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1-methylpyrrolidine + NADPH + H+
? + NADP+
-
-
-
?
1-propyl-4-piperidone + NADPH + H+
1-propylpiperidin-4-ol + NADP+
low activity
-
-
?
1-propyl-4-piperidone + NADPH + H+
? + NADP+
-
-
-
?
2-pyrrolidone + NADPH + H+
2-hydroxypyrrolidine + NADP+
very low activity
-
-
?
2-pyrrolidone + NADPH + H+
? + NADP+
-
-
-
?
3-methyl-cyclohexanone + NADPH
3-methylcyclohexanol + NADP+
-
85% of the reaction velocity with tropinone
-
-
?
3-methylcyclohexanone + NADPH
3-methylcyclohexanol + NADP+
3-methylcyclohexanone + NADPH + H+
3-methylcyclohexanol + NADP+
3-methylcyclohexanone + NADPH + H+
? + NADP+
-
-
-
?
3-quinuclidinone + NADPH + H+
1-azabicyclo[2.2.2]octan-3-ol + NADP+
3-quinuclidinone + NADPH + H+
quinuclidin-3-ol + NADP+
4-chlor-1-methylpiperidine + NADPH + H+
? + NADP+
-
-
-
?
4-chloro-1-methylpiperidine + NADPH + H+
? + NADP+
moderate activity
-
-
?
4-ethylcyclohexanone + NADPH
4-ethylcyclohexanol + NADP+
4-ethylcyclohexanone + NADPH + H+
4-ethylcyclohexanol + NADP+
4-methylcyclohexanone + NADPH
4-methylcyclohexanol + NADP+
4-methylcyclohexanone + NADPH + H+
4-methylcyclohexanol + NADP+
4-piperidone + NADPH + H+
4-hydroxypiperidin + NADP+
very low activity
-
-
?
4-piperidone + NADPH + H+
? + NADP+
-
-
-
?
4-tetrahydro-thiopyranone + NADPH
?
-
83% of the reaction velocity with tropinone
-
-
?
7-hydroxytropinone + NADPH
7-hydroxytropan-3-ol + NADP+
8-thiabicyclo(3,2,1)octane-3-one + NADPH
8-thiabicyclo(3,2,1)octane-3-ol + NADP+
-
-
-
-
?
8-thiabicyclo[3.2.1]octan-3-one + NADPH
?
exo-6-hydroxytropinone + NADPH + H+
? + NADP+
N-(2-fluoroethyl)nortropinone + NADPH
N-(2-fluoroethyl)nortropan-3-ol + NADP+
N-isopropylnortropinone + NADPH
N-isopropylnortropan-3-ol + NADP+
N-methyl-4-piperidinone + NADPH
N-methyl-1-piperidinol + NADP+
-
180% of the reaction velocity with tropinone
-
-
?
N-methyl-4-piperidinone + NADPH + H+
N-methyl-1-piperidinol + NADP+
-
13% of the reaction velocity with tropinone
-
-
?
N-methyl-4-piperidone + NADPH
1-methylpiperidin-4-ol + NADP+
N-methyl-4-piperidone + NADPH + H+
1-methylpiperidin-4-ol + NADP+
low activity
-
-
?
N-methyl-4-piperidone + NADPH + H+
? + NADP+
-
-
-
?
N-methylpiperidine + NADPH + H+
? + NADP+
N-propyl-4-piperidinone + NADPH
N-propylpiperidinol + NADP+
-
78% of the reaction velocity with tropinone
-
-
?
N-propyl-4-piperidone + NADPH
1-propylpiperidin-4-ol + NADP+
-
-
-
-
?
nortropine + NADP+
nortropinone + NADPH
scopine + NADP+
scopinone + NADPH
-
-
-
-
?
tetrahydro-4H-thiopyran-4-one + NADPH + H+
? + NADP+
tropine + NADP+
tropinone + NADPH
tropine + NADP+
tropinone + NADPH + H+
tropinone + NADH + H+
tropine + NAD+
-
-
-
-
r
tropinone + NADPH + H+
pseudotropine + NADP+
tropinone + NADPH + H+
tropine + NADP+
additional information
?
-
3-methylcyclohexanone + NADPH
3-methylcyclohexanol + NADP+
Brugmansia sp.
-
-
-
-
?
3-methylcyclohexanone + NADPH
3-methylcyclohexanol + NADP+
-
-
-
-
?
3-methylcyclohexanone + NADPH
3-methylcyclohexanol + NADP+
-
-
-
-
?
3-methylcyclohexanone + NADPH
3-methylcyclohexanol + NADP+
-
-
-
-
?
3-methylcyclohexanone + NADPH + H+
3-methylcyclohexanol + NADP+
-
-
-
?
3-methylcyclohexanone + NADPH + H+
3-methylcyclohexanol + NADP+
-
-
-
?
3-quinuclidinone + NADPH + H+
1-azabicyclo[2.2.2]octan-3-ol + NADP+
-
-
-
r
3-quinuclidinone + NADPH + H+
1-azabicyclo[2.2.2]octan-3-ol + NADP+
-
-
-
r
3-quinuclidinone + NADPH + H+
1-azabicyclo[2.2.2]octan-3-ol + NADP+
-
-
-
r
3-quinuclidinone + NADPH + H+
1-azabicyclo[2.2.2]octan-3-ol + NADP+
-
-
-
-
r
3-quinuclidinone + NADPH + H+
quinuclidin-3-ol + NADP+
Brugmansia sp.
-
-
-
-
?
3-quinuclidinone + NADPH + H+
quinuclidin-3-ol + NADP+
-
-
-
-
?
3-quinuclidinone + NADPH + H+
quinuclidin-3-ol + NADP+
-
-
-
-
?
4-ethylcyclohexanone + NADPH
4-ethylcyclohexanol + NADP+
Brugmansia sp.
-
-
-
-
?
4-ethylcyclohexanone + NADPH
4-ethylcyclohexanol + NADP+
-
-
-
-
?
4-ethylcyclohexanone + NADPH
4-ethylcyclohexanol + NADP+
-
41% of the reaction velocity with tropinone
-
-
?
4-ethylcyclohexanone + NADPH
4-ethylcyclohexanol + NADP+
-
-
-
-
?
4-ethylcyclohexanone + NADPH
4-ethylcyclohexanol + NADP+
-
-
-
-
?
4-ethylcyclohexanone + NADPH
4-ethylcyclohexanol + NADP+
-
107% of the reaction velocity with tropinone
-
-
?
4-ethylcyclohexanone + NADPH
4-ethylcyclohexanol + NADP+
-
-
-
-
?
4-ethylcyclohexanone + NADPH + H+
4-ethylcyclohexanol + NADP+
-
-
-
?
4-ethylcyclohexanone + NADPH + H+
4-ethylcyclohexanol + NADP+
low activity
-
-
?
4-methylcyclohexanone + NADPH
4-methylcyclohexanol + NADP+
Brugmansia sp.
-
-
-
-
?
4-methylcyclohexanone + NADPH
4-methylcyclohexanol + NADP+
-
-
-
-
?
4-methylcyclohexanone + NADPH
4-methylcyclohexanol + NADP+
-
-
-
-
?
4-methylcyclohexanone + NADPH
4-methylcyclohexanol + NADP+
-
-
-
-
?
4-methylcyclohexanone + NADPH
4-methylcyclohexanol + NADP+
-
-
-
-
?
4-methylcyclohexanone + NADPH + H+
4-methylcyclohexanol + NADP+
-
-
-
r
4-methylcyclohexanone + NADPH + H+
4-methylcyclohexanol + NADP+
-
-
-
r
4-methylcyclohexanone + NADPH + H+
4-methylcyclohexanol + NADP+
-
-
-
r
4-methylcyclohexanone + NADPH + H+
4-methylcyclohexanol + NADP+
-
-
-
-
r
4-methylcyclohexanone + NADPH + H+
4-methylcyclohexanol + NADP+
-
-
-
?
4-methylcyclohexanone + NADPH + H+
4-methylcyclohexanol + NADP+
low activity
-
-
?
7-hydroxytropinone + NADPH
7-hydroxytropan-3-ol + NADP+
Brugmansia sp.
-
-
-
-
?
7-hydroxytropinone + NADPH
7-hydroxytropan-3-ol + NADP+
-
-
-
-
?
8-thiabicyclo[3.2.1]octan-3-one + NADPH
?
-
35% of the reaction velocity with tropinone
-
-
?
8-thiabicyclo[3.2.1]octan-3-one + NADPH
?
-
40% of the reaction velocity with tropinone
-
-
?
exo-6-hydroxytropinone + NADPH + H+
? + NADP+
-
-
-
?
exo-6-hydroxytropinone + NADPH + H+
? + NADP+
low activity
-
-
?
N-(2-fluoroethyl)nortropinone + NADPH
N-(2-fluoroethyl)nortropan-3-ol + NADP+
Brugmansia sp.
-
-
-
-
?
N-(2-fluoroethyl)nortropinone + NADPH
N-(2-fluoroethyl)nortropan-3-ol + NADP+
-
-
-
-
?
N-isopropylnortropinone + NADPH
N-isopropylnortropan-3-ol + NADP+
Brugmansia sp.
-
-
-
-
?
N-isopropylnortropinone + NADPH
N-isopropylnortropan-3-ol + NADP+
-
-
-
-
?
N-methyl-4-piperidone + NADPH
1-methylpiperidin-4-ol + NADP+
Brugmansia sp.
-
-
-
-
?
N-methyl-4-piperidone + NADPH
1-methylpiperidin-4-ol + NADP+
-
-
-
-
?
N-methyl-4-piperidone + NADPH
1-methylpiperidin-4-ol + NADP+
-
-
-
-
?
N-methyl-4-piperidone + NADPH
1-methylpiperidin-4-ol + NADP+
-
-
-
-
?
N-methyl-4-piperidone + NADPH
1-methylpiperidin-4-ol + NADP+
-
-
-
-
?
N-methylpiperidine + NADPH + H+
? + NADP+
-
-
-
?
N-methylpiperidine + NADPH + H+
? + NADP+
-
-
-
?
nortropine + NADP+
nortropinone + NADPH
Brugmansia sp.
-
-
-
r
nortropine + NADP+
nortropinone + NADPH
-
-
-
?
nortropine + NADP+
nortropinone + NADPH
-
-
-
?
nortropine + NADP+
nortropinone + NADPH
-
-
-
?
nortropine + NADP+
nortropinone + NADPH
-
-
-
-
?
nortropine + NADP+
nortropinone + NADPH
-
-
-
-
?
quinuclidinone + NADPH
?
-
80% of the reaction velocity with tropinone
-
-
?
quinuclidinone + NADPH
?
-
136% of the reaction velocity with tropinone
-
-
?
tetrahydro-4H-thiopyran-4-one + NADPH + H+
? + NADP+
-
-
-
?
tetrahydro-4H-thiopyran-4-one + NADPH + H+
? + NADP+
moderate activity
-
-
?
tropine + NADP+
tropinone + NADPH
Brugmansia sp.
-
-
-
r
tropine + NADP+
tropinone + NADPH
-
-
-
?
tropine + NADP+
tropinone + NADPH
-
-
-
?
tropine + NADP+
tropinone + NADPH
-
-
-
r
tropine + NADP+
tropinone + NADPH
-
-
-
r
tropine + NADP+
tropinone + NADPH
-
-
-
r
tropine + NADP+
tropinone + NADPH
-
last step in biosynthesis of tropine
-
-
r
tropine + NADP+
tropinone + NADPH
-
-
-
r
tropine + NADP+
tropinone + NADPH
-
-
-
r
tropine + NADP+
tropinone + NADPH
-
-
-
r
tropine + NADP+
tropinone + NADPH
-
-
-
r
tropine + NADP+
tropinone + NADPH
-
role in the pathway for tropine catabolism
-
-
r
tropine + NADP+
tropinone + NADPH
-
-
-
r
tropine + NADP+
tropinone + NADPH
-
role in the pathway for tropine catabolism
-
-
r
tropine + NADP+
tropinone + NADPH + H+
-
-
-
r
tropine + NADP+
tropinone + NADPH + H+
-
-
-
r
tropine + NADP+
tropinone + NADPH + H+
-
-
-
r
tropine + NADP+
tropinone + NADPH + H+
-
-
-
r
tropine + NADP+
tropinone + NADPH + H+
in vitro reaction kinetics show that the enzyme predominantly favours the reverse reaction
-
-
r
tropine + NADP+
tropinone + NADPH + H+
catalytic kinetics of the enzyme favour the forward reaction, tropine formation
-
-
r
tropinone + NADPH + H+
pseudotropine + NADP+
-
tropinone reductase II
-
-
?
tropinone + NADPH + H+
pseudotropine + NADP+
-
tropinone reductase II
-
-
?
tropinone + NADPH + H+
tropine + NADP+
-
-
-
?
tropinone + NADPH + H+
tropine + NADP+
-
-
-
-
?
tropinone + NADPH + H+
tropine + NADP+
-
tropine is the precursor of the tropane alkaloids hyoscyamine and scopolamine
-
-
?
tropinone + NADPH + H+
tropine + NADP+
-
-
-
r
tropinone + NADPH + H+
tropine + NADP+
-
-
-
r
tropinone + NADPH + H+
tropine + NADP+
reaction of tropinone reductase I, EC 1.1.1.206, tropane alkaloid biosynthesis, overview
leading to formation of tropane alkaloids
-
?
tropinone + NADPH + H+
tropine + NADP+
reaction of tropinone reductase I, EC 1.1.1.206
-
-
?
tropinone + NADPH + H+
tropine + NADP+
-
-
-
-
r
tropinone + NADPH + H+
tropine + NADP+
-
-
-
?
tropinone + NADPH + H+
tropine + NADP+
-
-
-
r
tropinone + NADPH + H+
tropine + NADP+
-
tropine is the precursor of the tropane alkaloids hyoscyamine and scopolamine
-
-
r
tropinone + NADPH + H+
tropine + NADP+
tropine is the precursor of the tropane alkaloids hyoscyamine and scopolamine
-
-
?
tropinone + NADPH + H+
tropine + NADP+
-
-
-
r
tropinone + NADPH + H+
tropine + NADP+
-
-
-
-
r
tropinone + NADPH + H+
tropine + NADP+
-
-
-
-
?
tropinone + NADPH + H+
tropine + NADP+
-
tropine is the precursor of the tropane alkaloids hyoscyamine and scopolamine
-
-
?
tropinone + NADPH + H+
tropine + NADP+
-
-
-
-
?
tropinone + NADPH + H+
tropine + NADP+
-
tropine is the precursor of the tropane alkaloids hyoscyamine and scopolamine
-
-
?
tropinone + NADPH + H+
tropine + NADP+
-
-
-
-
?
tropinone + NADPH + H+
tropine + NADP+
-
tropine is the precursor of the tropane alkaloids hyoscyamine and scopolamine
-
-
?
tropinone + NADPH + H+
tropine + NADP+
-
-
-
-
r
tropinone + NADPH + H+
tropine + NADP+
-
tropine is the precursor of the tropane alkaloids hyoscyamine and scopolamine
-
-
r
tropinone + NADPH + H+
tropine + NADP+
-
-
-
?
tropinone + NADPH + H+
tropine + NADP+
direction of biosynthesis
-
-
r
tropinone + NADPH + H+
tropine + NADP+
stereospecific reduction of the 3-carbonyl group of tropinone to hydroxyl group (tropine) with distinct stereospecific configuration, product identification by GC-MS analysis
-
-
r
tropinone + NADPH + H+
tropine + NADP+
Scopolia atropoides
-
-
-
-
?
tropinone + NADPH + H+
tropine + NADP+
Scopolia atropoides
-
tropine is the precursor of the tropane alkaloids hyoscyamine and scopolamine
-
-
?
tropinone + NADPH + H+
tropine + NADP+
-
-
-
-
r
tropinone + NADPH + H+
tropine + NADP+
-
the enzyme is involved in tropane alkaloid biosynthesis, e.g. of (S)-hyoscyamine, overview
-
-
r
tropinone + NADPH + H+
tropine + NADP+
-
-
-
r
tropinone + NADPH + H+
tropine + NADP+
Solanum tuberosum tropinone reductase I reduces tropinone in vivo
-
-
r
tropinone + NADPH + H+
tropine + NADP+
best substrate
-
-
r
tropinone + NADPH + H+
tropine + NADP+
preferred substrate
-
-
r
tropinone + NADPH + H+
tropine + NADP+
the reaction direction of tropinone reduction is predominantly operational in planta
-
-
r
tropinone + NADPH + H+
tropine + NADP+
the in vitro reaction kinetics predominantly favour the reaction direction of tropinone reduction
-
-
r
tropinone + NADPH + H+
tropine + NADP+
-
-
-
r
additional information
?
-
significant increase of tropane alkaloids after TRI single gene transformation in Anisodus acutangulus
-
-
?
additional information
?
-
at pH 6.4, the non-ionizable substrate 4-methylcyclohexanone is uncharged, whereas the nitrogen-containing substrates tropinone and 3-quinuclidinone are positively charged. Enzyme BaTRI exhibits significantly higher apparent affinity for 4-methylcyclohexanone than tropinone and 3-quinuclidinone, of which only the deprotonated fractions can be bound by BaTRI
-
-
?
additional information
?
-
-
at pH 6.4, the non-ionizable substrate 4-methylcyclohexanone is uncharged, whereas the nitrogen-containing substrates tropinone and 3-quinuclidinone are positively charged. Enzyme BaTRI exhibits significantly higher apparent affinity for 4-methylcyclohexanone than tropinone and 3-quinuclidinone, of which only the deprotonated fractions can be bound by BaTRI
-
-
?
additional information
?
-
the bifunctional enzyme of Cochlearia officinalis is not stereospecific, in contrast to the Solanaceae species, and catalyzes both tropinone reductase reactions, a tyrosine residue in the active site of Cochlearia officinalis TR is responsible for binding and orientation of tropinone, overview
-
-
?
additional information
?
-
the enzyme shows broad substrate specificity, several synthetic ketones are accepted as substrates, with higher affinity and faster enzymatic turnover than observed for tropinone, overview
-
-
?
additional information
?
-
-
no activity with 3-methyl-cyclohexanone
-
-
?
additional information
?
-
-
no activity with N-propyl-4-pieridinone and 4-tetrahydro-thiopyranone
-
-
?
additional information
?
-
tropinone feeding experiments
-
-
?
additional information
?
-
-
tropinone feeding experiments
-
-
?
additional information
?
-
the enzyme TR-I has a wide substrate specificity but does not cover the substrates of other well-known plant SDR related to menthol metabolism
-
-
?
additional information
?
-
-
the enzyme TR-I has a wide substrate specificity but does not cover the substrates of other well-known plant SDR related to menthol metabolism
-
-
?
additional information
?
-
no activity by TR-I with 1-methyl-2-pyrrolidone
-
-
?
additional information
?
-
-
no activity by TR-I with 1-methyl-2-pyrrolidone
-
-
?
additional information
?
-
wide substrate specificity, overview. No activity with 1-methyl-2-pyrrolidone. The reverse reaction of tropine oxidation is highly specific and none of the tested alcohols can be oxidized with either NADP+ or NAD+ as cofactor
-
-
?
additional information
?
-
-
wide substrate specificity, overview. No activity with 1-methyl-2-pyrrolidone. The reverse reaction of tropine oxidation is highly specific and none of the tested alcohols can be oxidized with either NADP+ or NAD+ as cofactor
-
-
?
additional information
?
-
TLC and GC-MS analysis of substrates and products. The enzyme also shows comparatively efficient catalysis of NADPH-dependent reduction of cyclic ketones 3-methylcyclohexanone and N-methylpiperidine, substrate specificity, overview. No activity with 1-methyl-2-pyrrolidone
-
-
?
additional information
?
-
-
TLC and GC-MS analysis of substrates and products. The enzyme also shows comparatively efficient catalysis of NADPH-dependent reduction of cyclic ketones 3-methylcyclohexanone and N-methylpiperidine, substrate specificity, overview. No activity with 1-methyl-2-pyrrolidone
-
-
?
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0.004 - 2.11
3-methylcyclohexanone
0.167 - 5.17
3-quinuclidinone
0.003
4-ethylcyclohexanone
-
-
0.001 - 8.71
4-methylcyclohexanone
0.003
8-thiabicyclo(3,2,1)octane-3-one
-
-
0.231
N-Methyl-4-piperidone
-
-
1.74
N-methylpiperidine
recombinant enzyme, pH 6.7, 30°C
additional information
additional information
-
0.004
3-methylcyclohexanone
-
-
2.11
3-methylcyclohexanone
recombinant enzyme, pH 6.7, 30°C
0.167
3-quinuclidinone
pH 8.0, 25°C, recombinant His-tagged enzyme
1.81
3-quinuclidinone
-
-
5.17
3-quinuclidinone
pH 9.6, 22°C, recombinant His-tagged enzyme
0.001
4-methylcyclohexanone
-
-
0.46
4-methylcyclohexanone
pH 6.4, 22°C, recombinant His-tagged enzyme
8.71
4-methylcyclohexanone
pH 8.0, 25°C, recombinant His-tagged enzyme
0.013
NADP+
-
-
0.0962
NADP+
recombinant enzyme, pH 6.7, 30°C
0.208
NADP+
pH 6.6, 30°C, recombinant enzyme
0.208
NADP+
pH 6.6, 30°C, recombinant His-tagged enzyme
0.00043
NADPH
recombinant enzyme, pH 6.7, 30°C
0.126
NADPH
pH 6.6, 30°C, recombinant enzyme
0.127
NADPH
pH 6.6, 30°C, recombinant His-tagged enzyme
0.073
nortropine
-
-
0.006
Tropine
-
-
0.188
Tropine
pH 9.6, temperature not specified in the publication
0.34
Tropine
pH 9.6, 22°C
0.56
Tropine
pH 9.6, 22°C, recombinant His-tagged enzyme
26.31
Tropine
pH 6.6, 30°C, recombinant enzyme
26.31
Tropine
pH 6.6, 30°C, recombinant His-tagged enzyme
114.9
Tropine
recombinant enzyme, pH 6.7, 30°C
0.21
tropinone
pH 6.4, temperature not specified in the publication
0.52
tropinone
pH 6.4, 30°C
0.52
tropinone
pH 6.4, 30°C, enzyme TRI
1.27
tropinone
recombinant enzyme, pH 6.7, 30°C
1.451
tropinone
pH 6.6, 30°C, recombinant enzyme
1.451
tropinone
pH 6.6, 30°C, recombinant His-tagged enzyme
2.65
tropinone
pH 6.4, 22°C, recombinant His-tagged enzyme
4.18
tropinone
pH 6.4, 22°C
5.61
tropinone
pH 8.0, 25°C, recombinant His-tagged enzyme
40.9
tropinone
30°C, pH 6.4
additional information
additional information
Michaelis-Menten kinetics
-
additional information
additional information
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Michaelis-Menten kinetics
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additional information
additional information
Michaelis-Menten kinetics
-
additional information
additional information
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Michaelis-Menten kinetics
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additional information
additional information
Michaelis-Menten kinetics
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additional information
additional information
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Michaelis-Menten kinetics
-
additional information
additional information
Michaelis-Menten kinetics
-
additional information
additional information
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Michaelis-Menten kinetics
-
additional information
additional information
MichaelisMenten kinetics
-
additional information
additional information
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MichaelisMenten kinetics
-
additional information
additional information
the in vitro reaction kinetics predominantly favour the reaction direction of tropinone reduction, Michaelis-Menten kinetics
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additional information
additional information
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the in vitro reaction kinetics predominantly favour the reaction direction of tropinone reduction, Michaelis-Menten kinetics
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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
evolution
enzyme TRI belongs to the family of short chain dehydrogenases/reductases (SDRs) that catalyse NAD(P)(H)-dependent redox reactions
evolution
enzyme TRI belongs to the family of short chain dehydrogenases/reductases (SDRs) that catalyse NAD(P)(H)-dependent redox reactions
evolution
molecular evolution of WsTR-I, overview
evolution
the enzyme belongs to the short chain dehydrogenase/reductase (SDR) superfamily that is composed of a group of NAD(P)H-dependent oxidoreductases that typically consist of 250-350 amino acids. Tropinone reductases (TRs) are a group of the SDR superfamily, that use the NADPH as coenzyme to reduce tropinone DnTR1 also contains the sequence pattern G-X3-G-X-G in the cofactor binding motif and active site motif (S-N-K)
evolution
tropinone reductases (TRs) are small proteins belonging to the SDR (short chain dehydrogenase/reductase) family of enzymes. The enzyme's sequence contains the signature YXXXK motif of SDRs. Residues His112, Ala160, Val168, Ile223 and Phe226 are conserved in the TRs, and conserved at corresponding positions in WcTR-I, and involved in stereospecificity of the respective TR-Is. Tropane alkaloids might have evolved independently in plants, at least in Solanaceae and Erythroxylaceae
evolution
both PtTRI and PtTRII have a conserved NADPH-binding site with a typical sequence characterized by the GXXXGXG motif. There are also two conserved domains in the amino acid sequence: the NNAG domain that is unique to the short-chain dehydrogenase family and the S-Y-K structure which is unique to TRs
malfunction
-
effects of overexpression of putrescine N-methyltransferase (EC 2.1.1.53, Pmt) and hyoscyamine 6beta-hydroxylase (EC 1.14.11.11, H6h) in Hyoscyamus senecionis plants on TRI and TRII enzyme expression rates, plant growth rates, and alkaloids content, overview
malfunction
-
effects of overexpression of putrescine N-methyltransferase (EC 2.1.1.53, Pmt) and hyoscyamine 6beta-hydroxylase (EC 1.14.11.11, H6h) in Hyoscyamus senecionis plants on TRI and TRII enzyme expression rates, plant growth rates, and alkaloids content, overview
malfunction
-
effects of overexpression of putrescine N-methyltransferase (EC 2.1.1.53, Pmt) and hyoscyamine 6beta-hydroxylase (EC 1.14.11.11, H6h) in Hyoscyamus senecionis plants on TRI and TRII enzyme expression rates, plant growth rates, and alkaloids content, overview
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metabolism
the enzyme catalyzes a step intermediary enroute to biosynthesis of tropane esters of medicinal importance, i.e. hyoscyamine/scopolamine
metabolism
-
tropinone reductase II is part of biosynthesis of calystegines, overview. Hyoscyamine is the main tropane alkaloid of the leaf and root of Hyoscyamus muticus. Higher amounts of littorine as an intermediate compound in the pathway, and 3'-hydroxylittorine are accumulated in roots than in other organs
metabolism
-
tropinone reductase II is part of biosynthesis of calystegines, overview. Scopolamine is the main tropane alkaloid compound in Hyoscyamus senecionis leaves. Higher amounts of littorine as an intermediate compound in the pathway, and 3'-hydroxylittorine are accumulated in roots than in other organs
metabolism
enzymes TR-I and TR-II catalyze the conversion of tropinone into tropane alcohols (tropine and pseudotropine, respectively). The steps are intermediary enroute to biosynthesis of tropane esters of medicinal importance, hyoscyamine/scopolamine, and calystegins, respectively. The enzyme has a wide substrate specificity but does not cover the substrates of other plant SDR enzymes related to menthol metabolism. The leaf tissue expression of the enzyme with these catalytic features suggests physiologically much prodigal rate of operation of the tropane alkaloid pathway in the leaf tissue itself
metabolism
the enzyme catalyzes the NADPH-dependent tropinone to tropine conversion step in tropane metabolism, metabolic pathway of tropane alkaloid biosynthesis, overview
metabolism
tropinone reductases form a branch point in the pathway leading to tropine (TRI) and to pseudotropine (TRII) during the tropane alkaloid biosynthesis, overview. Enzyme TRI is involved in the formation of tropine, the preproduct of hyoscyamine, whereas enzyme TRII, EC 1.1.1.236, is responsible for the generation of pseudotropine
metabolism
two tropinone reductases (TRs) constitute an important branch point in the tropanalkaloid biosynthetic pathway. Tropinone reductase I or tropine-forming reductase, EC 1.1.1.206, reduces tropinone to tropine during tropanalkaloid biosynthesis, whereas tropinone reductase II, EC 1.1.1.236, reduces tropinone to pseudotropine, diverging metabolic flux to nortropane calystegine A3. TRI activity controls metabolic flux towards hyoscyamine and downstream tropanalkaloids' biosynthesis
metabolism
two tropinone reductases (TRs) constitute an important branch point in the tropanalkaloid biosynthetic pathway. Tropinone reductase I or tropine-forming reductase, EC 1.1.1.206, reduces tropinone to tropine during tropanalkaloid biosynthesis, whereas tropinone reductase II, EC 1.1.1.236, reduces tropinone to pseudotropine, diverging metabolic flux to nortropane calystegine A3. TRI activity controls metabolic flux towards hyoscyamine and downstream tropanalkaloids' biosynthesis
metabolism
two tropinone reductases (TRs) with a similar amino acid sequence constitute a branching point in TA metabolism. Both catalyze the stereospecific reduction of the 3-carbonyl group of tropinone to hydroxyl groups (tropine) with different stereospecific configurations. Tropinone reductase I (TRI, EC 1.1.1.206) reduces the ketone to the alcohol in the tropine ring to give products such as hyoscyamine and scopolamine, whereas pseudotropine reductase II (TRII) reduces tropinone to pseudotropine to give products of opposite configuration, such as the ones participating in the biosynthesis of nortropane alkaloids including calystegines. TRI and TRII compete for the same substrate tropinone. TRI plays an important role in tropane alkaloids biosynthesis
physiological function
DnTR1 regulation may be involved in a jasmonate-dependent pathway
physiological function
physiological role of tropinone reductase enzyme in tropane alkaloid biosynthesis in aerial tissues of the plant. The metabolic step of tropine formation may be regulated by, besides through the transcript and protein levels, the tissue concentration of tropinone
physiological function
tropine forming tropinone reductase (TRI) catalyzes a tropinone reduction competing with TRII, EC 1.1.1.236. Tropine formation is essential in the course of the biosynthesis of the medicinal tropine alkaloids atropine and scopolamine that are not found in potato
physiological function
in TRI-overexpressing root cultures, the hyoscyamine contents are 1.7- to 2.9fold higher than those in control
additional information
superimposition of three-dimensional models of tropinone reductases,overview
additional information
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superimposition of three-dimensional models of tropinone reductases,overview
additional information
a three dimensional model is prepared by taking Datura stramonium TR-II, PDB ID 1ipf, as template, structure comparison, overview
additional information
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a three dimensional model is prepared by taking Datura stramonium TR-II, PDB ID 1ipf, as template, structure comparison, overview
additional information
enzyme three-dimensional structure modelling
additional information
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enzyme three-dimensional structure modelling
additional information
enzyme three-dimensional structure molecular modeling, overview
additional information
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enzyme three-dimensional structure molecular modeling, overview
additional information
three-dimensional enzyme structure comparisons, overview
additional information
three-dimensional structure modelling of DnTR1, overview. DnTR1 also contains the sequence pattern G-X3-G-X-G in the cofactor binding motif and active site motif (S-N-K). The positive and negative charges on the binding pockets surface of DsTRI are due to His112. The three catalytic residues are Ser158, Tyr171, and Lys175 in DsTRI
additional information
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three-dimensional structure modelling of DnTR1, overview. DnTR1 also contains the sequence pattern G-X3-G-X-G in the cofactor binding motif and active site motif (S-N-K). The positive and negative charges on the binding pockets surface of DsTRI are due to His112. The three catalytic residues are Ser158, Tyr171, and Lys175 in DsTRI
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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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expression in Escherichia coli
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
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 TRI, sequence comparisons
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)
quantitative real-time PCR enzyme expression analysis
sixteen different peptide segment exchanges with tropinone reductase II
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TRI, DNA and amino acid sequence determiation and analysis, phylogenetic analysis and tree, quantitative real-time PCR expression level analysis, recombinant epression in Escherichia coli strain Rosetta (DE3)
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 in Escherichia coli
expression in Escherichia coli
quantitative real-time PCR enzyme expression analysis
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quantitative real-time PCR enzyme expression analysis
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Koelen, K.J.; Gross, G.G.
Partial purification and properties of tropine dehydrogenase from root cultures of Datura stramonium
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44
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Datura stramonium
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Opposite stereospecificity of two tropinone reductases is conferred by the substrate-binding sites
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Pseudomonas sp., Pseudomonas sp. AT3
-
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brenda
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Brugmansia sp., Datura stramonium
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Atropa acuminata, Atropa belladonna, Datura stramonium, Duboisia hopwoodii, Duboisia leichhardtii, Hyoscyamus albus, Hyoscyamus bohemicus, Hyoscyamus canariensis, Hyoscyamus muticus, Hyoscyamus niger, Hyoscyamus pusillus, no activity in Brassica campestris, no activity in Browallia americana, no activity in Calystegia sepium, no activity in Nicotiana tabacum, no activity in Physalis alkekengi, Physalis edulis, Physalis philadelphica, Physochlaina orientalis, Hyoscyamus niger Hn
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Nakajima, K.; Yamashita, A.; Akama, H.; Nakatsu, T.; Kato, H.; Hashimoto, T.; Oda, J.; Yamada, Y.
Crystal structures of two tropinone reductases: Different reaction stereospecificities in the same protein fold
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Datura stramonium
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162
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Hyoscyamus niger
-
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56
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Atropa belladonna, Datura stramonium (P50162)
brenda
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Tropinone reductases, enzymes at the branch point of tropane alkaloid metabolism
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67
327-337
2006
Atropa belladonna, Datura stramonium, Duboisia leichhardtii, Duboisia myoporoides, Hyoscyamus muticus, Hyoscyamus niger, Scopolia atropoides
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Brock, A.; Brandt, W.; Draeger, B.
The functional divergence of short-chain dehydrogenases involved in tropinone reduction
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54
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2008
Cochlearia officinalis (A7DY56)
brenda
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Protein structure modeling indicates hexahistidine-tag interference with enzyme activity
Proteins
72
173-183
2008
Solanum dulcamara
brenda
Kai, G.; Li, L.; Jiang, Y.; Yan, X.; Zhang, Y.; Lu, X.; Liao, P.; Chen, J.
Molecular cloning, characterization of two tropinone reductases in Anisodus acutangulus and enhancement of tropane alkaloids production in AaTRI-transformed hairy roots
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54
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Anisodus acutangulus (B2L2W8)
brenda
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Co-expression of AaPMT and AaTRI effectively enhances the yields of tropane alkaloids in Anisodus acutangulus hairy roots
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11
43
2011
Anisodus acutangulus (B2L2W8), Anisodus acutangulus
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Kushwaha, A.K.; Sangwan, N.S.; Tripathi, S.; Sangwan, R.S.
Molecular cloning and catalytic characterization of a recombinant tropine biosynthetic tropinone reductase from Withania coagulans leaf
Gene
516
238-247
2013
Withania coagulans (L7QI79), Withania coagulans
brenda
Kai, G.; Zhang, A.; Guo, Y.; Li, L.; Cui, L.; Luo, X.; Liu, C.; Xiao, J.
Enhancing the production of tropane alkaloids in transgenic Anisodus acutangulus hairy root cultures by over-expressing tropinone reductase I and hyoscyamine-6beta-hydroxylase
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Anisodus acutangulus (B2L2W8), Anisodus acutangulus
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An atypical pattern of accumulation of scopolamine and other tropane alkaloids and expression of alkaloid pathway genes in Hyoscyamus senecionis
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Hyoscyamus muticus, Hyoscyamus senecionis
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Dendrobium nobile (H9BQR7)
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Molecular cloning and characterization of a tropinone reductase from Dendrobium nobile Lindl
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Dendrobium nobile (H9BQR7), Dendrobium nobile
brenda
Qiang, W.; Xia, K.; Zhang, Q.; Zeng, J.; Huang, Y.; Yang, C.; Chen, M.; Liu, X.; Lan, X.; Liao, Z.
Functional characterisation of a tropine-forming reductase gene from Brugmansia arborea, a woody plant species producing tropane alkaloids
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127
12-22
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Brugmansia arborea (A0A088MI02), Brugmansia arborea, Datura stramonium (P50162), Datura stramonium
brenda
Kuester, N.; Rosahl, S.; Draeger, B.
Potato plants with genetically engineered tropane alkaloid precursors
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Solanum tuberosum (Q9AR59), Solanum tuberosum
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Kushwaha, A.K.; Sangwan, N.S.; Trivedi, P.K.; Negi, A.S.; Misra, L.; Sangwan, R.S.
Tropine forming tropinone reductase gene from Withania somnifera (Ashwagandha): biochemical characteristics of the recombinant enzyme and novel physiological overtones of tissue-wide gene expression patterns
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8
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Withania somnifera (U5PUZ1), Withania somnifera
brenda
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Biochemical characterization reveals the functional divergence of two tropinone reductases from Przewalskia tangutica
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Przewalskia tangutica (A0A6B7HCZ2), Przewalskia tangutica
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Zhao, K.; Zeng, J.; Zhao, T.; Zhang, H.; Qiu, F.; Yang, C.; Zeng, L.; Liu, X.; Chen, M.; Lan, X.; Liao, Z.
Enhancing tropane alkaloid production based on the functional identification of tropine-forming reductase in Scopolia lurida, a tibetan medicinal plant
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Anisodus luridus (R4QQK2)
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Qiang, W.; Xia, K.; Zhao, X.; Fu, W.; Man, J.; Zhang, M.
Cloning and enzymatic function characterization of a novel tropinone reductase I (DaTRI 2) in Datura arborea
Yao Xue Xue Bao
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Brugmansia arborea (A0A482P6A8)
-
brenda
Dehghan, E.; Reed, D.W.; Covello, P.S.; Hasanpour, Z.; Palazon, J.; Oksman-Caldentey, K.M.; Ahmadi, F.S.
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