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Information on EC 1.14.20.13 - 6beta-hydroxyhyoscyamine epoxidase and Organism(s) Hyoscyamus niger and UniProt Accession P24397
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1.14.20.13 6beta-hydroxyhyoscyamine epoxidaseIUBMB Comments
Requires Fe2+ and ascorbate.
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Word Map
- 1.14.20.13
- scopolamine
- hyoscyamus
-
tropane
- atropa
- niger
-
hairy
- belladonna
- shoot
-
1.14.11.11
- baetica
- tanguticus
-
agrobacterium
- rhizogenes
- nicotiana
-
2-oxoglutarate-dependent
-
anisodus
- datura
- muticus
- pharmacology
- putrescine
-
2.1.1.53
-
anisodamine
- tabacum
-
bioconversion
-
solanaceous
- synthesis
- n-methyltransferase
-
anticholinergic
The taxonomic range for the selected organisms is: Hyoscyamus niger
The enzyme appears in selected viruses and cellular organisms
The enzyme appears in selected viruses and cellular organisms
Reaction Schemes
Synonyms
hyoscyamine 6beta-hydroxylase, hyoscyamine-6beta-hydroxylase, 
more
topSYNONYM 
ORGANISM
UNIPROT
COMMENTARY 
LITERATURE
hydroxyhyoscyamine dioxygenase
-
-
-
-
REACTION TYPE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
redox reaction
-
-
-
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oxidation
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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
(6S)-6beta-hydroxyhyoscyamine,2-oxoglutarate oxidoreductase (epoxide-forming)
Requires Fe2+ and ascorbate.
CAS REGISTRY NUMBER
COMMENTARY
121479-53-6
-
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
(6S)-6beta-hydroxyhyoscyamine + 2-oxoglutarate + O2
scopolamine + succinate + CO2 + H2O
-
-
-
?
3-hydroxy-3-phenylpropionyltropine + 2-oxoglutarate + O2
3-hydroxy-3-phenylpropionyl-6-hydroxytropine + succinate + CO2 + H2O
-
-
-
?
6,7-dehydrohyoscyamine + 2-oxoglutarate + O2
scopolamine + succinate + CO2
-
-
-
?
apoatropine + 2-oxoglutarate + O2
6-hydroxyapoatropine + succinate + CO2 + H2O
-
-
-
?
l-homatropine + 2-oxoglutarate + O2
6-hydroxyhomatropine + succinate + CO2 + H2O
-
-
-
?
norhyoscyamine + 2-oxoglutarate + O2
6-hydroxynorhyoscyamine + succinate + CO2 + H2O
-
-
-
?
phenylacetyltropine + 2-oxoglutarate + O2
6-hydroxyphenylacetyltropine + succinate + CO2 + H2O
-
-
-
?
t-cinnamoyltropine + 2-oxoglutarate + O2
t-cinnamoyl-6-hydroxytropine + succinate + CO2 + H2O
-
-
-
?
(6S)-6beta-hydroxyhyoscyamine + 2-oxoglutarate + O2
scopolamine + succinate + CO2 + H2O
-
-
-
-
?
(6S)-6-hydroxyhyoscyamine + 2-oxoglutarate + O2
scopolamine + succinate + CO2
-
-
-
?
(6S)-6-hydroxyhyoscyamine + 2-oxoglutarate + O2
scopolamine + succinate + CO2
-
alkaloid metabolism, scopolamine is formed by oxidative transformation of hyoscyamine in several solanaceous species
-
?
additional information
?
-
enzyme catalyzes both the hydroxylation of hyoscyamine, reaction of EC 1.14.11.11, and the epoxidation of 6beta-hydroxyhyoscyamine to generate scopolamine
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-
?
additional information
?
-
-
enzyme is able to catalyze hydroxylation, dehydrogenation and in vitro epoxidation reactions all giving scopolamine. Hydroxyl rebound is unlikely to take place during the cyclization reaction and the hydroxylase versus oxidative cyclase activity is correlated with the presence of an exo-hydroxy group having syn-periplanar geometry with respect to the adjacent H atom to be abstracted
-
-
?
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
6,7-dehydrohyoscyamine + 2-oxoglutarate + O2
scopolamine + succinate + CO2
-
-
-
?
(6S)-6-hydroxyhyoscyamine + 2-oxoglutarate + O2
scopolamine + succinate + CO2
-
alkaloid metabolism, scopolamine is formed by oxidative transformation of hyoscyamine in several solanaceous species
-
?
COFACTOR
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
METALS and IONS
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
INHIBITOR
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
3,4-dihydroxybenzoate
competitive inhibitor with respect to 2-oxoglutarate
Pyridine 2,4-dicarboxylate
competitive inhibitor with respect to 2-oxoglutarate
additional information
-
no marked effect on enzyme activity by addition of NAD+, NADH, NADP+, NADPH, ATP + MgSO4, FAD, FMN, pyrroloquinoline quinone, acetyl-CoA, 6,7-dimethyl-5,6,7,8-tetrahydrofolate, phenazine methosulfate, 2,6-dichlorophenolindophenol, cytochrome c and H2O2
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ACTIVATING COMPOUND
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
KM VALUE [mM]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
Ki VALUE [mM]
INHIBITOR
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
SPECIFIC ACTIVITY [µmol/min/mg]
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
pH OPTIMUM
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
ORGANISM
COMMENTARY
LITERATURE
UNIPROT
SEQUENCE DB
SOURCE
SOURCE TISSUE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
SOURCE
LOCALIZATION
ORGANISM
UNIPROT
COMMENTARY
GeneOntology No.
LITERATURE
SOURCE
GENERAL INFORMATION
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
physiological function
physiological function
-
overexpression in hairy roots of Atropa baetica leeds to an altered alkaloid profile in which hyoscyamine is entirely converted into scopolamine. Scopolamine accumulation increases up to 9fold amounting to 5.6 mg per g dry weight
physiological function
Agrobacterium-mediated expression in non-hyoscyamine-producing Nicotiana tabacum and hyoscyamine-producing Hyoscyamus muticus. Transgenic Nicotiana tabacum hairy roots show a more efficient uptake of hyoscyamine from the culture medium and a higher rate of bioconversion of hyoscyamine to scopolamine than those of Hyoscamus muticus. The secretion of scopolamine in Nicotiana tabacum hairy roots is up to 85% of the total scopolamine being released to the culture medium. Exogenous hyoscyamine also causes changes in nicotine alkaloid accumulation in Nicotiana tabacum hairy roots
physiological function
root cultures overexpressing the enzyme show remarkably elevated levels of scopolamine and anisodamine. Hyoscyamine 6beta-hydroxylases from both Scopolia lurida and Hyoscyamus niger promote anisodamine production at similar levels in Scopolia lurida root cultures. Hyoscyamus niger hyoscyamine 6beta-hydroxylase overexpressing root cultures have more scopolamine in them than Scopolia lurida hyoscyamine 6beta-hydroxylase-overexpressing root cultures
UNIPROT
ENTRY NAME
ORGANISM
NO. OF AA
NO. OF TRANSM. HELICES
MOLECULAR WEIGHT[Da]
SOURCE
SEQUENCE
LOCALIZATION PREDICTION
The reliability class of the localization prediction ranges from 1 (very reliable) to 5 (not reliable).
The reliability class of the localization prediction ranges from 1 (very reliable) to 5 (not reliable). MOLECULAR WEIGHT
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
GENERAL STABILITY
ORGANISM
UNIPROT
LITERATURE
OXIDATION STABILITY
ORGANISM
UNIPROT
LITERATURE
STORAGE STABILITY
ORGANISM
UNIPROT
LITERATURE
PURIFICATION (Commentary)
ORGANISM
UNIPROT
LITERATURE
CLONED (Commentary)
ORGANISM
UNIPROT
LITERATURE
APPLICATION
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
synthesis
-
overexpression in hairy roots of Atropa baetica leeds to an altered alkaloid profile in which hyoscyamine is entirely converted into scopolamine. Scopolamine accumulation increases up to 9fold amounting to 5.6 mg per g dry weight
REF.
AUTHORS
TITLE
JOURNAL
VOL.
PAGES
YEAR
ORGANISM (UNIPROT)
PUBMED ID
SOURCE
Hashimoto, T.; Kohno, J.; Yamada, Y.
6beta-hydroxyhyoscyamine epoxidase from cultured roots of Hyoscyamus niger
Phytochemistry
28
1077-1082
1989
Hyoscyamus niger
-
Lan, X.; Zeng, J.; Liu, K.; Zhang, F.; Bai, G.; Chen, M.; Liao, Z.; Huang, L.
Comparison of two hyoscyamine 6beta-hydroxylases in engineering scopolamine biosynthesis in root cultures of Scopolia lurida
Biochem. Biophys. Res. Commun.
497
25-31
2018
Anisodus luridus, Hyoscyamus niger (P24397)
Zarate, R.; el Jaber-Vazdekis, N.; Medina, B.; Ravelo, A.G.
Tailoring tropane alkaloid accumulation in transgenic hairy roots of Atropa baetica by over-expressing the gene encoding hyoscyamine 6beta-hydroxylase
Biotechnol. Lett.
28
1271-1277
2006
Hyoscyamus niger
Hashimoto, T.; Yamada, Y.
Purification and characterization of hyoscyamine 6 beta-hydroxylase from root cultures of Hyoscyamus niger L. hydroxylase and epoxidase activities in the enzyme preparation
Eur. J. Biochem.
164
277-285
1987
Hyoscyamus niger (P24397)
Ushimaru, R.; Ruszczycky, M.W.; Chang, W.C.; Yan, F.; Liu, Y.N.; Liu, H.W.
Substrate conformation correlates with the outcome of hyoscyamine 6beta-hydroxylase catalyzed oxidation reactions
J. Am. Chem. Soc.
140
7433-7436
2018
Hyoscyamus niger
Haekkinen, S.T.; Moyano, E.; Cusido, R.M.; Palazon, J.; Pinol, M.T.; Oksman-Caldentey, K.M.
Enhanced secretion of tropane alkaloids in Nicotiana tabacum hairy roots expressing heterologous hyoscyamine-6beta-hydroxylase
J. Exp. Bot.
56
2611-2618
2005
Hyoscyamus niger (P24397), Hyoscyamus niger
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