NADP+)
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1.1.1.183 geraniol dehydrogenase (NADP+)IUBMB Comments
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.
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Word Map
- 1.1.1.183
- geranial
- citral
- neral
- dehydrogenases
-
monoterpene
-
lemongrass
- linalool
- cymbopogon
-
cis-isomer
- ginger
-
betaproteobacterium
- defragrans
-
geometric
-
castellaniella
- nutrition
The expected taxonomic range for this enzyme is: Eukaryota, Bacteria
Synonyms
geraniol dehydrogenase, gedh1, geraniol-dh i, 
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SYNONYM 
ORGANISM
UNIPROT
COMMENTARY 
LITERATURE
GeDH
additional information
additional information
the enzyme is a member of the medium-chain dehydrogenase/reductase family
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REACTION
REACTION DIAGRAM
COMMENTARY
ORGANISM
UNIPROT
LITERATURE
geraniol + NADP+ = geranial + NADPH + H+
also acts, more slowly, on nerol, farnesol and citronellol
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REACTION TYPE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
oxidation
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-
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redox reaction
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-
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reduction
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-
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PATHWAY SOURCE
PATHWAYS
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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.
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CAS REGISTRY NUMBER
COMMENTARY
56802-96-1
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SUBSTRATE
PRODUCT
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate)
(Substrate)
LITERATURE
(Substrate)
(Substrate)
COMMENTARY
(Product)
(Product)
LITERATURE
(Product)
(Product)
Reversibility
r=reversible
ir=irreversible
?=not specified
r=reversible
ir=irreversible
?=not specified
1-butanol + NADP+
butanal + NADPH + H+
5.4% activity compared to geraniol
-
-
?
3,7-dimethyloctanol + NADP+
3,7-dimethyloctanal + NADPH + H+
11.5% activity compared to geraniol
-
-
?
3-methyl-2-buten-1-ol + NADP+
3-methyl-2-buten-1-al + NADPH + H+
22.9% activity compared to geraniol
-
-
?
3-methyl-2-buten-1-ol + NADP+
3-methyl-2-butenal + NADPH
22.7% of the activity with geraniol
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-
?
3-methyl-2-buten-1-ol + NADP+
3-methyl-2-butenal + NADPH + H+
22.9% activity compared to geraniol
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-
?
3-methyl-3-buten-1-ol + NADP+
3-methyl-3-buten-1-al + NADPH + H+
6.9% activity compared to geraniol
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-
?
3-methyl-3-buten-1-ol + NADP+
3-methyl-3-butenal + NADPH
6.5% of the activity with geraniol
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-
?
3-methyl-3-buten-1-ol + NADP+
3-methyl-3-butenal + NADPH + H+
6.9% activity compared to geraniol
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-
?
3-phenylpropanol + NADP+
3-phenylpropanal + NADPH + H+
16.2% activity compared to geraniol
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?
benzylalcohol + NADP+
benzaldehyde + NADPH
5.5% of the activity with geraniol
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?
beta-citronellol + NADP+
?
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compared to geraniol, isoform geraniol-DH I shows 72% activity and isoform geraniol-DH II shows 63% activity with this substrate
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?
borneol + NADP+
?
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compared to geraniol, isoform geraniol-DH I shows 52% activity and isoform geraniol-DH II shows 29% activity with this substrate
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-
?
carveol + NADP+
?
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compared to geraniol, isoform geraniol-DH I shows 44% activity with this substrate
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-
?
cinnamyl alcohol + NADP+
?
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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+
cinnamaldehyde + NADPH + H+
31.6% activity compared to geraniol
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-
?
cinnamyl alcohol + NADP+
cinnamyl aldehyde + NADPH
53.0% of the activity with geraniol
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-
?
cinnamyl alcohol + NADP+
cinnamyl aldehyde + NADPH + H+
31.6% activity compared to geraniol
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-
?
cis-3-hexenol + NADP+
cis-3-hexenal + NADPH
13.3% of the activity with geraniol
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?
cis-3-hexenol + NADP+
cis-3-hexenal + NADPH + H+
11.9% activity compared to geraniol
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-
?
hexanol + NADP+
hexanal + NADPH
31.6% of the activity with geraniol
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?
hexanol + NADP+
hexanal + NADPH + H+
24.1% activity compared to geraniol
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-
?
linalool + NADP+
?
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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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-
?
n-butanol + NADP+
butanal + NADPH + H+
5.4% activity compared to geraniol
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-
?
nerol + NADP+
?
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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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-
?
p-cumic alcohol + NADP+
?
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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
10.2% of the activity with geraniol
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-
?
phenylethylalcohol + NADP+
phenylethylaldehyde + NADPH + H+
9.9% activity compared to geraniol
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-
?
phenylpropanol + NADP+
phenylpropanal + NADPH
22.1% of the activity with geraniol
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?
trans-2-hexenol + NADP+
trans-2-hexenal + NADPH + H+
26.6% activity compared to geraniol
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?
citronellol + NADP+
citronellal + NADPH
16.6% of the activity with geraniol
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r
citronellol + NADP+
citronellal + NADPH + H+
16.4% activity compared to geraniol
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?
geranial + NADPH + H+
geraniol + NADP+
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r
geranial + NADPH + H+
nerol + NADP+
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PcGeDH can reduce citral to geraniol and nerol when NADPH is added as cofactor, but not when NADP+ is the cofactor. PcGeDH can catalyze either oxidation or reduction. Oil component identification by gas mass spectrometry
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r
geranial + NADPH + H+
nerol + NADP+
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PcGeDH can reduce citral to geraniol and nerol when NADPH is added as cofactor, but not when NADP+ is the cofactor. PcGeDH can catalyze either oxidation or reduction. Oil component identification by gas mass spectrometry
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r
geraniol + NAD+
geranial + NADH + H+
the enzyme plays an important role in the biosynthesis of neral, an alarm pheromone
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?
geraniol + NAD+
geranial + NADH + H+
stereospecific reaction, no activity with nerol
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?
geraniol + NADP+
?
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most fundamental alcohol in the biosynthesis of terpenoids
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?
geraniol + NADP+
geranial + NADPH
the back reaction is catalyzed by CAD1, the cinnamyl alcohol dehydrogenase in vivo, the geraniol,/nerol pathway involves sveral dehydrogenases, overview
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ir
geraniol + NADP+
geranial + NADPH
the back reaction is catalyzed by CAD1, the cinnamyl alcohol dehydrogenase in vivo
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?
geraniol + NADP+
geranial + NADPH + H+
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?
geraniol + NADP+
geranial + NADPH + H+
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r
geraniol + NADP+
geranial + NADPH + H+
enzyme GeDH shows equal preference for geraniol and nerol
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r
nerol + NADP+
neral + NADPH + H+
101% of the activity with geraniol
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r
nerol + NADP+
neral + NADPH + H+
98.3% activity compared to geraniol
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r
nerol + NADP+
neral + NADPH + H+
enzyme GeDH shows equal preference for geraniol and nerol
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r
additional information
?
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substrate specificity, poor activity with citronellol, 3-methyl-2-buten-1-ol, 1-octanol, 1-butanol, 2-buten-1-ol, and ethanol, overview
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?
additional information
?
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substrate specificity, poor activity with citronellol, 3-methyl-2-buten-1-ol, 1-octanol, 1-butanol, 2-buten-1-ol, and ethanol, overview
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?
additional information
?
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Citrus sp.
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nerol, farnesol and citronellol are oxidized at slower rates
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?
additional information
?
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geraniol, geranial, neral and nerol formations are sequentially observed during cell culture
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?
additional information
?
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no activity with coniferyl alcohol, menthol, carveol, dihydrocarveol, 3,7-dimethyl-octanol, ethanol, butanol, and isobutanol
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?
additional information
?
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no activity with coniferyl alcohol, menthol, carveol, dihydrocarveol, 3,7-dimethyl-octanol, ethanol, butanol, and isobutanol
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?
additional information
?
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the overall reaction from geranyl diphosphate to citral is performed in vitro using geraniol synthase and GeDH from Perilla to form a large proportion of citral and relatively little geraniol as reaction products. Oil component identification by gas mass spectrometry
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?
additional information
?
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the overall reaction from geranyl diphosphate to citral is performed in vitro using geraniol synthase and GeDH from Perilla to form a large proportion of citral and relatively little geraniol as reaction products. Oil component identification by gas mass spectrometry
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?
additional information
?
-
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the overall reaction from geranyl diphosphate to citral is performed in vitro using geraniol synthase and GeDH from Perilla to form a large proportion of citral and relatively little geraniol as reaction products
-
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?
additional information
?
-
the overall reaction from geranyl diphosphate to citral is performed in vitro using geraniol synthase and GeDH from Perilla to form a large proportion of citral and relatively little geraniol as reaction products
-
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?
additional information
?
-
the overall reaction from geranyl diphosphate to citral is performed in vitro using geraniol synthase and GeDH from Perilla to form a large proportion of citral and relatively little geraniol as reaction products
-
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?
additional information
?
-
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the overall reaction from geranyl diphosphate to citral is performed in vitro using geraniol synthase and GeDH from Perilla to form a large proportion of citral and relatively little geraniol as reaction products. Oil component identification by gas mass spectrometry
-
-
?
additional information
?
-
the overall reaction from geranyl diphosphate to citral is performed in vitro using geraniol synthase and GeDH from Perilla to form a large proportion of citral and relatively little geraniol as reaction products. Oil component identification by gas mass spectrometry
-
-
?
additional information
?
-
the overall reaction from geranyl diphosphate to citral is performed in vitro using geraniol synthase and GeDH from Perilla to form a large proportion of citral and relatively little geraniol as reaction products. Oil component identification by gas mass spectrometry
-
-
?
additional information
?
-
the overall reaction from geranyl diphosphate to citral is performed in vitro using geraniol synthase and GeDH from Perilla to form a large proportion of citral and relatively little geraniol as reaction products. Oil component identification by gas mass spectrometry
-
-
?
additional information
?
-
the overall reaction from geranyl diphosphate to citral is performed in vitro using geraniol synthase and GeDH from Perilla to form a large proportion of citral and relatively little geraniol as reaction products
-
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?
additional information
?
-
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tetrahydrogeraniol, tetrahydrolinalool, menthol, benzyl alcohol, and farnesol are no substrates for both isoforms. Isoform geraniol-DH II does not react with 3,7-dihydrolinalool, and isoform geraniol-DH I does not react with carveol
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?
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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?
additional information
?
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no activity with borneol, menthol, benzyl alcohol and ethanol. Geraniol, nerol and citronellol are structurally similar acyclic monoterpene alcohols
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?
additional information
?
-
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the enzyme shows no activity with borneol, menthol, benzyl alcohol, and ethanol
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?
additional information
?
-
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feeding exeriments with cell culture: the incorporated geraniol and geranyl acetate are transformed and detected (by GC-MS) as geranial, geraniol, geranyl acetate and citronellol, while nerol and neral are hardly detected
-
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?
additional information
?
-
feeding exeriments with cell culture: the incorporated geraniol and geranyl acetate are transformed and detected (by GC-MS) as geranial, geraniol, geranyl acetate and citronellol, while nerol and neral are hardly detected
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?
additional information
?
-
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the recombinant ZoGeDH catalyzes the NADP+-dependent oxidation from geraniol to citral, a mixture of geranial and neral, but the neral content in vivo is very low. Its substrate specificity is the highest for geraniol and nerol, while that for cinnamyl alcohol is 32% of the activity observed for geraniol
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?
additional information
?
-
the recombinant ZoGeDH catalyzes the NADP+-dependent oxidation from geraniol to citral, a mixture of geranial and neral, but the neral content in vivo is very low. Its substrate specificity is the highest for geraniol and nerol, while that for cinnamyl alcohol is 32% of the activity observed for geraniol
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?
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NATURAL SUBSTRATE
NATURAL PRODUCT
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate)
(Substrate)
LITERATURE
(Substrate)
(Substrate)
COMMENTARY
(Product)
(Product)
LITERATURE
(Product)
(Product)
REVERSIBILITY
r=reversible
ir=irreversible
?=not specified
r=reversible
ir=irreversible
?=not specified
geraniol + NAD+
geranial + NADH + H+
the enzyme plays an important role in the biosynthesis of neral, an alarm pheromone
-
-
?
geraniol + NADP+
?
-
most fundamental alcohol in the biosynthesis of terpenoids
-
-
?
geraniol + NADP+
geranial + NADPH
the back reaction is catalyzed by CAD1, the cinnamyl alcohol dehydrogenase in vivo, the geraniol,/nerol pathway involves sveral dehydrogenases, overview
-
-
ir
geraniol + NADP+
geranial + NADPH + H+
-
-
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?
geraniol + NADP+
geranial + NADPH + H+
-
-
-
r
nerol + NADP+
neral + NADPH + H+
enzyme GeDH shows equal preference for geraniol and nerol
-
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r
additional information
?
-
geraniol, geranial, neral and nerol formations are sequentially observed during cell culture
-
-
?
additional information
?
-
the overall reaction from geranyl diphosphate to citral is performed in vitro using geraniol synthase and GeDH from Perilla to form a large proportion of citral and relatively little geraniol as reaction products. Oil component identification by gas mass spectrometry
-
-
?
additional information
?
-
the overall reaction from geranyl diphosphate to citral is performed in vitro using geraniol synthase and GeDH from Perilla to form a large proportion of citral and relatively little geraniol as reaction products. Oil component identification by gas mass spectrometry
-
-
?
additional information
?
-
-
the overall reaction from geranyl diphosphate to citral is performed in vitro using geraniol synthase and GeDH from Perilla to form a large proportion of citral and relatively little geraniol as reaction products
-
-
?
additional information
?
-
the overall reaction from geranyl diphosphate to citral is performed in vitro using geraniol synthase and GeDH from Perilla to form a large proportion of citral and relatively little geraniol as reaction products
-
-
?
additional information
?
-
the overall reaction from geranyl diphosphate to citral is performed in vitro using geraniol synthase and GeDH from Perilla to form a large proportion of citral and relatively little geraniol as reaction products
-
-
?
additional information
?
-
the overall reaction from geranyl diphosphate to citral is performed in vitro using geraniol synthase and GeDH from Perilla to form a large proportion of citral and relatively little geraniol as reaction products
-
-
?
additional information
?
-
-
determination and analysis, including isomerization steps, of the d6-geraniol metabolism in Vitis vinifera fruit mesocarp, overview
-
-
?
additional information
?
-
-
feeding exeriments with cell culture: the incorporated geraniol and geranyl acetate are transformed and detected (by GC-MS) as geranial, geraniol, geranyl acetate and citronellol, while nerol and neral are hardly detected
-
-
?
additional information
?
-
feeding exeriments with cell culture: the incorporated geraniol and geranyl acetate are transformed and detected (by GC-MS) as geranial, geraniol, geranyl acetate and citronellol, while nerol and neral are hardly detected
-
-
?
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COFACTOR
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
additional information
-
no activity is observed when NAD+ is substituted for NADP+
-
additional information
no activity is observed when NAD+ is substituted for NADP+
-
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METALS and IONS
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
Zn2+
additional information
additional information
the enzyme is not affected by Na+, K+, NH4+, Ca2+, and Mg2+
additional information
-
the enzyme is not affected by Na+, K+, NH4+, Ca2+, and Mg2+
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INHIBITOR
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
2,2'-dipyridyl
-
isoform geraniol-DH I shows 72% residual activity and geraniol-DH II shows 75% residual activity at 1 mM
cyanide
-
isoforms geraniol-DH I and geraniol-DH II are completely inhibited at 1 mM
MgCl2
-
isoform geraniol-DH I shows 61% residual activity and geraniol-DH II shows 45% residual activity at 5 mM
iodoacetamide
-
isoforms geraniol-DH I and geraniol-DH II are completely inhibited at 1 mM
Sodium azide
-
isoform geraniol-DH I shows 61% residual activity and geraniol-DH II shows 90% residual activity at 1 mM
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ACTIVATING COMPOUND
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
additional information
-
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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