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Information on EC 1.14.11.11 - hyoscyamine (6S)-dioxygenase
for references in articles please use BRENDA:EC1.14.11.11
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EC Tree 1 Oxidoreductases
1.14 Acting on paired donors, with incorporation or reduction of molecular oxygen
1.14.11 With 2-oxoglutarate as one donor, and incorporation of one atom of oxygen into each donor
1.14.11.11 hyoscyamine (6S)-dioxygenase
IUBMB Comments
Requires Fe2+ and ascorbate.
The enzyme appears in viruses and cellular organisms
- 1.14.11.11
- scopolamine
-
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 Schemes
showSynonyms
aah6h, hnh6h, dih6h, ath6h, more
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SYNONYM 
ORGANISM
UNIPROT
COMMENTARY 
LITERATURE
H6H
hyoscyamine 6-hydroxylase
-
-
-
-
hyoscyamine 6beta-hydroxylase
hyoscyamine-6beta-hydroxylase
oxygenase, hyoscyamine 6beta-di-
-
-
-
-
hyoscyamine 6beta-hydroxylase
-
-
-
-
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REACTION
REACTION DIAGRAM
COMMENTARY
ORGANISM
UNIPROT
LITERATURE
L-hyoscyamine + 2-oxoglutarate + O2 = (6S)-hydroxyhyoscyamine + succinate + CO2
-
-
-
-
L-hyoscyamine + 2-oxoglutarate + O2 = (6S)-hydroxyhyoscyamine + succinate + CO2
proposed mechanism of epoxidation catalyzed by the enzyme, overview
-
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REACTION TYPE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
decarboxylation
-
-
-
-
epoxidation
-
-
-
-
hydroxylation
oxidation
-
-
-
-
redox reaction
-
-
-
-
reduction
-
-
-
-
hydroxylation
-
-
-
-
hydroxylation
-
converts L-hyoscyamine to 6beta-hydroxyhyoscyamine and then to scopolamine
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PATHWAY SOURCE
PATHWAYS
MetaCyc
superpathway of hyoscyamine (atropine) and scopolamine biosynthesis, tropane alkaloids biosynthesis
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SYSTEMATIC NAME
IUBMB Comments
L-hyoscyamine,2-oxoglutarate:oxygen oxidoreductase ((6S)-hydroxylating)
Requires Fe2+ and ascorbate.
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CAS REGISTRY NUMBER
COMMENTARY
103865-33-4
-
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SUBSTRATE
PRODUCT
REACTION DIAGRAM
ORGANISM
UNIPROT
LITERATURE
COMMENTARY
Reversibility
r=reversible
ir=irreversible
?=not specified
r=reversible
ir=irreversible
?=not specified
(6S)-hydroxyhyoscyamine + succinate + CO2
L-hyoscyamine + 2-oxoglutarate + O2
Substrates: -
Products: -
Products: -
r
2-hydroxy-3-phenylpropionyltropine + 2-oxoglutarate + O2
2-hydroxy-3-phenylpropionyl-6-hydroxytropine + succinate + CO2
-
Substrates: 15% of the activity with L-hyoscyamine
Products: -
Products: -
?
2-oxoglutarate + p-hydroxyatropine + O2
?
-
Substrates: 26% of the activity with L-hyoscyamine
Products: -
Products: -
?
2-oxoglutarate + trans-cinnamoyltropine + O2
succinate + trans-cinnamoyl-6-hydroxytropine + CO2
-
Substrates: 39% of the activity with L-hyoscyamine
Products: -
Products: -
?
3-hydroxy-3-phenylpropionyltropine + 2-oxoglutarate + O2
3-hydroxy-3-phenylpropionyl-6-hydroxytropine + succinate + CO2
-
Substrates: 56% of the activity with L-hyoscyamine
Products: -
Products: -
?
6,7-dehydrohyoscyamine + 2-oxoglutarate + O2
scopolamine + succinate + CO2
-
Substrates: 119% of the activity with L-hyoscyamine
Products: -
Products: -
?
6beta-hydroxyhyoscyamine
scopolamine
-
Substrates: weak epoxidase activity, 2-5% of the hydroxylase activity
Products: -
Products: -
?
6beta-hydroxyhyoscyamine + ?
scopolamine + ?
Substrates: -
Products: -
Products: -
?
8-methyl-8-azabicyclo[3.2.1]octan-3-yl 2-(4-(dimethylamino)phenyl)acetate + 2-oxoglutarate + O2
?
-
Substrates: -
Products: -
Products: -
?
8-methyl-8-azabicyclo[3.2.1]octan-3-yl benzoate + 2-oxoglutarate + O2
?
-
Substrates: -
Products: -
Products: -
?
apoatropine + 2-oxoglutarate + O2
6-hydroxyapoatropine + succinate + CO2
-
Substrates: 45% of the activity with L-hyoscyamine
Products: -
Products: -
?
hyoscyamine + O2 + 2-oxoglutarate + O2
scopolamine + succinate + CO2
-
Substrates: -
Products: -
Products: -
?
isobutyltropine + 2-oxoglutarate + O2
?
-
Substrates: 15% of the activity with L-hyoscyamine
Products: -
Products: -
?
L-homatropine + 2-oxoglutarate + O2
6-hydroxyhomatropine + succinate + CO2
-
Substrates: 81% of the activity with L-hyoscyamine
Products: -
Products: -
?
L-norhyoscyamine + 2-oxoglutarate + O2
6-hydroxynorhyoscyamine + succinate + CO2
-
Substrates: 81% of the activity with L-hyoscyamine
Products: -
Products: -
?
noratropine-N-acetic acid + 2-oxoglutarate + O2
?
-
Substrates: 17% of the activity with L-hyoscyamine
Products: -
Products: -
?
phenylacetyltropine + 2-oxoglutarate + O2
6-hydroxyphenylacetyltropine + succinate + CO2
-
Substrates: 81% of the activity with L-hyoscyamine
Products: -
Products: -
?
phenylalanyltropine + 2-oxoglutarate + O2
?
-
Substrates: 8% of the activity with L-hyoscyamine
Products: -
Products: -
?
(6S)-6-hydroxyhyoscyamine + 2-oxoglutarate + O2
scopolamine + succinate + CO2
Substrates: -
Products: -
Products: -
?
(6S)-6-hydroxyhyoscyamine + 2-oxoglutarate + O2
scopolamine + succinate + CO2
Substrates: key enzyme in the biosynthesis pathway of scopolamine
Products: -
Products: -
?
(6S)-6-hydroxyhyoscyamine + 2-oxoglutarate + O2
scopolamine + succinate + CO2
Substrates: -
Products: -
Products: -
?
(6S)-6-hydroxyhyoscyamine + 2-oxoglutarate + O2
scopolamine + succinate + CO2
-
Substrates: -
Products: -
Products: -
?
(6S)-6-hydroxyhyoscyamine + 2-oxoglutarate + O2
scopolamine + succinate + CO2
-
Substrates: -
Products: -
Products: -
ir
L-hyoscyamine + 2-oxoglutarate + O2
(6S)-hydroxyhyoscyamine + succinate + CO
-
Substrates: -
Products: -
Products: -
?
L-hyoscyamine + 2-oxoglutarate + O2
(6S)-hydroxyhyoscyamine + succinate + CO
Substrates: -
Products: -
Products: -
?
L-hyoscyamine + 2-oxoglutarate + O2
(6S)-hydroxyhyoscyamine + succinate + CO
Substrates: -
Products: -
Products: -
?
L-hyoscyamine + 2-oxoglutarate + O2
(6S)-hydroxyhyoscyamine + succinate + CO
Substrates: the bifunctional enzyme also catalyzes the conversion of (6S)-6beta-hydroxyhyoscyamine to scopolamine, cf. EC 1.14.20.13
Products: -
Products: -
?
L-hyoscyamine + 2-oxoglutarate + O2
(6S)-hydroxyhyoscyamine + succinate + CO2
Substrates: -
Products: -
Products: -
?
L-hyoscyamine + 2-oxoglutarate + O2
(6S)-hydroxyhyoscyamine + succinate + CO2
-
Substrates: -
Products: -
Products: -
?
L-hyoscyamine + 2-oxoglutarate + O2
(6S)-hydroxyhyoscyamine + succinate + CO2
Substrates: the enzyme catalyzes the hydroxylation of (-)-hyoscyamine and the subsequent epoxidation of 6beta-hydroxyhyoscyamine to form scopolamine, a natural alkaloid
Products: -
Products: -
?
L-hyoscyamine + 2-oxoglutarate + O2
(6S)-hydroxyhyoscyamine + succinate + CO2
-
Substrates: -
Products: -
Products: -
?
L-hyoscyamine + 2-oxoglutarate + O2
(6S)-hydroxyhyoscyamine + succinate + CO2
Substrates: -
Products: -
Products: -
?
L-hyoscyamine + 2-oxoglutarate + O2
(6S)-hydroxyhyoscyamine + succinate + CO2
MH392211
Substrates: -
Products: -
Products: -
?
L-hyoscyamine + 2-oxoglutarate + O2
(6S)-hydroxyhyoscyamine + succinate + CO2
Substrates: -
Products: -
Products: -
?
L-hyoscyamine + 2-oxoglutarate + O2
(6S)-hydroxyhyoscyamine + succinate + CO2
-
Substrates: -
Products: H6H produces 6beta-hydroxyhyoscyamine and its derivative, scopolamine, the DmrH6H epoxidase activity is low compared to the hydroxylase activity
Products: H6H produces 6beta-hydroxyhyoscyamine and its derivative, scopolamine, the DmrH6H epoxidase activity is low compared to the hydroxylase activity
?
L-hyoscyamine + 2-oxoglutarate + O2
(6S)-hydroxyhyoscyamine + succinate + CO2
-
Substrates: the binding of the substrates, hyoscyamine and 2-oxoglutarate, to the enzyme induces significant conformational changes
Products: H6H produces 6beta-hydroxyhyoscyamine and its derivative, scopolamine, the DmrH6H epoxidase activity is low compared to the hydroxylase activity
Products: H6H produces 6beta-hydroxyhyoscyamine and its derivative, scopolamine, the DmrH6H epoxidase activity is low compared to the hydroxylase activity
?
L-hyoscyamine + 2-oxoglutarate + O2
(6S)-hydroxyhyoscyamine + succinate + CO2
Substrates: Glu116 interacts with the tertiary amine located on the hyoscyamine tropane moiety and Tyr326 forms CH-pi hydrogen bonds with the hyoscyamine phenyl ring
Products: -
Products: -
?
L-hyoscyamine + 2-oxoglutarate + O2
(6S)-hydroxyhyoscyamine + succinate + CO2
Substrates: -
Products: -
Products: -
?
L-hyoscyamine + 2-oxoglutarate + O2
6beta-hydroxyhyoscyamine + succinate + CO2
Substrates: -
Products: -
Products: -
?
L-hyoscyamine + 2-oxoglutarate + O2
6beta-hydroxyhyoscyamine + succinate + CO2
Substrates: key enzyme in the biosynthesis pathway of scopolamine
Products: -
Products: -
?
L-hyoscyamine + 2-oxoglutarate + O2
6beta-hydroxyhyoscyamine + succinate + CO2
Substrates: -
Products: -
Products: -
?
L-hyoscyamine + 2-oxoglutarate + O2
6beta-hydroxyhyoscyamine + succinate + CO2
-
Substrates: -
Products: -
Products: -
?
L-hyoscyamine + 2-oxoglutarate + O2
6beta-hydroxyhyoscyamine + succinate + CO2
-
Substrates: -
Products: -
Products: -
?
L-hyoscyamine + 2-oxoglutarate + O2
6beta-hydroxyhyoscyamine + succinate + CO2
-
Substrates: -
Products: -
Products: -
?
L-hyoscyamine + 2-oxoglutarate + O2
6beta-hydroxyhyoscyamine + succinate + CO2
-
Substrates: -
Products: -
Products: -
?
L-hyoscyamine + 2-oxoglutarate + O2
6beta-hydroxyhyoscyamine + succinate + CO2
Hyoscyamus gyorffi
-
Substrates: -
Products: -
Products: -
?
L-hyoscyamine + 2-oxoglutarate + O2
6beta-hydroxyhyoscyamine + succinate + CO2
-
Substrates: -
Products: -
Products: -
?
L-hyoscyamine + 2-oxoglutarate + O2
6beta-hydroxyhyoscyamine + succinate + CO2
-
Substrates: -
Products: -
Products: -
?
L-hyoscyamine + 2-oxoglutarate + O2
6beta-hydroxyhyoscyamine + succinate + CO2
-
Substrates: -
Products: -
Products: -
ir
L-hyoscyamine + 2-oxoglutarate + O2
6beta-hydroxyhyoscyamine + succinate + CO2
-
Substrates: only the L-isomer of hyoscyamine serves as substrate, D-hyoscyamine is nearly inactive
Products: -
Products: -
?
L-hyoscyamine + 2-oxoglutarate + O2
6beta-hydroxyhyoscyamine + succinate + CO2
-
Substrates: the enzyme catalyzes two consecutive oxidation reactions leading from hyoscyamine to scopolamine
Products: -
Products: -
?
L-hyoscyamine + 2-oxoglutarate + O2
6beta-hydroxyhyoscyamine + succinate + CO2
-
Substrates: enzyme is involved in biosynthetic pathway leading to scopolamine
Products: -
Products: -
?
L-hyoscyamine + 2-oxoglutarate + O2
6beta-hydroxyhyoscyamine + succinate + CO2
-
Substrates: -
Products: -
Products: -
?
additional information
?
-
Substrates: the enzyme also catalyzes the reaction of EC 1.14.11.14
Products: -
Products: -
?
additional information
?
-
-
Substrates: the enzyme also catalyzes the reaction of EC 1.14.11.14
Products: -
Products: -
?
additional information
?
-
-
Substrates: the enzyme also catalyzes the reaction of EC 1.14.11.14
Products: -
Products: -
?
additional information
?
-
-
Substrates: 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
Products: -
Products: -
?
additional information
?
-
-
Substrates: 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
Products: -
Products: -
?
additional information
?
-
Substrates: the enzyme also catalyzes the reaction of EC 1.14.11.14
Products: -
Products: -
?
additional information
?
-
-
Substrates: high specificity for 2-oxoglutarate in hydroxylation
Products: -
Products: -
?
additional information
?
-
Substrates: the enzyme also catalyzes the reaction of EC 1.14.11.14
Products: -
Products: -
?
additional information
?
-
-
Substrates: the enzyme also catalyzes the reaction of EC 1.14.11.14
Products: -
Products: -
?
additional information
?
-
-
Substrates: methyl jasmonate and salicylic acid increase the expression of the enzyme
Products: -
Products: -
?
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NATURAL SUBSTRATE
NATURAL PRODUCT
REACTION DIAGRAM
ORGANISM
UNIPROT
LITERATURE
COMMENTARY
REVERSIBILITY
r=reversible
ir=irreversible
?=not specified
r=reversible
ir=irreversible
?=not specified
(6S)-6-hydroxyhyoscyamine + 2-oxoglutarate + O2
scopolamine + succinate + CO2
Substrates: key enzyme in the biosynthesis pathway of scopolamine
Products: -
Products: -
?
(6S)-6-hydroxyhyoscyamine + 2-oxoglutarate + O2
scopolamine + succinate + CO2
-
Substrates: -
Products: -
Products: -
?
L-hyoscyamine + 2-oxoglutarate + O2
(6S)-hydroxyhyoscyamine + succinate + CO
-
Substrates: -
Products: -
Products: -
?
L-hyoscyamine + 2-oxoglutarate + O2
(6S)-hydroxyhyoscyamine + succinate + CO
Substrates: -
Products: -
Products: -
?
L-hyoscyamine + 2-oxoglutarate + O2
(6S)-hydroxyhyoscyamine + succinate + CO
Substrates: -
Products: -
Products: -
?
L-hyoscyamine + 2-oxoglutarate + O2
(6S)-hydroxyhyoscyamine + succinate + CO2
Substrates: -
Products: -
Products: -
?
L-hyoscyamine + 2-oxoglutarate + O2
(6S)-hydroxyhyoscyamine + succinate + CO2
-
Substrates: -
Products: -
Products: -
?
L-hyoscyamine + 2-oxoglutarate + O2
(6S)-hydroxyhyoscyamine + succinate + CO2
Substrates: the enzyme catalyzes the hydroxylation of (-)-hyoscyamine and the subsequent epoxidation of 6beta-hydroxyhyoscyamine to form scopolamine, a natural alkaloid
Products: -
Products: -
?
L-hyoscyamine + 2-oxoglutarate + O2
(6S)-hydroxyhyoscyamine + succinate + CO2
-
Substrates: -
Products: -
Products: -
?
L-hyoscyamine + 2-oxoglutarate + O2
(6S)-hydroxyhyoscyamine + succinate + CO2
Substrates: -
Products: -
Products: -
?
L-hyoscyamine + 2-oxoglutarate + O2
(6S)-hydroxyhyoscyamine + succinate + CO2
MH392211
Substrates: -
Products: -
Products: -
?
L-hyoscyamine + 2-oxoglutarate + O2
(6S)-hydroxyhyoscyamine + succinate + CO2
Substrates: -
Products: -
Products: -
?
L-hyoscyamine + 2-oxoglutarate + O2
(6S)-hydroxyhyoscyamine + succinate + CO2
-
Substrates: -
Products: H6H produces 6beta-hydroxyhyoscyamine and its derivative, scopolamine, the DmrH6H epoxidase activity is low compared to the hydroxylase activity
Products: H6H produces 6beta-hydroxyhyoscyamine and its derivative, scopolamine, the DmrH6H epoxidase activity is low compared to the hydroxylase activity
?
L-hyoscyamine + 2-oxoglutarate + O2
(6S)-hydroxyhyoscyamine + succinate + CO2
Substrates: -
Products: -
Products: -
?
L-hyoscyamine + 2-oxoglutarate + O2
6beta-hydroxyhyoscyamine + succinate + CO2
Substrates: key enzyme in the biosynthesis pathway of scopolamine
Products: -
Products: -
?
L-hyoscyamine + 2-oxoglutarate + O2
6beta-hydroxyhyoscyamine + succinate + CO2
-
Substrates: -
Products: -
Products: -
?
L-hyoscyamine + 2-oxoglutarate + O2
6beta-hydroxyhyoscyamine + succinate + CO2
-
Substrates: the enzyme catalyzes two consecutive oxidation reactions leading from hyoscyamine to scopolamine
Products: -
Products: -
?
L-hyoscyamine + 2-oxoglutarate + O2
6beta-hydroxyhyoscyamine + succinate + CO2
-
Substrates: enzyme is involved in biosynthetic pathway leading to scopolamine
Products: -
Products: -
?
additional information
?
-
-
Substrates: 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
Products: -
Products: -
?
additional information
?
-
-
Substrates: methyl jasmonate and salicylic acid increase the expression of the enzyme
Products: -
Products: -
?
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METALS and IONS
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
Fe2+
Fe2+
without addition of Fe2+, only 1.3% of the activity is detected
Fe2+
-
dependent, about 25-30% decreased production of scopolamine and hyoscyamine in absence of iron in medium
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INHIBITOR
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
(1R,2R,4S,5S,7s)-7-{[(2S)-3-hydroxy-2-phenylpropanoyl]oxy}-9,9-dimethyl-3-oxa-9-azoniatricyclo[3.3.1.02,4]nonane
-
slight inhibition by the substrate analogue
8-methyl-8-azabicyclo[3.2.1]octan-3-yl 2-(4-(dimethylamino)phenyl)acetate
-
-
additional information
-
synthesis and inhibitory potencies of substrate analogues, overview. No inhibition by substrate analogues 1-methylpiperidin-4-yl 2-phenylacetate, 8-methyl-8-azabicyclo[3.2.1]octan-3-yl 3-phenylpropanoate, and 8-oxabicyclo[3.2.1]octan-3-yl 2-phenylacetate
-
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ACTIVATING COMPOUND
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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Ki VALUE [mM]
INHIBITOR
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE