1.14.11.11: hyoscyamine (6S)-dioxygenase
This is an abbreviated version!
For detailed information about hyoscyamine (6S)-dioxygenase, go to the full flat file.
Word Map on EC 1.14.11.11
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1.14.11.11
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scopolamine
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tropane
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hyoscyamus
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niger
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belladonna
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atropa
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anisodus
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anticholinergic
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hairy
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acutangulus
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anisodamine
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epoxidation
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2-oxoglutarate-dependent
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aerial
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6beta-hydroxylase
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solanaceous
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tanguticus
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agrobacterium-mediated
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metel
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putrescine
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datura
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n-methyltransferase
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tabacum
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chemotype
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high-value
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catharanthus
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pericycle
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roseus
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tropinone
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genetically-engineered
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biofunctional
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gst-tag
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vindoline
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underground
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bolt
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2.1.1.53
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drug development
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pharmacology
- 1.14.11.11
- scopolamine
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tropane
- hyoscyamus
- niger
- belladonna
-
atropa
-
anisodus
-
anticholinergic
-
hairy
- acutangulus
-
anisodamine
-
epoxidation
-
2-oxoglutarate-dependent
-
aerial
-
6beta-hydroxylase
-
solanaceous
- tanguticus
-
agrobacterium-mediated
- metel
- putrescine
- datura
- n-methyltransferase
- tabacum
-
chemotype
-
high-value
-
catharanthus
- pericycle
- roseus
- tropinone
-
genetically-engineered
-
biofunctional
-
gst-tag
- vindoline
-
underground
-
bolt
-
2.1.1.53
- drug development
- pharmacology
Reaction
Synonyms
6H6, AaH6H, AtH6H, Dih6h, H6H, HnH6H, hyoscyamine 6-hydroxylase, hyoscyamine 6beta-hydroxylase, hyoscyamine-6beta-hydroxylase, oxygenase, hyoscyamine 6beta-di-
ECTree
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Substrates Products
Substrates Products on EC 1.14.11.11 - hyoscyamine (6S)-dioxygenase
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REACTION DIAGRAM
(6S)-hydroxyhyoscyamine + succinate + CO2
L-hyoscyamine + 2-oxoglutarate + O2
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r
2-hydroxy-3-phenylpropionyltropine + 2-oxoglutarate + O2
2-hydroxy-3-phenylpropionyl-6-hydroxytropine + succinate + CO2
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15% of the activity with L-hyoscyamine
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?
2-oxoglutarate + p-hydroxyatropine + O2
?
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26% of the activity with L-hyoscyamine
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-
?
2-oxoglutarate + trans-cinnamoyltropine + O2
succinate + trans-cinnamoyl-6-hydroxytropine + CO2
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39% of the activity with L-hyoscyamine
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?
3-hydroxy-3-phenylpropionyltropine + 2-oxoglutarate + O2
3-hydroxy-3-phenylpropionyl-6-hydroxytropine + succinate + CO2
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56% of the activity with L-hyoscyamine
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?
6,7-dehydrohyoscyamine + 2-oxoglutarate + O2
scopolamine + succinate + CO2
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119% of the activity with L-hyoscyamine
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?
6beta-hydroxyhyoscyamine
scopolamine
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weak epoxidase activity, 2-5% of the hydroxylase activity
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-
?
8-methyl-8-azabicyclo[3.2.1]octan-3-yl 2-(4-(dimethylamino)phenyl)acetate + 2-oxoglutarate + O2
?
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-
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?
8-methyl-8-azabicyclo[3.2.1]octan-3-yl benzoate + 2-oxoglutarate + O2
?
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-
-
-
?
apoatropine + 2-oxoglutarate + O2
6-hydroxyapoatropine + succinate + CO2
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45% of the activity with L-hyoscyamine
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?
hyoscyamine + O2 + 2-oxoglutarate + O2
scopolamine + succinate + CO2
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-
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?
isobutyltropine + 2-oxoglutarate + O2
?
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15% of the activity with L-hyoscyamine
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?
L-homatropine + 2-oxoglutarate + O2
6-hydroxyhomatropine + succinate + CO2
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81% of the activity with L-hyoscyamine
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?
L-norhyoscyamine + 2-oxoglutarate + O2
6-hydroxynorhyoscyamine + succinate + CO2
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81% of the activity with L-hyoscyamine
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?
noratropine-N-acetic acid + 2-oxoglutarate + O2
?
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17% of the activity with L-hyoscyamine
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?
phenylacetyltropine + 2-oxoglutarate + O2
6-hydroxyphenylacetyltropine + succinate + CO2
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81% of the activity with L-hyoscyamine
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?
phenylalanyltropine + 2-oxoglutarate + O2
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8% of the activity with L-hyoscyamine
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-
?
scopolamine + succinate + CO2
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-
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?
(6S)-6-hydroxyhyoscyamine + 2-oxoglutarate + O2
scopolamine + succinate + CO2
key enzyme in the biosynthesis pathway of scopolamine
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?
(6S)-6-hydroxyhyoscyamine + 2-oxoglutarate + O2
scopolamine + succinate + CO2
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?
(6S)-6-hydroxyhyoscyamine + 2-oxoglutarate + O2
scopolamine + succinate + CO2
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-
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?
(6S)-6-hydroxyhyoscyamine + 2-oxoglutarate + O2
scopolamine + succinate + CO2
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ir
(6S)-hydroxyhyoscyamine + succinate + CO
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?
L-hyoscyamine + 2-oxoglutarate + O2
(6S)-hydroxyhyoscyamine + succinate + CO
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?
L-hyoscyamine + 2-oxoglutarate + O2
(6S)-hydroxyhyoscyamine + succinate + CO
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-
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?
L-hyoscyamine + 2-oxoglutarate + O2
(6S)-hydroxyhyoscyamine + succinate + CO
the bifunctional enzyme also catalyzes the conversion of (6S)-6beta-hydroxyhyoscyamine to scopolamine, cf. EC 1.14.20.13
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?
(6S)-hydroxyhyoscyamine + succinate + CO2
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?
L-hyoscyamine + 2-oxoglutarate + O2
(6S)-hydroxyhyoscyamine + succinate + CO2
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-
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?
L-hyoscyamine + 2-oxoglutarate + O2
(6S)-hydroxyhyoscyamine + succinate + CO2
the enzyme catalyzes the hydroxylation of (-)-hyoscyamine and the subsequent epoxidation of 6beta-hydroxyhyoscyamine to form scopolamine, a natural alkaloid
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?
L-hyoscyamine + 2-oxoglutarate + O2
(6S)-hydroxyhyoscyamine + succinate + CO2
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?
L-hyoscyamine + 2-oxoglutarate + O2
(6S)-hydroxyhyoscyamine + succinate + CO2
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?
L-hyoscyamine + 2-oxoglutarate + O2
(6S)-hydroxyhyoscyamine + succinate + CO2
MH392211
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?
L-hyoscyamine + 2-oxoglutarate + O2
(6S)-hydroxyhyoscyamine + succinate + CO2
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?
L-hyoscyamine + 2-oxoglutarate + O2
(6S)-hydroxyhyoscyamine + succinate + CO2
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H6H produces 6beta-hydroxyhyoscyamine and its derivative, scopolamine, the DmrH6H epoxidase activity is low compared to the hydroxylase activity
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?
L-hyoscyamine + 2-oxoglutarate + O2
(6S)-hydroxyhyoscyamine + succinate + CO2
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the binding of the substrates, hyoscyamine and 2-oxoglutarate, to the enzyme induces significant conformational changes
H6H produces 6beta-hydroxyhyoscyamine and its derivative, scopolamine, the DmrH6H epoxidase activity is low compared to the hydroxylase activity
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?
L-hyoscyamine + 2-oxoglutarate + O2
(6S)-hydroxyhyoscyamine + succinate + CO2
Glu116 interacts with the tertiary amine located on the hyoscyamine tropane moiety and Tyr326 forms CH-pi hydrogen bonds with the hyoscyamine phenyl ring
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?
L-hyoscyamine + 2-oxoglutarate + O2
(6S)-hydroxyhyoscyamine + succinate + CO2
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?
6beta-hydroxyhyoscyamine + succinate + CO2
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?
L-hyoscyamine + 2-oxoglutarate + O2
6beta-hydroxyhyoscyamine + succinate + CO2
key enzyme in the biosynthesis pathway of scopolamine
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?
L-hyoscyamine + 2-oxoglutarate + O2
6beta-hydroxyhyoscyamine + succinate + CO2
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?
L-hyoscyamine + 2-oxoglutarate + O2
6beta-hydroxyhyoscyamine + succinate + CO2
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?
L-hyoscyamine + 2-oxoglutarate + O2
6beta-hydroxyhyoscyamine + succinate + CO2
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?
L-hyoscyamine + 2-oxoglutarate + O2
6beta-hydroxyhyoscyamine + succinate + CO2
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?
L-hyoscyamine + 2-oxoglutarate + O2
6beta-hydroxyhyoscyamine + succinate + CO2
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?
L-hyoscyamine + 2-oxoglutarate + O2
6beta-hydroxyhyoscyamine + succinate + CO2
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?
L-hyoscyamine + 2-oxoglutarate + O2
6beta-hydroxyhyoscyamine + succinate + CO2
Hyoscyamus gyorffi
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?
L-hyoscyamine + 2-oxoglutarate + O2
6beta-hydroxyhyoscyamine + succinate + CO2
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?
L-hyoscyamine + 2-oxoglutarate + O2
6beta-hydroxyhyoscyamine + succinate + CO2
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?
L-hyoscyamine + 2-oxoglutarate + O2
6beta-hydroxyhyoscyamine + succinate + CO2
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?
L-hyoscyamine + 2-oxoglutarate + O2
6beta-hydroxyhyoscyamine + succinate + CO2
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?
L-hyoscyamine + 2-oxoglutarate + O2
6beta-hydroxyhyoscyamine + succinate + CO2
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?
L-hyoscyamine + 2-oxoglutarate + O2
6beta-hydroxyhyoscyamine + succinate + CO2
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?
L-hyoscyamine + 2-oxoglutarate + O2
6beta-hydroxyhyoscyamine + succinate + CO2
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?
L-hyoscyamine + 2-oxoglutarate + O2
6beta-hydroxyhyoscyamine + succinate + CO2
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ir
L-hyoscyamine + 2-oxoglutarate + O2
6beta-hydroxyhyoscyamine + succinate + CO2
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only the L-isomer of hyoscyamine serves as substrate, D-hyoscyamine is nearly inactive
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?
L-hyoscyamine + 2-oxoglutarate + O2
6beta-hydroxyhyoscyamine + succinate + CO2
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the enzyme catalyzes two consecutive oxidation reactions leading from hyoscyamine to scopolamine
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?
L-hyoscyamine + 2-oxoglutarate + O2
6beta-hydroxyhyoscyamine + succinate + CO2
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enzyme is involved in biosynthetic pathway leading to scopolamine
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L-hyoscyamine + 2-oxoglutarate + O2
6beta-hydroxyhyoscyamine + succinate + CO2
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?
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the enzyme also catalyzes the reaction of EC 1.14.11.14
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additional information
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the enzyme also catalyzes the reaction of EC 1.14.11.14
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additional information
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the enzyme also catalyzes the reaction of EC 1.14.11.14
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additional information
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hyoscyamine 6beta-hydroxylase, a 2-oxoglutarate-dependent dioxygenase, converts L-hyoscyamine to its 6,7-epoxy derivative, scopolamine, in two sequential steps. 6,7-Dehydrohyoscyamine, a potential precursor for the last step of epoxidation, is an obligatory intermediate in the biosynthesis of scopolamine
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additional information
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hyoscyamine 6beta-hydroxylase, a 2-oxoglutarate-dependent dioxygenase, converts L-hyoscyamine to its 6,7-epoxy derivative, scopolamine, in two sequential steps. The catalytic efficiency of AbH6H, especially for the second oxidation, which is the reaction of EC 1.14.11.14, is low. The epoxidation step is much slower than the hydroxylation step. Substrate analogues 1-methylpiperidin-4-yl 2-phenylacetate, 8-methyl-8-azabicyclo[3.2.1]octan-3-yl 3-phenylpropanoate, 8-oxabicyclo[3.2.1]octan-3-yl 2-phenylacetate, and 4 are no substrates for the enzyme
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additional information
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the enzyme also catalyzes the reaction of EC 1.14.11.14
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additional information
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high specificity for 2-oxoglutarate in hydroxylation
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additional information
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the enzyme also catalyzes the reaction of EC 1.14.11.14
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additional information
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the enzyme also catalyzes the reaction of EC 1.14.11.14
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?
additional information
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methyl jasmonate and salicylic acid increase the expression of the enzyme
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?