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Information on EC 1.14.11.11 - hyoscyamine (6S)-dioxygenase and Organism(s) Hyoscyamus niger and UniProt Accession P24397

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IUBMB Comments
Requires Fe2+ and ascorbate.
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This record set is specific for:
Hyoscyamus niger
UNIPROT: P24397
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The taxonomic range for the selected organisms is: Hyoscyamus niger
The enzyme appears in selected viruses and cellular organisms
Synonyms
aah6h, hnh6h, dih6h, ath6h, more
SYNONYM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
hyoscyamine 6beta-hydroxylase
-
hyoscyamine 6-hydroxylase
-
-
-
-
hyoscyamine 6beta-hydroxylase
oxygenase, hyoscyamine 6beta-di-
-
-
-
-
REACTION TYPE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
decarboxylation
-
-
-
-
redox reaction
-
-
-
-
oxidation
-
-
-
-
reduction
-
-
-
-
hydroxylation
epoxidation
-
-
-
-
SYSTEMATIC NAME
IUBMB Comments
L-hyoscyamine,2-oxoglutarate:oxygen oxidoreductase ((6S)-hydroxylating)
Requires Fe2+ and ascorbate.
CAS REGISTRY NUMBER
COMMENTARY hide
103865-33-4
-
SUBSTRATE
PRODUCT                       
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate) hide
LITERATURE
(Substrate)
COMMENTARY
(Product) hide
LITERATURE
(Product)
Reversibility
r=reversible
ir=irreversible
?=not specified
(6S)-6-hydroxyhyoscyamine + 2-oxoglutarate + O2
scopolamine + succinate + CO2
show the reaction diagram
2-hydroxy-3-phenylpropionyltropine + 2-oxoglutarate + O2
2-hydroxy-3-phenylpropionyl-6-hydroxytropine + succinate + CO2
show the reaction diagram
-
15% of the activity with L-hyoscyamine
-
?
2-oxoglutarate + p-hydroxyatropine + O2
?
show the reaction diagram
-
26% of the activity with L-hyoscyamine
-
-
?
2-oxoglutarate + trans-cinnamoyltropine + O2
succinate + trans-cinnamoyl-6-hydroxytropine + CO2
show the reaction diagram
-
39% of the activity with L-hyoscyamine
-
?
3-hydroxy-3-phenylpropionyltropine + 2-oxoglutarate + O2
3-hydroxy-3-phenylpropionyl-6-hydroxytropine + succinate + CO2
show the reaction diagram
-
56% of the activity with L-hyoscyamine
-
?
6,7-dehydrohyoscyamine + 2-oxoglutarate + O2
scopolamine + succinate + CO2
show the reaction diagram
-
119% of the activity with L-hyoscyamine
-
?
6beta-hydroxyhyoscyamine
scopolamine
show the reaction diagram
-
weak epoxidase activity, 2-5% of the hydroxylase activity
-
-
?
apoatropine + 2-oxoglutarate + O2
6-hydroxyapoatropine + succinate + CO2
show the reaction diagram
-
45% of the activity with L-hyoscyamine
-
?
isobutyltropine + 2-oxoglutarate + O2
?
show the reaction diagram
-
15% of the activity with L-hyoscyamine
-
-
?
L-homatropine + 2-oxoglutarate + O2
6-hydroxyhomatropine + succinate + CO2
show the reaction diagram
-
81% of the activity with L-hyoscyamine
-
?
L-hyoscyamine + 2-oxoglutarate + O2
6beta-hydroxyhyoscyamine + succinate + CO2
show the reaction diagram
L-norhyoscyamine + 2-oxoglutarate + O2
6-hydroxynorhyoscyamine + succinate + CO2
show the reaction diagram
-
81% of the activity with L-hyoscyamine
-
?
noratropine-N-acetic acid + 2-oxoglutarate + O2
?
show the reaction diagram
-
17% of the activity with L-hyoscyamine
-
-
?
phenylacetyltropine + 2-oxoglutarate + O2
6-hydroxyphenylacetyltropine + succinate + CO2
show the reaction diagram
-
81% of the activity with L-hyoscyamine
-
?
phenylalanyltropine + 2-oxoglutarate + O2
?
show the reaction diagram
-
8% of the activity with L-hyoscyamine
-
-
?
additional information
?
-
-
high specificity for 2-oxoglutarate in hydroxylation
-
-
?
NATURAL SUBSTRATE
NATURAL PRODUCT
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate) hide
LITERATURE
(Substrate)
COMMENTARY
(Product) hide
LITERATURE
(Product)
REVERSIBILITY
r=reversible
ir=irreversible
?=not specified
(6S)-6-hydroxyhyoscyamine + 2-oxoglutarate + O2
scopolamine + succinate + CO2
show the reaction diagram
-
-
-
-
?
L-hyoscyamine + 2-oxoglutarate + O2
6beta-hydroxyhyoscyamine + succinate + CO2
show the reaction diagram
METALS and IONS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
INHIBITOR
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
1,10-phenanthroline
-
0.1 mM, 35% inhibition
2,2'-dipyridyl
-
0.1 mM, 15% inhibition
3,4-dihydroxybenzoate
-
-
3,4-dihydroxycinnamate
-
-
3,4-dihydroxymandelate
-
-
3,4-Dihydroxyphenylacetate
-
-
3,4-Dihydroxyphenylpropionate
-
-
3-oxoglutaric acid
-
-
5,7-dehydrohyoscyamine
-
-
Apoatropine
-
-
Bathocuproine
-
0.1 mM, 27% inhibition
Ca2+
-
0.4 mM, 11% inhibition
Cd2+
-
0.4 mM, complete inhibition
Co2+
-
0.4 mM, complete inhibition
Cu2+
-
0.4 mM, complete inhibition
diethyldithiocarbamate
-
0.1 mM, 37% inhibition
EDTA
-
0.1 mM, 67% inhibition
Fe3+
-
0.4 mM, 28% inhibition
fumarate
-
-
Hg2+
-
0.4 mM, 96% inhibition
L-Homatropine
-
-
Mn2+
-
0.4 mM, 95% inhibition
Ni2+
-
0.4 mM, 96% inhibition
nitroblue tetrazolium
-
-
Noratropine-N-acetic acid
-
-
Phenylacetyltropine
-
-
pyridine 2,3-dicarboxylate
-
competitive with respect to 2-oxoglutarate
Pyridine 2,4-dicarboxylate
-
competitive with respect to 2-oxoglutarate
Pyridine 3,4-dicarboxylate
-
-
Tiron
-
0.1 mM, 44% inhibition
Zn2+
-
0.4 mM, complete inhibition
ACTIVATING COMPOUND
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
5,7-dimethyl-5,6,7,8-tetrahydropterin
-
partial activation
acetone
-
10% v/v, activation
ascorbate
catalase
-
activation
-
dehydroascorbate
-
partial activation
dithiothreitol
isoascorbate
-
partial activation
KM VALUE [mM]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.043 - 0.057
2-oxoglutarate
0.01
6,7-Dehydrohyoscyamine
-
-
0.017 - 0.035
L-hyoscyamine
Ki VALUE [mM]
INHIBITOR
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.009
Pyridine 2,4-dicarboxylate
-
-
0.09
Pyridine 3,4-dicarboxylate
-
-
SPECIFIC ACTIVITY [µmol/min/mg]
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
additional information
-
-
pH OPTIMUM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
pH RANGE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
6 - 9
-
about 50% of maximal activity at pH 6.0 and pH 9.0
ORGANISM
COMMENTARY hide
LITERATURE
UNIPROT
SEQUENCE DB
SOURCE
-
SwissProt
Manually annotated by BRENDA team
SOURCE TISSUE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
SOURCE
additional information
-
mRNA of the hydroxylase is absent in leaves, stems and cultured cells
Manually annotated by BRENDA team
UNIPROT
ENTRY NAME
ORGANISM
NO. OF AA
NO. OF TRANSM. HELICES
MOLECULAR WEIGHT[Da]
SOURCE
SEQUENCE
LOCALIZATION PREDICTION?
HY6H_HYONI
344
0
39001
Swiss-Prot
other Location (Reliability: 3)
MOLECULAR WEIGHT
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
19000
-
x * 39000 + x * 19000, SDS-PAGE
38999
-
x * 38999, calculation from nucleotide sequence
39000
-
x * 39000 + x * 19000, SDS-PAGE
41000
-
gel filtration
SUBUNIT
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
PROTEIN VARIANTS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
D219H
-
inactive mutant enzyme
D219N
-
inactive mutant enzyme
H217Q
-
inactive mutant enzyme
H66Q
-
mutant enzyme has 97% of the activity of the wild-type enzyme
S274Q
-
inactive mutant enzyme
ORGANIC SOLVENT
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
Acetone
-
10% v/v, activation
STORAGE STABILITY
ORGANISM
UNIPROT
LITERATURE
-20°C, stable for more than 3 months
-
PURIFICATION (Commentary)
ORGANISM
UNIPROT
LITERATURE
CLONED (Commentary)
ORGANISM
UNIPROT
LITERATURE
overexpression in hairy root cultures of Scopolia lurida
T1 progeny of transgenic Atropa belladonna, in which putrescine N-methyltransferase (EC 2.1.1.53) from Nicotiana tabacum (NtPMT) and hyoscyamine 6beta-hydroxylase (EC 1.14.11.14) from Hyoscyamus niger (HnH6H) are overexpressed, are established to investigate tropane alkaloids biosynthesis and distribution in ripe fruits, leaves, stems, primary roots and secondary roots under field conditions. Both NtPMT and HnH6H are detected at the transcriptional level in transgenic plants, whereas they are not detected in wild-type plants. Metabolically engineered Atropa belladonna based on overexpressing NtPMT and HnH6H shows a chemotype of rich scopolamine that greatly improves the commercial and pharmaceutical properties of Atropa belladonna
cDNA from Hyoscyamus niger is simultaneously introduced into Nicotiana tabacum using particle bombardment and expressed under the control of the CaMV 35S promoter
-
expressed in Atropa baetica
-
expressed in Duboisia leichhardtii
-
expressed in Nicotiana tabacum and Hyoscyamus muticus
-
expression in Escherichia coli as a fusion protein to maltose-binding protein
-
the gene encoding hyosyamine 6-hydroxylase is placed under the regulation of the CaMV 35S promoter and introduced into the genome of a scopolamine-rich Duboisia hybrid by a binary vector system using Agrobacterium rhizogenes strain LBA9402. The scopolamine levels in the resulting engineered hairy root lines increases up to three times compared to wild-type hairy roots, but there is no clear increase in the engineered regenerated plants
-
APPLICATION
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
synthesis
overexpression of the enzyme (H6H) enhances the biosynthesis of anisodamine and scopolamine in hairy root cultures of Scopolia lurida, which should improve its commercial value. The tropane alkaloids anisodamine and and scopolamine are clinically used as anticholinergic agents
REF.
AUTHORS
TITLE
JOURNAL
VOL.
PAGES
YEAR
ORGANISM (UNIPROT)
PUBMED ID
SOURCE
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
Manually annotated by BRENDA team
Matsuda, J.; Okabe, S.; Hashimoto, T.; Yamada, Y.
Molecular cloning of hyoscyamine 6 beta-hydroxylase, a 2-oxoglutarate-dependent dioxygenase, from cultured roots of Hyoscyamus niger
J. Biol. Chem.
266
9460-9464
1991
Hyoscyamus niger
Manually annotated by BRENDA team
Hashimoto, T.; Yamada, Y.
Hyoscyamine 6beta-hydroxylase, a 2-oxoglutarate-dependent dioxygenase, an alkaloid-producing root cultures
Plant Physiol.
81
619-625
1986
Atropa belladonna, Datura metel, Duboisia leichhardtii, Hyoscyamus albus, Hyoscyamus gyorffi, Hyoscyamus muticus, Hyoscyamus niger, Hyoscyamus pusillus
Manually annotated by BRENDA team
Rocha, P.; Stenzel, O.; Parr, A.; Walton, N.; Christou, P.; Drager, B.; Leech, M.J.
Functional expression of tropinone reductase I (trI) and hyoscyamine-6beta-hydroxylase (h6h) from Hyoscyamus niger in Nicotiana tabacum
Plant Sci.
162
905-913
2002
Hyoscyamus niger
-
Manually annotated by BRENDA team
Yun, D.J.; Hashimoto, T.; Yamada, Y.
Transgenic tobacco plants with two consecutive oxidation reactions catalyzed by hyoscyamine 6b-hydroxylase
Biosci. Biotechnol. Biochem.
57
502-503
1993
Hyoscyamus niger
-
Manually annotated by BRENDA team
Matsuda, J.; Hashimoto, T.; Yamada, Y.
Analysis of active-site residues in hyoscyamine 6beta-hydroxylase
Plant Biotechnol.
14
51-57
1997
Hyoscyamus niger
-
Manually annotated by BRENDA team
Palazon, J.; Moyano, E.; Cusido, R.M.; Bonfill, M.; Oksman-Caldentey, K.M.; Pinol, M.T.
Alkaloid production in Duboisia hybrid hairy roots and plants overexpressing the h6h gene
Plant Sci.
165
1289-1295
2003
Hyoscyamus niger
-
Manually annotated by BRENDA team
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
Manually annotated by BRENDA team
Rahman, L.u.; Kitamura, Y.; Yamaguchi, J.; Mukai, M.; Akiyama, K.; Yamamoto, H.; Muranaka, T.; Ikenaga, T.
Exogenous plant H6H but not bacterial HCHL gene is expressed in Duboisia leichhardtii hairy roots and affects tropane alkaloid production
Enzyme Microb. Technol.
39
1183-1189
2006
Hyoscyamus niger
-
Manually annotated by BRENDA team
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
Manually annotated by BRENDA team
Xia, K.; Liu, X.; Zhang, Q.; Qiang, W.; Guo, J.; Lan, X.; Chen, M.; Liao, Z.
Promoting scopolamine biosynthesis in transgenic Atropa belladonna plants with pmt and h6h overexpression under field conditions
Plant Physiol. Biochem.
106
46-53
2016
Hyoscyamus niger (P24397), Hyoscyamus niger
Manually annotated by BRENDA team
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
Hyoscyamus niger (P24397), Hyoscyamus niger
Manually annotated by BRENDA team