1.1.1.206: tropinone reductase I
This is an abbreviated version!
For detailed information about tropinone reductase I, go to the full flat file.
Word Map on EC 1.1.1.206
-
1.1.1.206
-
tropane
-
reductases
-
hyoscyamine
-
scopolamine
-
datura
-
pseudotropine
-
stramonium
-
solanaceae
-
calystegines
-
putrescine
-
n-methyltransferase
-
solanaceous
-
3-quinuclidinone
-
synthesis
-
nortropane
- 1.1.1.206
-
tropane
- reductases
- hyoscyamine
- scopolamine
- datura
- pseudotropine
- stramonium
- solanaceae
-
calystegines
- putrescine
- n-methyltransferase
-
solanaceous
- 3-quinuclidinone
- synthesis
-
nortropane
Reaction
Synonyms
BaTRI, dehydrogenase, tropine, DnTR1, DsTRI, EC 1.1.1.293, More, TR-I, TR1, TRI, Tri2, tropine biosynthetic tropinone reductase, Tropine dehydrogenase, tropine-forming reductase, tropine-forming tropinone reductase, tropinone reductase, tropinone reductase I, tropinone reductase II, tropinone reductase-I, tropinone reductase-I 2, WcTR-I, WsTR-I, WsTR-I protein
ECTree
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Substrates Products
Substrates Products on EC 1.1.1.206 - tropinone reductase I
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REACTION DIAGRAM
1-propyl-4-piperidone + NADPH + H+
1-propylpiperidin-4-ol + NADP+
low activity
-
-
?
2-pyrrolidone + NADPH + H+
2-hydroxypyrrolidine + NADP+
very low activity
-
-
?
3-methyl-cyclohexanone + NADPH
3-methylcyclohexanol + NADP+
-
85% of the reaction velocity with tropinone
-
-
?
4-chloro-1-methylpiperidine + NADPH + H+
? + NADP+
moderate activity
-
-
?
4-piperidone + NADPH + H+
4-hydroxypiperidin + NADP+
very low activity
-
-
?
4-tetrahydro-thiopyranone + NADPH
?
-
83% of the reaction velocity with tropinone
-
-
?
8-thiabicyclo(3,2,1)octane-3-one + NADPH
8-thiabicyclo(3,2,1)octane-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 + H+
1-methylpiperidin-4-ol + NADP+
low activity
-
-
?
N-propyl-4-piperidinone + NADPH
N-propylpiperidinol + NADP+
-
78% of the reaction velocity with tropinone
-
-
?
3-methylcyclohexanone + NADPH
3-methylcyclohexanol + NADP+
-
-
-
-
?
3-methylcyclohexanol + NADP+
-
-
-
?
3-methylcyclohexanone + NADPH + H+
3-methylcyclohexanol + NADP+
-
-
-
?
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
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+
-
107% of the reaction velocity with tropinone
-
-
?
4-ethylcyclohexanol + NADP+
-
-
-
?
4-ethylcyclohexanone + NADPH + H+
4-ethylcyclohexanol + NADP+
low activity
-
-
?
4-methylcyclohexanone + NADPH
4-methylcyclohexanol + NADP+
-
-
-
-
?
4-methylcyclohexanone + NADPH
4-methylcyclohexanol + NADP+
-
-
-
-
?
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
-
-
?
?
-
35% of the reaction velocity with tropinone
-
-
?
8-thiabicyclo[3.2.1]octan-3-one + NADPH
?
-
40% of the reaction velocity with tropinone
-
-
?
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+
-
-
-
-
?
N-methyl-4-piperidone + NADPH
1-methylpiperidin-4-ol + NADP+
-
-
-
-
?
N-methyl-4-piperidone + NADPH
1-methylpiperidin-4-ol + NADP+
-
-
-
-
?
?
-
80% of the reaction velocity with tropinone
-
-
?
quinuclidinone + NADPH
?
-
136% of the reaction velocity with tropinone
-
-
?
tetrahydro-4H-thiopyran-4-one + NADPH + H+
? + NADP+
moderate activity
-
-
?
tropine + NADP+
tropinone + NADPH
-
last step in biosynthesis of tropine
-
-
r
tropine + NADP+
tropinone + NADPH
-
role in the pathway for tropine catabolism
-
-
r
tropine + NADP+
tropinone + NADPH
-
role in the pathway for tropine catabolism
-
-
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
pseudotropine + NADP+
-
tropinone reductase II
-
-
?
tropinone + NADPH + H+
pseudotropine + NADP+
-
tropinone reductase II
-
-
?
tropinone + NADPH + H+
tropine + NADP+
-
tropine is the precursor of the tropane alkaloids hyoscyamine and scopolamine
-
-
?
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+
-
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+
-
tropine is the precursor of the tropane alkaloids hyoscyamine and scopolamine
-
-
?
tropinone + NADPH + H+
tropine + NADP+
-
tropine is the precursor of the tropane alkaloids hyoscyamine and scopolamine
-
-
?
tropinone + NADPH + H+
tropine + NADP+
-
tropine is the precursor of the tropane alkaloids hyoscyamine and scopolamine
-
-
?
tropinone + NADPH + H+
tropine + NADP+
-
tropine is the precursor of the tropane alkaloids hyoscyamine and scopolamine
-
-
r
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
-
tropine is the precursor of the tropane alkaloids hyoscyamine and scopolamine
-
-
?
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+
Solanum tuberosum tropinone reductase I reduces tropinone in vivo
-
-
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
?
-
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 N-propyl-4-pieridinone and 4-tetrahydro-thiopyranone
-
-
?
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
-
-
?