Any feedback?
Information on EC 1.1.1.236 - tropinone reductase II
for references in articles please use BRENDA:EC1.1.1.236Please wait a moment until all data is loaded. This message will disappear when all data is loaded.
EC Tree
1.1.1.236 tropinone reductase IIIUBMB Comments
This enzyme along with EC 1.1.1.206, tropine dehydrogenase, 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 .
Specify your search results
Word Map
- 1.1.1.236
-
tropane
- reductases
- stramonium
- datura
- scopolamine
-
calystegines
- solanaceae
- hyoscyamine
-
hyoscyamus
- tuberosum
-
solanum
- tuber
-
solanaceous
-
alkaloid-producing
- n-methylputrescine
- 3-quinuclidinone
-
enemies
-
stereoisomeric
-
herbivores
- n-methyltransferase
-
nortropane
-
nonmetal
The expected taxonomic range for this enzyme is: Eukaryota, Bacteria
Synonyms
tr-ii, tropinone reductase ii, dntr2, tropinone reductase-ii, pseudotropine-forming tropinone reductase, 
more
topPlease wait a moment until the data is sorted. This message will disappear when the data is sorted.
SYNONYM 
ORGANISM
UNIPROT
COMMENTARY 
LITERATURE
pseudotropine forming tropinone reductase
TR2
TRII
tropinone (psi-tropine-forming) reductase
-
-
-
-
tropinone reductase I
tropinone reductase II
additional information
pseudotropine forming tropinone reductase
-
-
-
-
tropinone reductase II
-
-
-
-
additional information
cf. EC 1.1.1.206, the enzyme is a member of the short-chain dehydrogenase enzyme family
additional information
-
the enzyme belongs to the family of short chain dehydrogenases
Please wait a moment until the data is sorted. This message will disappear when the data is sorted.
REACTION
REACTION DIAGRAM
COMMENTARY
ORGANISM
UNIPROT
LITERATURE
pseudotropine + NADP+ = tropinone + NADPH + H+
-
-
-
-
Please wait a moment until the data is sorted. This message will disappear when the data is sorted.
REACTION TYPE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
oxidation
-
-
-
-
redox reaction
-
-
-
-
reduction
-
-
-
-
Please wait a moment until the data is sorted. This message will disappear when the data is sorted.
PATHWAY SOURCE
PATHWAYS
Please wait a moment until the data is sorted. This message will disappear when the data is sorted.
SYSTEMATIC NAME
IUBMB Comments
pseudotropine:NADP+ 3-oxidoreductase
This enzyme along with EC 1.1.1.206, tropine dehydrogenase, represents a branch point in tropane alkaloid metabolism [3]. 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 [3]. Both enzymes are always found together in any given tropane-alkaloid-producing species, have a common substrate, tropinone, and are strictly stereospecific [2].
Please wait a moment until the data is sorted. This message will disappear when the data is sorted.
CAS REGISTRY NUMBER
COMMENTARY
136111-61-0
-
Please wait a moment until the data is sorted. This message will disappear when the data is sorted.
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
3-quinuclidinone + NADPH + H+
1-azabicyclo[2.2.2]octan-3-ol + NADP+
wild-type and mutant Y201V enzymes
-
-
r
4-methylcyclohexanone + NADPH + H+
4-methylcyclohexanol + NADP+
wild-type and mutant Y201V enzymes
-
-
r
4-methyl-cyclohexanone + NADPH
4-methylcyclohexanol + NADP+
-
-
-
-
?
4-methyl-cyclohexanone + NADPH
4-methylcyclohexanol + NADP+
-
-
-
-
?
N-methyl-4-piperidone + NADPH
N-methylpiperidin-4-ol + NADP+
-
-
-
-
?
N-methyl-4-piperidone + NADPH
N-methylpiperidin-4-ol + NADP+
-
-
-
-
?
N-methyl-4-piperidone + NADPH
N-methylpiperidin-4-ol + NADP+
-
more efficient substrate, 230% of activity with tropinone
-
-
?
N-propyl-4-piperidone + NADPH
N-propylpiperidin-4-ol + NADP+
-
-
-
-
?
N-propyl-4-piperidone + NADPH
N-propylpiperidin-4-ol + NADP+
-
more efficient substrate, 300% of activity with tropinone
-
-
?
tetrahydrothiopyran-4-one + NADPH
tetrahydrothiopyran-4-ol + NADP+
-
-
-
-
?
tetrahydrothiopyran-4-one + NADPH
tetrahydrothiopyran-4-ol + NADP+
-
-
-
-
?
tropinone + NADPH + H+
pseudotropine + NADP+
-
-
-
-
?
tropinone + NADPH + H+
pseudotropine + NADP+
reaction of tropinone reductase II, EC 1.1.1.236, tropane alkaloid biosynthesis, overview
leading to formation of calystegines
-
?
tropinone + NADPH + H+
pseudotropine + NADP+
reaction of tropinone reductase II, EC 1.1.1.236
-
-
?
tropinone + NADPH + H+
pseudotropine + NADP+
-
enzymes fails to catalyze the oxidation of tropine to tropinone in presence of NADP+
-
-
ir
tropinone + NADPH + H+
pseudotropine + NADP+
-
-
-
-
?
tropinone + NADPH + H+
pseudotropine + NADP+
-
pseudotropine oxidation never observed
-
-
ir
tropinone + NADPH + H+
pseudotropine + NADP+
one of the substrates, tropinone, is rotated relative to the en product so as to make the spatial organization in the active site favorable for the reaction to proceed
-
-
?
tropinone + NADPH + H+
pseudotropine + NADP+
recombinant enzyme mutant Y201V, no activity by wild-type TR2 enzyme
-
-
r
tropinone + NADPH + H+
pseudotropine + NADP+
-
-
-
-
?
tropinone + NADPH + H+
pseudotropine + NADP+
-
reverse reaction very inefficient, about 1.3% of the forward activity
-
-
r
tropinone + NADPH + H+
pseudotropine + NADP+
direction of biosynthesis
-
-
r
tropinone + NADPH + H+
pseudotropine + NADP+
stereospecific reduction of the 3-carbonyl group of tropinone to hydroxyl group (pseudotropine) with distinct stereospecific configuration, product identification by GC-MS analysis
-
-
r
tropinone + NADPH + H+
pseudotropine + NADP+
-
the enzyme is involved in tropane alkaloid biosynthesis, overview
leading to formation of calystegines
-
?
tropinone + NADPH + H+
pseudotropine + NADP+
-
active site structure and catalytic triad, the recombinant His-tagged enzyme shows 4fold higher activity compared to the wild-type enzyme, overview
-
-
?
tropinone + NADPH + H+
pseudotropine + NADP+
-
Solanum tuberosum tropinone reductase II reduces tropinone in vivo
-
-
r
tropinone + NADPH + H+
tropine + NADP+
-
-
only tropine formed by the reduction of tropinone, no evidence for the formation of psi-tropine
r
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 quinuclidione and 8-thiabicyclo[3.2.1]octan-2-one
-
-
?
Please wait a moment until the data is sorted. This message will disappear when the data is sorted.
NATURAL SUBSTRATE
NATURAL 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
tropinone + NADPH + H+
pseudotropine + NADP+
-
-
-
-
?
tropinone + NADPH + H+
pseudotropine + NADP+
reaction of tropinone reductase II, EC 1.1.1.236, tropane alkaloid biosynthesis, overview
leading to formation of calystegines
-
?
tropinone + NADPH + H+
pseudotropine + NADP+
-
-
-
-
?
tropinone + NADPH + H+
pseudotropine + NADP+
-
pseudotropine oxidation never observed
-
-
ir
tropinone + NADPH + H+
pseudotropine + NADP+
-
-
-
-
?
tropinone + NADPH + H+
pseudotropine + NADP+
-
reverse reaction very inefficient, about 1.3% of the forward activity
-
-
r
tropinone + NADPH + H+
pseudotropine + NADP+
direction of biosynthesis
-
-
r
tropinone + NADPH + H+
pseudotropine + NADP+
-
the enzyme is involved in tropane alkaloid biosynthesis, overview
leading to formation of calystegines
-
?
tropinone + NADPH + H+
pseudotropine + NADP+
-
Solanum tuberosum tropinone reductase II reduces tropinone in vivo
-
-
r
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
-
-
?
Please wait a moment until the data is sorted. This message will disappear when the data is sorted.
COFACTOR
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
additional information
the enzyme contains the conserved NAD(P)H binding motif (Gly-X3-Gly-X-Gly)
-
NADH
-
preference for NADPH, velocity 5.4% of the velocity found with NADPH
NADH
-
70-80% reduction in psi tropine forming reductase activity when NADH is substituted for NADPH
NADPH
the enzyme has a NADPH-binding site with a typical sequence characterized by the GXXXGXG motif
Please wait a moment until the data is sorted. This message will disappear when the data is sorted.
INHIBITOR
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
Please wait a moment until the data is sorted. This message will disappear when the data is sorted.
ACTIVATING COMPOUND
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
additional information
methyl jasmonate can enhance expression of TRII, with strong effect for TRII. TRII transcript is strongly induced, reaching the highest level after 24 h of the treatment in root and stem. TRII transcription level is highest in leaf after 12h treatment
-
Please wait a moment until the data is sorted. This message will disappear when the data is sorted.
KM VALUE [mM]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
0.016
NADPH