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Information on EC 1.1.1.236 - tropinone reductase II and Organism(s) Datura stramonium and UniProt Accession P50163

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EC Tree
IUBMB 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 .
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This record set is specific for:
Datura stramonium
UNIPROT: P50163
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The taxonomic range for the selected organisms is: Datura stramonium
The expected taxonomic range for this enzyme is: Eukaryota, Bacteria
Reaction Schemes
hide
pseudotropine
+
NADP+
=
tropinone
+
NADPH
+
H+
+
=
+
+
Synonyms
tr-ii, tropinone reductase ii, dntr2, tropinone reductase-ii, pseudotropine-forming tropinone reductase, more
SYNONYM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
tropinone reductase II
-
tropinone reductase-II
-
pseudotropine forming tropinone reductase
tropinone (psi-tropine-forming) reductase
-
-
-
-
tropinone reductase II
-
-
-
-
REACTION TYPE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
redox reaction
-
-
-
-
oxidation
-
-
-
-
reduction
-
-
-
-
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].
CAS REGISTRY NUMBER
COMMENTARY hide
136111-61-0
-
SUBSTRATE
PRODUCT                       
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate) hide
LITERATURE
(Substrate)
COMMENTARY
(Product) hide
LITERATURE
(Product)
Reversibility
r=reversible
ir=irreversible
?=not specified
psi-tropine + NADP+
tropinone + NADPH
show the reaction diagram
-
-
-
r
tropinone + NADPH + H+
pseudotropine + NADP+
show the reaction diagram
4-ethyl-cyclohexanone + NADPH
4-ethylcyclohexanol + NADP+
show the reaction diagram
-
-
-
-
?
4-methyl-cyclohexanone + NADPH
4-methylcyclohexanol + NADP+
show the reaction diagram
-
-
-
-
?
4-methyl-cyclohexanone + NADPH
? + NADP+
show the reaction diagram
-
-
-
-
?
4-tetrahydro-thiopyranone + NADP+
?
show the reaction diagram
-
-
-
-
?
6-hydroxytropinone + NADPH
? + NADP+
show the reaction diagram
-
-
-
-
?
N-(2-fluoroethyl)nortropinone + NADPH
? + NADP+
show the reaction diagram
-
-
-
-
?
N-ethylnortropinone + NADPH
? + NADP+
show the reaction diagram
-
-
-
-
?
N-iso-propylnortropinone + NADPH
? + NADP+
show the reaction diagram
-
-
-
-
?
N-methyl-4-piperidinone + NADPH
? + NADP+
show the reaction diagram
-
-
-
-
?
N-methyl-4-piperidone + NADPH
N-methylpiperidin-4-ol + NADP+
show the reaction diagram
-
-
-
-
?
N-propyl-4-piperidone + NADPH
N-propylpiperidin-4-ol + NADP+
show the reaction diagram
-
-
-
-
?
tetrahydrothiopyran-4-one + NADPH
tetrahydrothiopyran-4-ol + NADP+
show the reaction diagram
-
-
-
-
?
tropine + NADP+
tropinone + NADPH
show the reaction diagram
-
-
-
-
r
tropinone + NADPH + H+
pseudotropine + NADP+
show the reaction diagram
tropinone + NADPH + H+
tropine + NADP+
show the reaction diagram
-
-
only tropine formed by the reduction of tropinone, no evidence for the formation of psi-tropine
r
NATURAL SUBSTRATE
NATURAL PRODUCT
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate) hide
LITERATURE
(Substrate)
COMMENTARY
(Product) hide
LITERATURE
(Product)
REVERSIBILITY
r=reversible
ir=irreversible
?=not specified
tropinone + NADPH + H+
pseudotropine + NADP+
show the reaction diagram
-
-
-
?
tropinone + NADPH + H+
pseudotropine + NADP+
show the reaction diagram
COFACTOR
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
NADP+
-
oxidation does not occur when NAD+ is substituted for NADP+
NADPH
KM VALUE [mM]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.0171
NADPH
pH 7.5, 15°C
0.0949
tropinone
pH 7.5, 15°C
2.8
4-methyl-cyclohexanone
-
-
2.8
4-methylcyclohexanone
-
-
2
4-tetrahydro-thiopyranone
-
-
0.67
N-(2-fluoroethyl)nortropinone
-
-
0.25
N-ethylnortropinone
-
-
20
N-methyl-4-piperidinone
-
-
1.4
N-methylpiperid-4-one
-
-
0.00172 - 0.0255
NADPH
0.033 - 52.5
tropinone
TURNOVER NUMBER [1/s]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
71.4
NADPH
pH 7.5, 15°C
71.4
tropinone
pH 7.5, 15°C
2.73
tropinone
-
at pH 7.0
SPECIFIC ACTIVITY [µmol/min/mg]
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
additional information
-
quinuclidinone and 8-thiabicylo[3.2.1]octan-3-one are no substrates of TRII
pH OPTIMUM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
4.5 - 5
-
optimum for tetrahydrothiopyran-4-one reduction
6.8
-
tropinone reduction
9.5
-
tropine oxidation
pH RANGE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
4.5 - 8.5
-
tolerant to pH changes over a wide range
TEMPERATURE OPTIMUM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
60
-
tropine oxidation
ORGANISM
COMMENTARY hide
LITERATURE
UNIPROT
SEQUENCE DB
SOURCE
SOURCE TISSUE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
SOURCE
UNIPROT
ENTRY NAME
ORGANISM
NO. OF AA
NO. OF TRANSM. HELICES
MOLECULAR WEIGHT[Da]
SOURCE
SEQUENCE
LOCALIZATION PREDICTION?
TRN2_DATST
260
1
28311
Swiss-Prot
other Location (Reliability: 3)
MOLECULAR WEIGHT
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
25000 - 55000
-
TRII preparation is not yet pure and shows numerous bands
27700
-
3 * 27700, SDS-PAGE
28310
-
calculation from sequence of cDNA
29000
-
3 * 29000
77700
-
gel filtration
SUBUNIT
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
trimer
CRYSTALLIZATION (Commentary)
ORGANISM
UNIPROT
LITERATURE
TrII is crystallized by hanging-drop vapor diffusion with 2-methyl-2,4-pentanediol as precipitating reagent, crystals grown by macroseeding technique, crystals belong to the P4.2.2.1.2 space group with cell dimensions of a = b = 62.8 A and c = 128.4 A
-
pH STABILITY
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
4 - 8
-
keeps 90% of maximal activity in the range pH 5.2-8.2
348027
GENERAL STABILITY
ORGANISM
UNIPROT
LITERATURE
activity rapidly lost during purification
-
very unstable
-
STORAGE STABILITY
ORGANISM
UNIPROT
LITERATURE
-20°C, stable for at least 3 months
-
PURIFICATION (Commentary)
ORGANISM
UNIPROT
LITERATURE
CLONED (Commentary)
ORGANISM
UNIPROT
LITERATURE
overexpression in Atropa belladonna. Transformation with cDNA of tropinone reductases successfully alters the ratio of tropine-derived alkaloids versus pseudotropine-derived alkaloids
cDNA coding for TRI and TRII isolated and expressed in Escherichia coli NM522, P29X-encoding gene detected
-
expressed in Escherichia coli
-
TRII cDNA subcloned from pTR2EN induced in Escherichia coli BL21(DE3)
-
TRII cDNA, in Escherichia coli expression vector pET21d
-
REF.
AUTHORS
TITLE
JOURNAL
VOL.
PAGES
YEAR
ORGANISM (UNIPROT)
PUBMED ID
SOURCE
Nakajima, K.; Kato, H.; Oda, J.; Yamada, Y.; Hashimoto, T.
Site-directed mutagenesis of putative substrate-binding residues reveals a mechanism controlling the different stereospecificities of two tropinone reductases
J. Biol. Chem.
274
16563-16568
1999
Arabidopsis sp., Datura stramonium, Hyoscyamus niger
Manually annotated by BRENDA team
Boswell, H.D.; Drger, B.; McLauchlan W.R.; Portsteffen, A.; Robins D.J.; Robins R.J.; Walton, N.J.
Specificities of the enzymes of N-alkyltropane biosynthesis in Brugmansia and Datura
Phytochemistry
52
871-878
1999
Brugmansia x candida, Datura stramonium, Datura stramonium cv. D15/5, Hyoscyamus niger
Manually annotated by BRENDA team
Draeger, B.; Hashimoto, T.; Yamada, Y.
Purification and characterization of pseudotropine forming tropinone reductase from Hyoscyamus niger root cultures
Agric. Biol. Chem.
52
2663-2667
1988
Datura stramonium, Hyoscyamus niger
-
Manually annotated by BRENDA team
Couladis, M.M.; Brent Friesen, J.; Landgrebe, M.E.; Leete, E.
Enzymes catalysing the reduction of tropinone to tropine and psi-tropine isolated from the roots of Datura innoxia
Phytochemistry
30
801-805
1991
Atropa belladonna, Datura inoxia, Datura stramonium, Hyoscyamus niger
-
Manually annotated by BRENDA team
Draeger, B.; Portsteffen, A.; Schaal, A.; McCabe, P.H.; Peerless, A.C.J.; Robins, R.J.
Levels of tropinone reductase activities influence the spectrum of tropane esters found in transformed root cultures of Daura stramonium L.
Planta
188
581-586
1992
Atropa belladonna, Datura inoxia, Datura stramonium, Hyoscyamus niger, Physalis peruviana
Manually annotated by BRENDA team
Portsteffen, A.; Draeger, B.; Nahrstedt, A.
Two tropinone reducing enzymes from Datura stramonium transformed root cultures
Phytochemistry
31
1135-1138
1992
Alkekengi officinarum, Atropa belladonna, Calystegia sepium, Datura inoxia, Datura stramonium, Hyoscyamus bohemicus, Hyoscyamus canariensis, Hyoscyamus muticus, Hyoscyamus niger, Hyoscyamus pusillus, no activity in Brassica campestris, no activity in Browallia americana, no activity in Nicotiana tabacum, Physalis edulis, Physalis philadelphica, Physochlaina orientalis
-
Manually annotated by BRENDA team
Nakajima, K.; Hashimoto, T.; Yamada, Y.
Two tropinone reductases with different stereospecificities are short-chain dehydrogenases evolved from a common ancestor
Proc. Natl. Acad. Sci. USA
90
9591-9595
1993
Atropa belladonna, Datura stramonium, Hyoscyamus niger, no activity in Nicotiana tabacum
Manually annotated by BRENDA team
Portsteffen, A.; Draeger, B.; Nahrstedt, A.
The reduction of tropinone in Datura stramonium root cultures by two specific reductases
Phytochemistry
37
391-400
1994
Atropa belladonna, Datura stramonium
Manually annotated by BRENDA team
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
Proc. Natl. Acad. Sci. USA
95
4876-4881
1998
Datura stramonium, Hyoscyamus niger
Manually annotated by BRENDA team
Nakajima, K.; Hashimoto, T.
Two tropinone reductases, that catalyze opposite stereospecific reductions in tropane alkaloid biosynthesis, are localized in plant root with different cell-specific patterns
Plant Cell Physiol.
40
1099-1107
1999
Atropa belladonna, Datura stramonium, Hyoscyamus niger, no activity in Nicotiana tabacum
Manually annotated by BRENDA team
Yamashita, A.; Kato, H.; Wakatsuki, S.; Tomizaki, T.; Nakatsu, T.; Nakajima, K.; Hashimoto, T.; Yamada, Y.; Oda, J.
Structure of tropinone reductase-II complexed with NADP+ and pseudotropine at 1.9 A resolution: implication for stereospecific substrate binding and catalysis
Biochemistry
38
7630-7637
1999
Datura stramonium (P50163)
Manually annotated by BRENDA team
Keiner, R.; Kaiser, H.; Nakajima, K.; Hashimoto, T.; Draeger, B.
Molecular cloning, expression and characterization of tropinone reductase II, an enzyme of the SDR family in Solanum tuberosum (L.)
Plant Mol. Biol.
48
299-308
2002
Atropa belladonna, Datura stramonium, Hyoscyamus niger, Solanum tuberosum
Manually annotated by BRENDA team
Yamashita, A.; Endo, M.; Higashi, T.; Nakatsu, T.; Yamada, Y.; Oda, J.; Kato, H.
Capturing enzyme structure prior to reaction initiation: tropinone reductase-II-substrate complexes
Biochemistry
42
5566-5573
2003
Datura stramonium (P50163)
Manually annotated by BRENDA team
Richter, U.; Rothe, G.; Fabian, A.K.; Rahfeld, B.; Drager, B.
Overexpression of tropinone reductases alters alkaloid composition in Atropa belladonna root cultures
J. Exp. Bot.
56
645-652
2005
Datura stramonium (P50163)
Manually annotated by BRENDA team
Draeger, B.
Tropinone reductases, enzymes at the branch point of tropane alkaloid metabolism
Phytochemistry
67
327-337
2006
Atropa belladonna, Datura stramonium, Hyoscyamus niger, Solanum tuberosum
Manually annotated by BRENDA team