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Enzyme Nomenclature
Information on EC 1.14.13.152 - geraniol 8-hydroxylase
Word Map on EC 1.14.13.152
- 1.14.13.152
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catharanthus
- roseus
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alkaloid
- indole
-
monooxygenase
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monoterpenoids
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iridoid
- strictosidine
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nadph-cytochrome
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ajmalicine
- vinblastine
- periwinkle
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co-overexpression
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methyljasmonate
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anti-cancer
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hairy
- anthranilate
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terpenoid
- vincristine
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The enzyme appears in viruses and cellular organisms
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EC NUMBER 
COMMENTARY 
1.14.13.152
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RECOMMENDED NAME
GeneOntology No.
geraniol 8-hydroxylase
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REACTION
REACTION DIAGRAM
COMMENTARY
ORGANISM
UNIPROT
LITERATURE
geraniol + NADPH + H+ + O2 = (6E)-8-hydroxygeraniol + NADP+ + H2O
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PATHWAY
BRENDA Link
KEGG Link
MetaCyc Link
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SYSTEMATIC NAME
IUBMB Comments
geraniol,NADPH:oxygen oxidoreductase (8-hydroxylating)
Requires cytochrome P-450. Also hydroxylates nerol and citronellol, cf. EC 1.14.13.151 linalool 8-monooxygenase. The recommended numbering of geraniol gives 8-hydroxygeraniol as the product rather than 10-hydroxygeraniol as used by references 1-3. See prenol nomenclature {iupac/misc/prenol#p1::Pr-1}. The cloned enzyme also catalysed, but less efficiently, the 3'-hydroxylation of naringenin (cf. EC 1.14.13.21, flavonoid 3'-monooxygenase) [3].
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CAS REGISTRY NUMBER
COMMENTARY
112198-82-0
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ORGANISM
COMMENTARY
LITERATURE
UNIPROT
SEQUENCE DB
SOURCE
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GENERAL INFORMATION
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
evolution
metabolism
physiological function
additional information
evolution
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the enzyme is a cyt P450 monoterpene hydroxylase and belongs to the cytochrome-P450 monooxygenase family
evolution
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the enzyme is a cyt P450 monoterpene hydroxylase and belongs to the cytochrome-P450 monooxygenase family
evolution
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the enzyme belongs to the cytochrome-P450 monooxygenase family
metabolism
G10H plays a role in the iridoid monoterpene and indole alkaloid biosynthesis; the enzyme plays an important role in the iridoid monoterpenoid and the indole alkaloid biosynthesis, overview
metabolism
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G10H catalyzes the first committed step of the biosynthetic pathway of strictosidine and other terpenoid indole alkaloids, overview
metabolism
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the enzyme is one of the key enzymes of the biosynthesis of monoterpene indole alkaloids that originate from the coupling of the indole and the iridoid pathways. Overview of metabolic pathways leading to the biosynthesis of monoterpene indole alkaloids and their metabolic regulation
metabolism
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G10H catalyses an early step of the biosynthesis of the monoterpene precursor of monoterpene indole alkaloids; the enzyme is involved in the monoterpene indole alkaloids, regulation of the enzyme activity involves two distinct calmodulin isoforms, CAM1 and CAM2, overview
metabolism
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the enzyme is involved in the biosynthesis of iridiod monoterpenoids
metabolism
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the enzyme is involved in the biosynthesis of iridiod monoterpenoids
metabolism
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the enzyme is catalyzing the first commited step to iridoid monoterpene biosynthesis and is involved in monoterpene indole alkaloid biosynthesis in specialized cells of the laticifer-idioblast system, overview
metabolism
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the enzyme is involved in the 2-C-methyl-D-erythritol-4-phosphate/terpenoid metabolic pathway part of the iridoid pathway, overview. Induction of G10H is a requirement, but not the only, necessary to produce other terpenoid indole alkaloids than strictosidine
metabolism
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the enzyme is involved in the biosynthesis of secologanin from geraniol, overview
physiological function
G10H hydroxylates geraniol and is involved in biosynthesis of swertiamarin via the iridoid pathway and of strictosidine via the indole pathway, overview, induced by methyljasmonate
physiological function
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geraniol 10-hydroxylase is a cytochrome P450 monooxygenase involved in the biosynthesis of iridoid monoterpenoids and several classes of monoterpenoid alkaloids found in a diverse range of plant species. G10H plays a key regulatory role in terpenoid indole alkaloid biosynthesis
physiological function
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the cytochrome P450 enzyme geraniol 10-hydroxylase plays an important role in the biosynthesis of pharmaceutically important alkaloids in Catharanthus roseus
physiological function
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the enzyme is involved in the biosynthesis of iridiod monoterpenoids, which are important in plant defense systems against herbivores
physiological function
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the enzyme is involved in the biosynthesis of iridiod monoterpenoids, which are important in plant defense systems against herbivores
physiological function
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the enzyme is catalyzing the first commited step to iridoid monoterpene biosynthesis and is involved in monoterpene indole alkaloid biosynthesis in specialized cells of the laticifer-idioblast system, overview
additional information
geraniol 10-hydroxylase is a cytochrome P450 monooxygenase
additional information
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geraniol 10-hydroxylase is a cytochrome P450 monooxygenase
additional information
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geraniol 10-hydroxylase is a cytochrome P450 monooxygenase
additional information
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geraniol 10-hydroxylase is a cytochrome P450 monooxygenase
additional information
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the individual overexpression of the terpenoid genes 1-deoxy-D-xylulose synthase, DXS, and G10H resulted in mixed results in regards to the accumulation of terpenoid indole alkaloid metabolite pools
additional information
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geraniol 10-hydroxylase is a cytochrome P450 monooxygenase. It consists of a reductase and a monooxygenase. The cytochrome P450 reductase, EC 1.6.2.4, is a membrane-bound flavoprotein, which transfers electrons from NADPH to the cytochrome P450 monooxygenase, CPR requires the cofactors FMN, FAD and NADPH
additional information
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the calmodulins CAM1 and CAM2 are required for monoterpene indole alkaloid biosynthesis in Catharanthus roseus cells by acting on regulation of expression of genes encoding enzymes that catalyse early steps of monoterpene indole alkaloid biosynthesis, such as 1-deoxy-D-xylulose 5-phosphate reductoisomerase and geraniol 10-hydroxylase, overview. CAM regulation by Ca2+, overview
additional information
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the transcription level of gene g10h is altered by treatment with Agrobacterium tumefaciens for induction of hariry root growth in second metabolite production, expression analysis, overview
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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
(R,S)-citronellol + NADPH + H+ + O2
(6E)-8-hydroxycitronellol + NADP+ + H2O
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GC-MS product analysis
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?
(R,S)-citronellol + NADPH + H+ + O2
(6E)-8-hydroxycitronellol + NADP+ + H2O
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GC-MS product analysis
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?
cis-nerol + NADPH + H+ + O2
(6E)-8-hydroxynerol + NADP+ + H2O
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GC-MS product analysis
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?
cis-nerol + NADPH + H+ + O2
(6E)-8-hydroxynerol + NADP+ + H2O
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GC-MS product analysis
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?
geraniol + NADPH + H+ + O2
(6E)-8-hydroxygeraniol + NADP+ + H2O
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-
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?
geraniol + NADPH + H+ + O2
(6E)-8-hydroxygeraniol + NADP+ + H2O
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GC-MS product analysis
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?
geraniol + NADPH + H+ + O2
(6E)-8-hydroxygeraniol + NADP+ + H2O
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GC-MS product analysis
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?
geraniol + NADPH + H+ + O2
10-hydroxygeraniol + NADP+ + H2O
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-
-
-
?
geraniol + NADPH + H+ + O2
10-hydroxygeraniol + NADP+ + H2O
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-
-
?
geraniol + NADPH + H+ + O2
10-hydroxygeraniol + NADP+ + H2O
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development and validation of an HPLC detection method for quantification of geraniol and 10-hydroxygeraniol, with separation of geraniol and nerol, overview
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-
?
geraniol + NADPH + H+ + O2
10-hydroxygeraniol + NADP+ + H2O
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mass spectrometrical product analysis
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?
geraniol + NADPH + H+ + O2
10-hydroxygeraniol + NADP+ + H2O
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?
nerol + NADPH + H+ + O2
10-hydroxynerol + NADP+ + H2O
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cis-isomer of geraniol
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?
nerol + NADPH + H+ + O2
10-hydroxynerol + NADP+ + H2O
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cis-isomer of geraniol
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?
additional information
?
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CrG10H also catalyzed 3'-hydroxylation of the flavanone naringenin to form eriodictyol, a reaction of the flavonoid 3'-hydroxylase. Analysis of the enzyme reactions of the recombinant enzyme with naringenin, apigenin, kaempferol, pcoumaric acid, and ferulic acid, mass spectrometric product analysis, overview
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additional information
?
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CYP76B10 is involved in production of swertiamarin
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additional information
?
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CYP76B10 is involved in production of swertiamarin
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NATURAL SUBSTRATES
NATURAL PRODUCTS
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
(R,S)-citronellol + NADPH + H+ + O2
(6E)-8-hydroxycitronellol + NADP+ + H2O
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-
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-
?
(R,S)-citronellol + NADPH + H+ + O2
(6E)-8-hydroxycitronellol + NADP+ + H2O
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-
-
-
?
geraniol + NADPH + H+ + O2
(6E)-8-hydroxygeraniol + NADP+ + H2O
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-
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?
geraniol + NADPH + H+ + O2
10-hydroxygeraniol + NADP+ + H2O
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?
geraniol + NADPH + H+ + O2
10-hydroxygeraniol + NADP+ + H2O
Q8VWZ7
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-
?
geraniol + NADPH + H+ + O2
10-hydroxygeraniol + NADP+ + H2O
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-
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-
?
nerol + NADPH + H+ + O2
10-hydroxynerol + NADP+ + H2O
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cis-isomer of geraniol
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-
?
nerol + NADPH + H+ + O2
10-hydroxynerol + NADP+ + H2O
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cis-isomer of geraniol
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?
additional information
?
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D1MI46
CYP76B10 is involved in production of swertiamarin
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additional information
?
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CYP76B10 is involved in production of swertiamarin
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COFACTOR
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
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INHIBITORS
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
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KM VALUE [mM]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
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TURNOVER NUMBER [1/s]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
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kcat/KM VALUE [1/mMs-1]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
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SPECIFIC ACTIVITY [µmol/min/mg]
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
8.66
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purified enzyme, pH 7.6, temperature not specified in the publication
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pH OPTIMUM
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
7.6
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TEMPERATURE OPTIMUM
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
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pI VALUE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
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SOURCE TISSUE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
SOURCE
additional information
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the enzyme is expressed in almost all tissues, except for flower and fruit, in situ RNA tissue hybridization, overview. Tissue localization of the enzyme and related primary metabolic pathways, overview
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G10H activity is correlated to the ability of the cells to accumulate terpenoid indole alkaloids. Alkaloid induction medium induces the enzyme, overview
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during the first week of growth, no activity in the stationary growth phase
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; expression analysis of G10H and other enzyme of the monoterpene indole alkaloid biosynthesis pathway, overview
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LOCALIZATION
ORGANISM
UNIPROT
COMMENTARY
GeneOntology No.
LITERATURE
SOURCE
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MOLECULAR WEIGHT
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
55500
x * 55500, about, sequence calculation; x * 55500, recombinant G10H, SDS-PAGE
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SUBUNITS
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
?
x * 55500, about, sequence calculation; x * 55500, recombinant G10H, SDS-PAGE
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Purification/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
native cholate-solubilized G10H about 8.3fold from suspension cell membranes by anion exchange and hydroxyapatite chromatography, and 2-aminooctyl agarose and a second step of hydrophobic interaction chromatography to homogeneity. Separation from the NADPH-cytochrome P-450 reductase, EC 1.6.2.4
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native enzyme about 12fold from membranes by anion exchange and omega-amino octyl agarose chromatography, followed by hydophobic interaction chromatography to homogeneity
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Cloned/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
cloning from a lambda-ZAPII library, recombinant expression in Saccharomyces cerevisiae strain YPH500 or in enzyme-deficient Catharathus roseus cell line MP183L, complementation
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co-expression of G10H with the NADPH-cytochrome P450 reductase from Arabidopsis thaliana in Spodoptera frugiperda Sf9 cell microsomes using the baculovirus transfection method, quantitative expression analysis
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expression in Spodoptera frugiperda SF9 cells, co-expression with NADPH:cytochrome P450 reductase NfCPR2 from Nothapodytes foetida and CPR2 from Arabidopsis thaliana
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gene CYP76B10, DNA and amino acid sequence determination and analysis, semi-quantitative RT-PCR expression analysis, sequence comparison and phylogenetic tree, expression in Pichia pastoris and in Escherichia coli; SmG10H, DNA and amno acid sequence determination and analysis, sequence comparisons and phylogenetic tree, semiquantitative RT-PCR expression analysis, recombinant expression in Escherichia coli strain BL21 and in Pichia pastoris
overexpression in Catharanthus roseus hairy roots via Agrobacterium rhizogenes 15834 transfection system, co-expression with the 1-deoxy-D-xylulose synthase, DXS, from Arabidopsis thaliana
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EXPRESSION
ORGANISM
UNIPROT
LITERATURE
effect of differential T-DNA transfer on transcript accumulation of MIA biosynthetic pathway genes, expression of gene g10h is 15 to 130fold increased, overview
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G10H expression, recombinant in Escherichia coli, is upregulated by methyljasmonate 6-36 h after treatment; methyljasmonate induces CYP76B10 expression
negative transcriptional regulation of geraniol 10-hydroxylase by calmodulin isozymes CAM1 and CAM2, overview
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the calmodulins CAM1 and CAM2 are required for monoterpene indole alkaloid biosynthesis in Catharanthus roseus cells by acting on regulation of expression of genes encoding enzymes that catalyse early steps of MIA biosynthesis, such as 1-deoxy-D-xylulose 5-phosphate reductoisomerase and geraniol 10-hydroxylase
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the stress hormone methyljasmonate strongly induces G10h gene expression coordinately with other terpenoid indole alkaloid biosynthesis genes in Catharanthus roseus cell culture
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the transcription level of gene g10h is increased 15 to 130fold by integration of T-DNA in host plant genome from root inducing Ri plasmid of Agrobacterium rhizogenes for induction of hariry root growth in second metabolite production, expression analysis in root clone CP68. Also the transcription of other genes involved in the monoterpene indole alkaloid biosynthetic pathway is altered, overview
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various hormones and elicitors upregulate G10H and the monoterpene alkaloid biosynthesis pathways. G10H activity is induced by phenobarbital
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ENGINEERING
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
additional information
additional information
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construction of hairy root lines with inducible overexpression of 1-deoxy-D-xylulose synthase, DXS, or geraniol-10-hydroxylase, G10H; co-overexpression of G10H with the 1-deoxy-D-xylulose synthase, DXS, from Arabidopsis thaliana causes a significant increase in ajmalicine by 16%, lochnericine by 31% and tabersonine by 13%. To increase the flux toward vinblastine and vincristine, a multiple genes within the pathway need to be overexpressed, terpenoid indole alkaloid profile, overview
additional information
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effect of differential T-DNA transfer on transcript accumulation of MIA biosynthetic pathway genes, expression of gene g10h is 15 to 130fold increased, overview
additional information
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microsomes isolated from insect cells co-expressing Nothapodytes foetida NfCPR2 and Catharanthus roseus geraniol 10-hydroxylase show enhanced the production of eriodictyol from naringenin approximately 11fold relative to control G10H-only insect cells, indicating the supportive role of NfCPR2 for G10H activity in insect cells. Addition of FAD and FMN up to 0.01 mM does not increase the supportive function of the NfCPR2 for G10H activity
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Renatured/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
reconstitution of the purified enzyme by addition of NADPH-cytochrome P-450 reductase, EC 1.6.2.4, and lipid extract
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LINKS TO OTHER DATABASES (specific for EC-Number 1.14.13.152)
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