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Information on EC 1.1.1.206 - tropinone reductase I
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1.1.1.206 tropinone reductase IIUBMB Comments
Also oxidizes other tropan-3alpha-ols, but not the corresponding beta-derivatives . This enzyme along with EC 1.1.1.236, tropinone reductase II, represents a branch point in tropane alkaloid metabolism . 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 . Both enzymes are always found together in any given tropane-alkaloid-producing species, have a common substrate, tropinone, and are strictly stereospecific .
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Word Map
- 1.1.1.206
-
tropane
- reductases
- hyoscyamine
- scopolamine
- datura
- pseudotropine
- stramonium
- solanaceae
-
calystegines
- putrescine
- n-methyltransferase
-
solanaceous
- 3-quinuclidinone
- synthesis
-
nortropane
The enzyme appears in viruses and cellular organisms
Synonyms
tropinone reductase, tropinone reductase i, batri, dntr1, tropine-forming reductase, tropine dehydrogenase, wstr-i, dstri, tropinone reductase-i, tropine-forming tropinone reductase, 
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SYNONYM 
ORGANISM
UNIPROT
COMMENTARY 
LITERATURE
dehydrogenase, tropine
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EC 1.1.1.293
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formerly
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TR-I
TR1
TRI
Tropine dehydrogenase
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tropine-forming reductase
tropine-forming tropinone reductase
tropinone reductase
tropinone reductase I
tropinone reductase II
additional information
tropine-forming tropinone reductase
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tropinone reductase I
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catalyses opposite stereospecific reduction to tropinone reductase II
additional information
cf. EC 1.1.1.236, the enzyme is a member of the short-chain dehydrogenase enzyme family
additional information
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the enzyme belongs to the family of short chain dehydrogenases
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REACTION
REACTION DIAGRAM
COMMENTARY
ORGANISM
UNIPROT
LITERATURE
tropine + NADP+ = tropinone + NADPH + H+
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REACTION TYPE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
oxidation
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redox reaction
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reduction
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PATHWAY SOURCE
PATHWAYS
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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].
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CAS REGISTRY NUMBER
COMMENTARY
82532-89-6
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SUBSTRATE
PRODUCT
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate)
(Substrate)
LITERATURE
(Substrate)
(Substrate)
COMMENTARY
(Product)
(Product)
LITERATURE
(Product)
(Product)
Reversibility
r=reversible
ir=irreversible
?=not specified
r=reversible
ir=irreversible
?=not specified
1-propyl-4-piperidone + NADPH + H+
1-propylpiperidin-4-ol + NADP+
low activity
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?
2-pyrrolidone + NADPH + H+
2-hydroxypyrrolidine + NADP+
very low activity
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?
3-methyl-cyclohexanone + NADPH
3-methylcyclohexanol + NADP+
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85% of the reaction velocity with tropinone
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?
4-chloro-1-methylpiperidine + NADPH + H+
? + NADP+
moderate activity
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?
4-piperidone + NADPH + H+
4-hydroxypiperidin + NADP+
very low activity
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?
4-tetrahydro-thiopyranone + NADPH
?
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83% of the reaction velocity with tropinone
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?
8-thiabicyclo(3,2,1)octane-3-one + NADPH
8-thiabicyclo(3,2,1)octane-3-ol + NADP+
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?
N-methyl-4-piperidinone + NADPH
N-methyl-1-piperidinol + NADP+
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180% of the reaction velocity with tropinone
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?
N-methyl-4-piperidinone + NADPH + H+
N-methyl-1-piperidinol + NADP+
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13% of the reaction velocity with tropinone
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?
N-methyl-4-piperidone + NADPH + H+
1-methylpiperidin-4-ol + NADP+
low activity
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?
N-propyl-4-piperidinone + NADPH
N-propylpiperidinol + NADP+
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78% of the reaction velocity with tropinone
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?
3-methylcyclohexanone + NADPH
3-methylcyclohexanol + NADP+
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?
3-methylcyclohexanone + NADPH + H+
3-methylcyclohexanol + NADP+
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?
3-methylcyclohexanone + NADPH + H+
3-methylcyclohexanol + NADP+
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?
3-quinuclidinone + NADPH + H+
1-azabicyclo[2.2.2]octan-3-ol + NADP+
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r
3-quinuclidinone + NADPH + H+
1-azabicyclo[2.2.2]octan-3-ol + NADP+
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r
3-quinuclidinone + NADPH + H+
1-azabicyclo[2.2.2]octan-3-ol + NADP+
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r
3-quinuclidinone + NADPH + H+
1-azabicyclo[2.2.2]octan-3-ol + NADP+
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r
4-ethylcyclohexanone + NADPH
4-ethylcyclohexanol + NADP+
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41% of the reaction velocity with tropinone
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?
4-ethylcyclohexanone + NADPH
4-ethylcyclohexanol + NADP+
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?
4-ethylcyclohexanone + NADPH
4-ethylcyclohexanol + NADP+
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107% of the reaction velocity with tropinone
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?
4-ethylcyclohexanone + NADPH + H+
4-ethylcyclohexanol + NADP+
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?
4-ethylcyclohexanone + NADPH + H+
4-ethylcyclohexanol + NADP+
low activity
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?
4-methylcyclohexanone + NADPH
4-methylcyclohexanol + NADP+
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?
4-methylcyclohexanone + NADPH
4-methylcyclohexanol + NADP+
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?
4-methylcyclohexanone + NADPH + H+
4-methylcyclohexanol + NADP+
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r
4-methylcyclohexanone + NADPH + H+
4-methylcyclohexanol + NADP+
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r
4-methylcyclohexanone + NADPH + H+
4-methylcyclohexanol + NADP+
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r
4-methylcyclohexanone + NADPH + H+
4-methylcyclohexanol + NADP+
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?
4-methylcyclohexanone + NADPH + H+
4-methylcyclohexanol + NADP+
low activity
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?
8-thiabicyclo[3.2.1]octan-3-one + NADPH
?
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35% of the reaction velocity with tropinone
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?
8-thiabicyclo[3.2.1]octan-3-one + NADPH
?
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40% of the reaction velocity with tropinone
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?
N-(2-fluoroethyl)nortropinone + NADPH
N-(2-fluoroethyl)nortropan-3-ol + NADP+
Brugmansia sp.
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?
N-(2-fluoroethyl)nortropinone + NADPH
N-(2-fluoroethyl)nortropan-3-ol + NADP+
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?
N-isopropylnortropinone + NADPH
N-isopropylnortropan-3-ol + NADP+
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?
N-methyl-4-piperidone + NADPH
1-methylpiperidin-4-ol + NADP+
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?
N-methyl-4-piperidone + NADPH
1-methylpiperidin-4-ol + NADP+
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?
quinuclidinone + NADPH
?
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80% of the reaction velocity with tropinone
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?
quinuclidinone + NADPH
?
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136% of the reaction velocity with tropinone
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?
tetrahydro-4H-thiopyran-4-one + NADPH + H+
? + NADP+
moderate activity
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?
tropine + NADP+
tropinone + NADPH
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last step in biosynthesis of tropine
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r
tropine + NADP+
tropinone + NADPH
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role in the pathway for tropine catabolism
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r
tropine + NADP+
tropinone + NADPH
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role in the pathway for tropine catabolism
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r
tropine + NADP+
tropinone + NADPH + H+
in vitro reaction kinetics show that the enzyme predominantly favours the reverse reaction
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r
tropine + NADP+
tropinone + NADPH + H+
catalytic kinetics of the enzyme favour the forward reaction, tropine formation
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r
tropinone + NADPH + H+
pseudotropine + NADP+
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tropinone reductase II
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?
tropinone + NADPH + H+
pseudotropine + NADP+
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tropinone reductase II
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?
tropinone + NADPH + H+
tropine + NADP+
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tropine is the precursor of the tropane alkaloids hyoscyamine and scopolamine
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?
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
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?
tropinone + NADPH + H+
tropine + NADP+
reaction of tropinone reductase I, EC 1.1.1.206
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?
tropinone + NADPH + H+
tropine + NADP+
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tropine is the precursor of the tropane alkaloids hyoscyamine and scopolamine
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r
tropinone + NADPH + H+
tropine + NADP+
tropine is the precursor of the tropane alkaloids hyoscyamine and scopolamine
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?
tropinone + NADPH + H+
tropine + NADP+
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tropine is the precursor of the tropane alkaloids hyoscyamine and scopolamine
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?
tropinone + NADPH + H+
tropine + NADP+
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tropine is the precursor of the tropane alkaloids hyoscyamine and scopolamine
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?
tropinone + NADPH + H+
tropine + NADP+
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tropine is the precursor of the tropane alkaloids hyoscyamine and scopolamine
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?
tropinone + NADPH + H+
tropine + NADP+
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tropine is the precursor of the tropane alkaloids hyoscyamine and scopolamine
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r
tropinone + NADPH + H+
tropine + NADP+
direction of biosynthesis
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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
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r
tropinone + NADPH + H+
tropine + NADP+
Scopolia atropoides
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tropine is the precursor of the tropane alkaloids hyoscyamine and scopolamine
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?
tropinone + NADPH + H+
tropine + NADP+
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the enzyme is involved in tropane alkaloid biosynthesis, e.g. of (S)-hyoscyamine, overview
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r
tropinone + NADPH + H+
tropine + NADP+
Solanum tuberosum tropinone reductase I reduces tropinone in vivo
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r
tropinone + NADPH + H+
tropine + NADP+
the reaction direction of tropinone reduction is predominantly operational in planta
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r
tropinone + NADPH + H+
tropine + NADP+
the in vitro reaction kinetics predominantly favour the reaction direction of tropinone reduction
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r
additional information
?
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significant increase of tropane alkaloids after TRI single gene transformation in Anisodus acutangulus
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?
additional information
?
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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
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?
additional information
?
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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
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?
additional information
?
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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
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?
additional information
?
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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
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?
additional information
?
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no activity with N-propyl-4-pieridinone and 4-tetrahydro-thiopyranone
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?
additional information
?
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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
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?
additional information
?
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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
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?
additional information
?
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no activity by TR-I with 1-methyl-2-pyrrolidone
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?
additional information
?
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no activity by TR-I with 1-methyl-2-pyrrolidone
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?