1.1.1.236: tropinone reductase II
This is an abbreviated version!
For detailed information about tropinone reductase II, go to the full flat file.
Word Map on EC 1.1.1.236
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1.1.1.236
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tropane
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reductases
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stramonium
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datura
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scopolamine
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calystegines
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solanaceae
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hyoscyamine
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hyoscyamus
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tuberosum
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solanum
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tuber
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solanaceous
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alkaloid-producing
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n-methylputrescine
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3-quinuclidinone
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enemies
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stereoisomeric
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herbivores
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n-methyltransferase
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nortropane
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nonmetal
- 1.1.1.236
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tropane
- reductases
- stramonium
- datura
- scopolamine
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calystegines
- solanaceae
- hyoscyamine
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hyoscyamus
- tuberosum
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solanum
- tuber
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solanaceous
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alkaloid-producing
- n-methylputrescine
- 3-quinuclidinone
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enemies
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stereoisomeric
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herbivores
- n-methyltransferase
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nortropane
-
nonmetal
Reaction
Synonyms
DnTR2, More, pseudotropine forming tropinone reductase, pseudotropine reductase II, pseudotropine-forming tropinone reductase, pseudotropinone forming tropinone reductase, TR-II, TR2, TRII, tropinone (psi-tropine-forming) reductase, tropinone reductase, tropinone reductase I, tropinone reductase II, tropinone reductase-II
ECTree
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Substrates Products
Substrates Products on EC 1.1.1.236 - tropinone reductase II
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REACTION DIAGRAM
3-quinuclidinone + NADPH + H+
1-azabicyclo[2.2.2]octan-3-ol + NADP+
wild-type and mutant Y201V enzymes
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r
4-methylcyclohexanone + NADPH + H+
4-methylcyclohexanol + NADP+
wild-type and mutant Y201V enzymes
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r
4-methylcyclohexanol + NADP+
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-
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?
4-methyl-cyclohexanone + NADPH
4-methylcyclohexanol + NADP+
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-
-
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?
N-methylpiperidin-4-ol + NADP+
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-
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?
N-methyl-4-piperidone + NADPH
N-methylpiperidin-4-ol + NADP+
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-
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?
N-methyl-4-piperidone + NADPH
N-methylpiperidin-4-ol + NADP+
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more efficient substrate, 230% of activity with tropinone
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?
N-propylpiperidin-4-ol + NADP+
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-
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?
N-propyl-4-piperidone + NADPH
N-propylpiperidin-4-ol + NADP+
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more efficient substrate, 300% of activity with tropinone
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?
tetrahydrothiopyran-4-ol + NADP+
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?
tetrahydrothiopyran-4-one + NADPH
tetrahydrothiopyran-4-ol + NADP+
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-
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?
tropinone + NADPH + H+
pseudotropine + NADP+
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-
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?
tropinone + NADPH + H+
pseudotropine + NADP+
reaction of tropinone reductase II, EC 1.1.1.236, tropane alkaloid biosynthesis, overview
leading to formation of calystegines
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?
tropinone + NADPH + H+
pseudotropine + NADP+
reaction of tropinone reductase II, EC 1.1.1.236
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-
?
tropinone + NADPH + H+
pseudotropine + NADP+
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enzymes fails to catalyze the oxidation of tropine to tropinone in presence of NADP+
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ir
tropinone + NADPH + H+
pseudotropine + NADP+
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?
tropinone + NADPH + H+
pseudotropine + NADP+
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pseudotropine oxidation never observed
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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
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-
?
tropinone + NADPH + H+
pseudotropine + NADP+
recombinant enzyme mutant Y201V, no activity by wild-type TR2 enzyme
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-
r
tropinone + NADPH + H+
pseudotropine + NADP+
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-
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?
tropinone + NADPH + H+
pseudotropine + NADP+
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reverse reaction very inefficient, about 1.3% of the forward activity
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r
tropinone + NADPH + H+
pseudotropine + NADP+
direction of biosynthesis
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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
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r
tropinone + NADPH + H+
pseudotropine + NADP+
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the enzyme is involved in tropane alkaloid biosynthesis, overview
leading to formation of calystegines
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?
tropinone + NADPH + H+
pseudotropine + NADP+
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active site structure and catalytic triad, the recombinant His-tagged enzyme shows 4fold higher activity compared to the wild-type enzyme, overview
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?
tropinone + NADPH + H+
pseudotropine + NADP+
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Solanum tuberosum tropinone reductase II reduces tropinone in vivo
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r
tropine + NADP+
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only tropine formed by the reduction of tropinone, no evidence for the formation of psi-tropine
r
?
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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 quinuclidione and 8-thiabicyclo[3.2.1]octan-2-one
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?