Information on EC 1.1.1.206 - tropinone reductase I

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The expected taxonomic range for this enzyme is: Eukaryota, Bacteria

EC NUMBER
COMMENTARY hide
1.1.1.206
-
RECOMMENDED NAME
GeneOntology No.
tropinone reductase I
REACTION
REACTION DIAGRAM
COMMENTARY hide
ORGANISM
UNIPROT
LITERATURE
tropine + NADP+ = tropinone + NADPH + H+
show the reaction diagram
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-
-
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REACTION TYPE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
oxidation
-
-
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redox reaction
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-
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reduction
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PATHWAY
BRENDA Link
KEGG Link
MetaCyc Link
hyoscyamine and scopolamine biosynthesis
-
-
superpathway of hyoscyamine and scopolamine biosynthesis
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Tropane, piperidine and pyridine alkaloid biosynthesis
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Metabolic pathways
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Biosynthesis of secondary metabolites
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SYSTEMATIC NAME
IUBMB Comments
tropine:NADP+ 3alpha-oxidoreductase
Also oxidizes other tropan-3alpha-ols, but not the corresponding beta-derivatives [1]. This enzyme along with EC 1.1.1.236, tropinone reductase II, represents a branch point in tropane alkaloid metabolism [4]. Tropine (the product of EC 1.1.1.206) is incorporated into hyoscyamine and scopolamine whereas pseudotropine (the product of EC 1.1.1.236) is the first specific metabolite on the pathway to the calystegines [4]. Both enzymes are always found together in any given tropane-alkaloid-producing species, have a common substrate, tropinone, and are strictly stereospecific [3].
CAS REGISTRY NUMBER
COMMENTARY hide
82532-89-6
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ORGANISM
COMMENTARY hide
LITERATURE
UNIPROT
SEQUENCE DB
SOURCE
Atropa acuminata
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-
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Manually annotated by BRENDA team
formerly Datura arborea
UniProt
Manually annotated by BRENDA team
Brugmansia sp.
candida x aurea hybrid
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-
Manually annotated by BRENDA team
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-
-
Manually annotated by BRENDA team
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-
-
Manually annotated by BRENDA team
Hyoscyamus bohemicus
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-
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Manually annotated by BRENDA team
Hyoscyamus canariensis
-
-
-
Manually annotated by BRENDA team
and strain Hn11
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-
Manually annotated by BRENDA team
no activity in Brassica campestris
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-
-
Manually annotated by BRENDA team
no activity in Browallia americana
-
-
-
Manually annotated by BRENDA team
no activity in Calystegia sepium
-
-
-
Manually annotated by BRENDA team
no activity in Nicotiana tabacum
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-
-
Manually annotated by BRENDA team
no activity in Physalis alkekengi
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-
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Manually annotated by BRENDA team
Physalis edulis
-
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Manually annotated by BRENDA team
AT3
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-
Manually annotated by BRENDA team
AT3
-
-
Manually annotated by BRENDA team
Scopolia atropoides
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-
-
Manually annotated by BRENDA team
gene trI
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Manually annotated by BRENDA team
cv. Desiree
UniProt
Manually annotated by BRENDA team
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UniProt
Manually annotated by BRENDA team
cv. NMITLI-118
UniProt
Manually annotated by BRENDA team
GENERAL INFORMATION
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
evolution
metabolism
physiological function
additional information
SUBSTRATE
PRODUCT                       
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate) hide
LITERATURE
(Substrate)
COMMENTARY
(Product) hide
LITERATURE
(Product)
Reversibility
r=reversible
ir=irreversible
?=not specified
1-methylpyrrolidine + NADPH + H+
? + NADP+
show the reaction diagram
-
-
-
?
1-propyl-4-piperidone + NADPH + H+
1-propylpiperidin-4-ol + NADP+
show the reaction diagram
low activity
-
-
?
1-propyl-4-piperidone + NADPH + H+
? + NADP+
show the reaction diagram
-
-
-
?
2-pyrrolidone + NADPH + H+
2-hydroxypyrrolidine + NADP+
show the reaction diagram
very low activity
-
-
?
2-pyrrolidone + NADPH + H+
? + NADP+
show the reaction diagram
-
-
-
?
3-methyl-cyclohexanone + NADPH
3-methylcyclohexanol + NADP+
show the reaction diagram
-
85% of the reaction velocity with tropinone
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-
?
3-methylcyclohexanone + NADP+
3-methylcyclohexanol + NADP+
show the reaction diagram
-
-
-
?
3-methylcyclohexanone + NADPH
3-methylcyclohexanol + NADP+
show the reaction diagram
3-methylcyclohexanone + NADPH + H+
3-methylcyclohexanol + NADP+
show the reaction diagram
-
-
-
?
3-methylcyclohexanone + NADPH + H+
? + NADP+
show the reaction diagram
-
-
-
?
3-quinuclidinone + NADPH + H+
1-azabicyclo[2.2.2]octan-3-ol + NADP+
show the reaction diagram
3-quinuclidinone + NADPH + H+
quinuclidin-3-ol + NADP+
show the reaction diagram
4-chlor-1-methylpiperidine + NADPH + H+
? + NADP+
show the reaction diagram
-
-
-
?
4-chloro-1-methylpiperidine + NADPH + H+
? + NADP+
show the reaction diagram
moderate activity
-
-
?
4-ethylcyclohexanone + NADPH
4-ethylcyclohexanol + NADP+
show the reaction diagram
4-ethylcyclohexanone + NADPH + H+
4-ethylcyclohexanol + NADP+
show the reaction diagram
4-methylcyclohexanone + NADPH
4-methylcyclohexanol + NADP+
show the reaction diagram
4-methylcyclohexanone + NADPH + H+
4-methylcyclohexanol + NADP+
show the reaction diagram
4-piperidone + NADPH + H+
4-hydroxypiperidin + NADP+
show the reaction diagram
very low activity
-
-
?
4-piperidone + NADPH + H+
? + NADP+
show the reaction diagram
-
-
-
?
4-tetrahydro-thiopyranone + NADPH
?
show the reaction diagram
-
83% of the reaction velocity with tropinone
-
-
?
7-hydroxytropinone + NADPH
7-hydroxytropan-3-ol + NADP+
show the reaction diagram
8-thiabicyclo(3,2,1)octane-3-one + NADPH
8-thiabicyclo(3,2,1)octane-3-ol + NADP+
show the reaction diagram
-
-
-
-
?
8-thiabicyclo[3.2.1]octan-3-one + NADPH
?
show the reaction diagram
exo-6-hydroxytropinone + NADPH + H+
? + NADP+
show the reaction diagram
N-(2-fluoroethyl)nortropinone + NADPH
N-(2-fluoroethyl)nortropan-3-ol + NADP+
show the reaction diagram
N-isopropylnortropinone + NADPH
N-isopropylnortropan-3-ol + NADP+
show the reaction diagram
N-methyl-4-pieridinone + NADPH
N-methyl-1-piperidinol + NADP+
show the reaction diagram
-
13% of the reaction velocity with tropinone
-
-
?
N-methyl-4-piperidinone + NADPH
N-methyl-1-piperidinol + NADP+
show the reaction diagram
-
180% of the reaction velocity with tropinone
-
-
?
N-methyl-4-piperidone + NADPH
1-methylpiperidin-4-ol + NADP+
show the reaction diagram
N-methyl-4-piperidone + NADPH + H+
1-methylpiperidin-4-ol + NADP+
show the reaction diagram
low activity
-
-
?
N-methyl-4-piperidone + NADPH + H+
? + NADP+
show the reaction diagram
-
-
-
?
N-methylpiperidine + NADPH + H+
? + NADP+
show the reaction diagram
N-propyl-4-piperidinone + NADPH
N-propylpiperidinol + NADP+
show the reaction diagram
-
78% of the reaction velocity with tropinone
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-
?
N-propyl-4-piperidone + NADPH
1-propylpiperidin-4-ol + NADP+
show the reaction diagram
-
-
-
-
?
nortropine + NADP+
nortropinone + NADPH
show the reaction diagram
quinuclidinone + NADPH
?
show the reaction diagram
scopine + NADP+
scopinone + NADPH
show the reaction diagram
-
-
-
-
?
tetrahydro-4H-thiopyran-4-one + NADPH + H+
? + NADP+
show the reaction diagram
tropine + NADP+
tropinone + NADPH
show the reaction diagram
tropine + NADP+
tropinone + NADPH + H+
show the reaction diagram
tropinone + NADPH + H+
pseudotropine + NADP+
show the reaction diagram
tropinone + NADPH + H+
tropine + NADP+
show the reaction diagram
tropinone + NADPH + H+
tropine + NADPH + H+
show the reaction diagram
the in vitro reaction kinetics predominantly favour the reaction direction of tropinone reduction
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r
additional information
?
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NATURAL SUBSTRATES
NATURAL PRODUCTS
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate) hide
LITERATURE
(Substrate)
COMMENTARY
(Product) hide
LITERATURE
(Product)
REVERSIBILITY
r=reversible
ir=irreversible
?=not specified
tropine + NADP+
tropinone + NADPH
show the reaction diagram
tropinone + NADPH + H+
pseudotropine + NADP+
show the reaction diagram
tropinone + NADPH + H+
tropine + NADP+
show the reaction diagram
additional information
?
-
COFACTOR
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
NADH
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lower affinity than with NADPH
NADP+
additional information
-
METALS and IONS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
Mg2+
slightly activating
Na+
slightly activating
additional information
INHIBITORS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
8-thiabicyclo(3,2,1)octane-3-one
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complete inhibition at 4 mM
Ca2+
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0-15% inactivation at 1 mM
Cd2+
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26-43% inactivation at 1 mM
Co2+
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0-15% inactivation at 1 mM
Cu2+
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99% inactivation at 1 mM
diethyl dicarbonate
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complete inhibition at 0.1 mM
Fe2+
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0-15% inactivation at 1 mM
Fe3+
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0-15% inactivation at 1 mM
Hg2+
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99% inactivation at 1 mM
K+
slight inhibitory effect at 5 mM
methyl jasmonate
inhibits expression of TRI in hairy roots
Mg2+
-
0-15% inactivation at 1 mM
Mn2+
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0-15% inactivation at 1 mM
Na+
slight inhibitory effect at 5 mM
NH4+
slight inhibitory effect at 5 mM
Ni2+
-
0-15% inactivation at 1 mM
p-chloromercuribenzoate
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strong inhibition at 0.1 and 1.0 mM
p-hydroxymercuribenzoate
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14% inhibition at 0.01 mM, 56% inhibition at 0.1 mM, 100% inhibition at 1.0 mM
Zn2+
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0-15% inactivation at 1 mM
additional information
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not inhibited by EDTA and iodoacetamide
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ACTIVATING COMPOUND
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
additional information
methyl jasmonate can enhance expression of TRI, with weak effect for TRI. TRI is induced weakly in all tissues
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KM VALUE [mM]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.004 - 2.11
3-methylcyclohexanone
0.167 - 5.17
3-quinuclidinone
0.003
4-ethylcyclohexanone
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-
0.001 - 8.71
4-methylcyclohexanone
0.003
8-thiabicyclo(3,2,1)octane-3-one
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-
0.231
N-Methyl-4-piperidone
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-
1.74
N-methylpiperidine
recombinant enzyme, pH 6.7, 30°C
-
10
NADH
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-
0.013 - 0.208
NADP+
0.00043 - 0.127
NADPH
0.073 - 2
nortropine
3.03
Nortropinone
-
-
0.91
Scopine
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-
0.006 - 114.9
Tropine
0.775 - 5.61
tropinone
additional information
additional information
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TURNOVER NUMBER [1/s]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
8.97
3-methylcyclohexanone
recombinant enzyme, pH 6.7, 30°C
0.54
3-quinuclidinone
pH 9.6, 22°C, recombinant His-tagged enzyme
4.67
4-methylcyclohexanone
pH 6.4, 22°C, recombinant His-tagged enzyme
9.23
N-methylpiperidine
recombinant enzyme, pH 6.7, 30°C
-
0.54 - 2.94
NADP+
6.76 - 33.34
NADPH
1.67 - 5.69
Tropine
2.4 - 25.6
tropinone
kcat/KM VALUE [1/mMs-1]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
5.17
3-methylcyclohexanone
recombinant enzyme, pH 6.7, 30°C
0.1045 - 22.18
3-quinuclidinone
0.0032 - 10.15
4-methylcyclohexanone
4.38
N-methylpiperidine
recombinant enzyme, pH 6.7, 30°C
-
0.559 - 14
NADP+
53 - 77540
NADPH
0.014 - 10.16
Tropine
0.00094 - 11.53
tropinone
SPECIFIC ACTIVITY [µmol/min/mg]
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
0.316
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crude extract
0.6
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tropinone
10.2
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tropinone
10.8
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tropinone
15
-
tropinone, strain Hn11
45
-
tropinone
54
Physalis edulis
-
tropinone
63.82
-
purified enzyme
additional information
pH OPTIMUM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
6.4
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reduction reaction
6.6
; tropinone reduction
6.8 - 8
6.8
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tropinone reduction
9.5
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tropine oxidation
9.6
tropine oxidation reaction
pH RANGE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
6.1 - 7
narrow pH range
additional information
TEMPERATURE OPTIMUM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
pI VALUE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
6.12
sequence calculation
6.45
sequence analysis
SOURCE TISSUE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
SOURCE
low enzyme level, all developmental stages
Manually annotated by BRENDA team
high enzyme level
Manually annotated by BRENDA team
additional information
MOLECULAR WEIGHT
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
29340
x * 29340, sequence calculation
29460
sequence analysis
30000
-
SDS-PAGE
56000
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gel filtration
58000
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gel filtration
115000
-
gel filtration
SUBUNITS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
homodimer
tetramer
additional information
Crystallization/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
hanging-drop vapor diffusion at 20°C
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pH STABILITY
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
6 - 10.5
-
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347967
TEMPERATURE STABILITY
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
4
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loss of 65% activity after 60 hours in crude extracts; loss of 90% activity of the purified enzyme after 10 hours, presence of 10% ethanol during the purification procedure
50 - 80
purified recombinant His-tagged enzyme, pH 6.6, 30 min, over 92% activity remaining at up to 50°C, 30% remaining at 60°C, 7% at 70°C, complete inactivation occurs at 80°C
50
purified recombinant enzyme, 30 min, over 92% of maximal activity remaining
50 - 60
purified recombinant enzyme, retains about 75% of maximal catalytic activity at up to 50°C, 4.27% activity remaining on incubation at 60°C
75
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immediate thermal denaturation
80
purified recombinant enzyme, 30 min, inactivation
STORAGE STABILITY
ORGANISM
UNIPROT
LITERATURE
-18°C, 50% glycerol, 3 weeks
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4°C, 0.46 mg protein/ml, complete inactivation of enzyme activity over night
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4°C, 2.3 mg protein/ml, 2 days, complete inactivation of enzyme activity
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4°C, 23 mg protein/ml, 9 days, complete inactivation of enzyme activity
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4°C, NADPH, NADP+ and glycerol enhance stability
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Purification/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
recombinant His-tagged enzyme from Escherichia coli strain BL21(DE3) by nickel affinity chromatography
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recombinant His-tagged enzyme from Escherichia coli strain Rosetta by nickel affinity chromatography
recombinant His6-tagged enzyme from Escherichia coli strain BL21(DE3) by affinity chromatography and gel filtration
recombinant His6-tagged enzyme from Escherichia coli strain BL21(DE3) by nickel affinity chromatography and gel filtration, followed by ultrafiltration
-
recombinant His6-tagged enzyme from Escherichia coli strain BL21(DE3) by nickel affinity chromatography; recombinant His-tagged enzyme from Escherichia coli strain BL21 (DE3) by nickel affinity chromatography
wild-type and recombinant enzymes from Atropa belladonna root cultures by ammonium sulfate fractionation
Cloned/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
cDNAs encoding two enzymes of tropane-alkaloid biosynthesis, tropinone reductase I and hyoscyamine-6beta-hydroxylase are simultaneously introduced into Nicotiana tabacum using particle bombardment and expressed under the control of the CaMV 35S promoter. The expression leads to the formation of unexpected substances, e.g. acetyltropine. Leaves of transgenic plants show in most cases higher nicotine content than leaves of control plants. In addition nicotine related compounds such as anatabine, nornicotine, bipyridine, anabasine, and myosmine are identified in transgenic tobacco lines and are below detection limit in wild-type plants
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gene DnTR1, sequence comparisons and unrooted phylogenetic tree, recombinant expression of His6-tagged enzyme in Escherichia coli strain BL21(DE3), realtime PCR enzyme expression analysis
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gene tr, DNA and amino acid sequence determination and analysis, sequence comparison
gene TR-I from roots, DNA and amino acid sequence determination and analysis, sequence comparisons and phylogenetic analysis and tree, recombinant functional overexpression of His6-tagged enzyme in Escherichia coli strain BL21(DE3)
gene TR1, enzyme overexpression via leaves transformation with Agrobacterium tumefaciens AGL0, quantitative PCR enzyme expression analysis
gene TR1, expression in Atropa belladonna root cultures, derived from transfected leaves using the transformation system via Agrobacterium rhizogenes strain 15834
gene trI, DNA and amino acid sequence determination and analysis, expression as His-tagged enzyme in Escherichia coli strain BL21(DE3)
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gene TRI, DNA and amino acid sequence determination and analysis, sequence comparisons and phylogenetic analysis and tree, functional recombinant overexpression of His-tagged enzyme in Escherichia coli strain Rosetta
gene TRI, isolated from aerial tissue, DNA and amino acid sequence determination and analysis, sequence comparisons and phylogenetic analysis, overexpression of the His-tagged enzyme in Escherichia coli strain BL21 (DE3); gene WcTR-I, from leaves, DNA and amino acid sequence determination and analysis, sequence comparisons, phylogenetic analysis and tree, recombinant expression of His6-tagged enzyme in Escherichia coli strain BL21(DE3)
gene TRI, sequence comparisons
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sixteen different peptide segment exchanges with tropinone reductase II
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TRI-transformed hairy root lines. Full-length fragment of TRI cDNA insert constructed into the pBI121 expression cassette in place of GUS gene. The vector pCAMBIA1304+ contains the TRI gene under control of CaMV35S promoter. Disarmed Agrobacterium tumefaciens strain C58C1 harboring both Agrobacterium rhizogenes Ri plasmid pRiA4 and pCAMBIA1304+, containing a single TRI gene, used for plant transformation
wild-type and recombinant enzymes from Atropa belladonna root cultures by ammonium sulfate fractionation
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EXPRESSION
ORGANISM
UNIPROT
LITERATURE
salicylic acid and sodium nitroprusside treatments do not affect the enzyme expression
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the enzyme expression is upregulated by methyl jasmonate, but not by salicylate and NO
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the enzyme-encoding TR-I gene expression is upregulated on exposure to signal molecules, i.e. methyl jasmonate and salicylic acid, and on mechanical injury/wounding
the expression of DnTR1 mRNA is enhanced 9.5times by treatment of methyl jasmonate after 24 h, expression profile of DnTR1
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ENGINEERING
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
A160S
-
higher Km for tropinone that wild type enzyme
H112F
-
higher Km for tropinone that wild type enzyme
H112Y
-
higher Km for tropinone that wild type enzyme
V168E
-
lower Km for tropinone that wild type enzyme
additional information
APPLICATION
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
synthesis