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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reduction
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-
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PATHWAY
BRENDA Link
KEGG Link
MetaCyc Link
hyoscyamine and scopolamine biosynthesis
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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
-
-
-
Manually annotated by BRENDA team
Brugmansia sp.
candida x aurea hybrid
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-
Manually annotated by BRENDA team
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-
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Manually annotated by BRENDA team
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-
-
Manually annotated by BRENDA team
Hyoscyamus bohemicus
-
-
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Manually annotated by BRENDA team
Hyoscyamus canariensis
-
-
-
Manually annotated by BRENDA team
strain Hn and 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
-
-
-
Manually annotated by BRENDA team
no activity in Physalis alkekengi
-
-
-
Manually annotated by BRENDA team
Physalis edulis
-
-
-
Manually annotated by BRENDA team
AT3
-
-
Manually annotated by BRENDA team
AT3
-
-
Manually annotated by BRENDA team
Scopolia atropoides
-
-
-
Manually annotated by BRENDA team
gene trI
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-
Manually annotated by BRENDA team
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UniProt
Manually annotated by BRENDA team
GENERAL INFORMATION
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
evolution
tropinone reductase TR-I belongs to the short chain dehydrogenase/reductase family, SDR, of enzymes and has a YSASK as the signature YXXXK motif of SDRs, catalytic tetrade comprises N, S, Y, and K residues, overview
metabolism
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+
? + NADP+
show the reaction diagram
-
-
-
?
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
-
-
?
3-methylcyclohexanone + NADPH
3-methylcyclohexanol + NADP+
show the reaction diagram
3-methylcyclohexanone + NADPH + H+
? + 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-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+
? + 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+
? + 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
-
-
?
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
in vitro reaction kinetics show that the enzyme predominantly favours the reverse reaction
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-
r
tropinone + NADPH + H+
pseudotropine + NADP+
show the reaction diagram
tropinone + NADPH + H+
tropine + NADP+
show the reaction diagram
additional information
?
-
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
-
lower affinity than with NADPH
NADP+
additional information
-
no activity with NAD+
-
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+
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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+
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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
-
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
3-methylcyclohexanone
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-
1.81
3-quinuclidinone
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-
0.003
4-ethylcyclohexanone
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-
0.001
4-methylcyclohexanone
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-
0.003
8-thiabicyclo(3,2,1)octane-3-one
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-
0.231
N-Methyl-4-piperidone
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-
10
NADH
-
-
0.013 - 0.208
NADP+
0.011 - 0.126
NADPH
0.073 - 2
nortropine
3.03
Nortropinone
-
-
0.91
Scopine
-
-
0.006 - 26.31
Tropine
0.775 - 1.451
tropinone
TURNOVER NUMBER [1/s]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
2.94
NADP+
Withania coagulans
L7QI79
pH 6.6, 30C, recombinant enzyme
6.76
NADPH
Withania coagulans
L7QI79
pH 6.6, 30C, recombinant enzyme
1.87
Tropine
Withania coagulans
L7QI79
pH 6.6, 30C, recombinant enzyme
16.74 - 25.6
tropinone
kcat/KM VALUE [1/mMs-1]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
14
NADP+
Withania coagulans
L7QI79
pH 6.6, 30C, recombinant enzyme
10
53
NADPH
Withania coagulans
L7QI79
pH 6.6, 30C, recombinant enzyme
5
0.071
Tropine
Withania coagulans
L7QI79
pH 6.6, 30C, recombinant enzyme
3848
11.53
tropinone
Withania coagulans
L7QI79
pH 6.6, 30C, recombinant enzyme
1567
SPECIFIC ACTIVITY [µmol/min/mg]
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
0.316
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crude extract
0.6
-
tropinone
10.2
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tropinone
10.8
-
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
6.8
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tropinone reduction
9.5
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tropine oxidation
9.9
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oxidation reaction
pH RANGE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
6.1 - 7
narrow pH range
TEMPERATURE OPTIMUM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
pI VALUE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
6.45
sequence analysis
SOURCE TISSUE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
SOURCE
transcript level of TRI is low
Manually annotated by BRENDA team
MOLECULAR WEIGHT
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
28000
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SDS-PAGE
29460
sequence analysis
30000
-
SDS-PAGE
56000
-
gel filtration
58000
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gel filtration
115000
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gel filtration
SUBUNITS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
?
x * 29340, sequence calculation
tetramer
additional information
Crystallization/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
hanging-drop vapor diffusion at 20C
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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
75
-
immediate thermal denaturation
80
purified recombinant enzyme, 30 min, inactivation
STORAGE STABILITY
ORGANISM
UNIPROT
LITERATURE
-18C, 50% glycerol, 3 weeks
-
4C, 0.46 mg protein/ml, complete inactivation of enzyme activity over night
-
4C, 2.3 mg protein/ml, 2 days, complete inactivation of enzyme activity
-
4C, 23 mg protein/ml, 9 days, complete inactivation of enzyme activity
-
4C, 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
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 tr, DNA and amino acid sequence determination and analysis, sequence comparison
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, 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)
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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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