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Information on EC 1.1.1.206 - tropinone reductase I and Organism(s) Datura stramonium and UniProt Accession P50162

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EC Tree
     1 Oxidoreductases
         1.1 Acting on the CH-OH group of donors
             1.1.1 With NAD+ or NADP+ as acceptor
                1.1.1.206 tropinone reductase I
IUBMB 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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Datura stramonium
UNIPROT: P50162
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The taxonomic range for the selected organisms is: Datura stramonium
The expected taxonomic range for this enzyme is: Bacteria, Eukaryota, Archaea
Reaction Schemes
hide
tropine
+
NADP+
=
tropinone
+
NADPH
+
H+
+
=
+
+
Synonyms
tropinone reductase, tropinone reductase i, batri, dntr1, tropine-forming reductase, tropine dehydrogenase, wstr-i, dstri, tropinone reductase-i, tropine-forming tropinone reductase, more
SYNONYM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
tropine-forming reductase
-
tropine-forming tropinone reductase
-
tropinone reductase
-
dehydrogenase, tropine
-
-
-
-
Tropine dehydrogenase
-
-
-
-
tropine-forming tropinone reductase
-
-
-
-
tropinone reductase
-
-
tropinone reductase I
-
catalyses opposite stereospecific reduction to tropinone reductase II
REACTION TYPE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
redox reaction
-
-
-
-
oxidation
-
-
-
-
reduction
-
-
-
-
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].
CAS REGISTRY NUMBER
COMMENTARY hide
82532-89-6
-
SUBSTRATE
PRODUCT                       
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate) hide
LITERATURE
(Substrate)
COMMENTARY
(Product) hide
LITERATURE
(Product)
Reversibility
r=reversible
ir=irreversible
?=not specified
3-quinuclidinone + NADPH + H+
1-azabicyclo[2.2.2]octan-3-ol + NADP+
show the reaction diagram
-
-
-
r
4-methylcyclohexanone + NADPH + H+
4-methylcyclohexanol + NADP+
show the reaction diagram
-
-
-
r
tropine + NADP+
tropinone + NADPH + H+
show the reaction diagram
-
-
-
r
tropinone + NADPH + H+
tropine + NADP+
show the reaction diagram
3-methylcyclohexanone + NADPH
3-methylcyclohexanol + NADP+
show the reaction diagram
-
-
-
-
?
3-quinuclidinone + NADPH + H+
quinuclidin-3-ol + NADP+
show the reaction diagram
-
-
-
-
?
4-ethylcyclohexanone + NADPH
4-ethylcyclohexanol + NADP+
show the reaction diagram
4-methylcyclohexanone + NADPH
4-methylcyclohexanol + NADP+
show the reaction diagram
-
-
-
-
?
4-tetrahydro-thiopyranone + NADPH
?
show the reaction diagram
-
83% of the reaction velocity with tropinone
-
-
?
7-hydroxytropinone + NADPH
7-hydroxytropan-3-ol + NADP+
show the reaction diagram
-
-
-
-
?
8-thiabicyclo[3.2.1]octan-3-one + NADPH
?
show the reaction diagram
-
35% of the reaction velocity with tropinone
-
-
?
N-(2-fluoroethyl)nortropinone + NADPH
N-(2-fluoroethyl)nortropan-3-ol + NADP+
show the reaction diagram
-
-
-
-
?
N-isopropylnortropinone + NADPH
N-isopropylnortropan-3-ol + NADP+
show the reaction diagram
-
-
-
-
?
N-methyl-4-piperidinone + NADPH
N-methyl-1-piperidinol + NADP+
show the reaction diagram
-
180% of the reaction velocity with tropinone
-
-
?
N-methyl-4-piperidone + NADPH
1-methylpiperidin-4-ol + NADP+
show the reaction diagram
-
-
-
-
?
N-propyl-4-piperidinone + NADPH
N-propylpiperidinol + NADP+
show the reaction diagram
-
78% of the reaction velocity with tropinone
-
-
?
N-propyl-4-piperidone + NADPH
1-propylpiperidin-4-ol + NADP+
show the reaction diagram
-
-
-
-
?
nortropine + NADP+
nortropinone + NADPH
show the reaction diagram
quinuclidinone + NADPH
?
show the reaction diagram
-
80% of the reaction velocity with tropinone
-
-
?
scopine + NADP+
scopinone + NADPH
show the reaction diagram
-
-
-
-
?
tropine + NADP+
tropinone + NADPH
show the reaction diagram
tropinone + NADPH + H+
tropine + NADP+
show the reaction diagram
additional information
?
-
-
no activity with 3-methyl-cyclohexanone
-
-
?
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+
tropine + NADP+
show the reaction diagram
tropine + NADP+
tropinone + NADPH
show the reaction diagram
-
last step in biosynthesis of tropine
-
-
r
tropinone + NADPH + H+
tropine + NADP+
show the reaction diagram
-
tropine is the precursor of the tropane alkaloids hyoscyamine and scopolamine
-
-
r
COFACTOR
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
NADPH
INHIBITOR
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
p-hydroxymercuribenzoate
-
14% inhibition at 0.01 mM, 56% inhibition at 0.1 mM, 100% inhibition at 1.0 mM
KM VALUE [mM]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.34
Tropine
pH 9.6, 22°C
4.18
tropinone
pH 6.4, 22°C
0.013 - 0.105
NADP+
0.023 - 0.058
NADPH
2
nortropine
-
-
3.03
Nortropinone
-
-
0.91
Scopine
-
-
0.77
Tropine
-
-
0.775 - 1.3
tropinone
additional information
additional information
-
TURNOVER NUMBER [1/s]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
3.3
Tropine
pH 9.6, 22°C
2.4
tropinone
pH 6.4, 22°C
25.6
tropinone
-
pH 7.0
kcat/KM VALUE [1/mMs-1]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
9.706
Tropine
pH 9.6, 22°C
0.574
tropinone
pH 6.4, 22°C
SPECIFIC ACTIVITY [µmol/min/mg]
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
45
-
tropinone
additional information
-
activity of 16 different mutants
pH OPTIMUM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
6.8 - 8
tropinone reduction reaction
9.9
tropine oxidation reaction
6.4
-
reduction reaction
6.8
-
tropinone reduction
9.5
-
tropine oxidation
9.9
-
oxidation reaction
TEMPERATURE OPTIMUM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
pI VALUE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
5.79
sequence calculation
ORGANISM
COMMENTARY hide
LITERATURE
UNIPROT
SEQUENCE DB
SOURCE
SOURCE TISSUE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
SOURCE
GENERAL INFORMATION
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
evolution
enzyme TRI belongs to the family of short chain dehydrogenases/reductases (SDRs) that catalyse NAD(P)(H)-dependent redox reactions
metabolism
two tropinone reductases (TRs) constitute an important branch point in the tropanalkaloid biosynthetic pathway. Tropinone reductase I or tropine-forming reductase, EC 1.1.1.206, reduces tropinone to tropine during tropanalkaloid biosynthesis, whereas tropinone reductase II, EC 1.1.1.236, reduces tropinone to pseudotropine, diverging metabolic flux to nortropane calystegine A3. TRI activity controls metabolic flux towards hyoscyamine and downstream tropanalkaloids' biosynthesis
UNIPROT
ENTRY NAME
ORGANISM
NO. OF AA
NO. OF TRANSM. HELICES
MOLECULAR WEIGHT[Da]
SOURCE
SEQUENCE
LOCALIZATION PREDICTION?
TRN1_DATST
273
1
29617
Swiss-Prot
other Location (Reliability: 2)
MOLECULAR WEIGHT
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
56000
-
gel filtration
SUBUNIT
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
dimer
-
two very similar subunits, crystallization
CRYSTALLIZATION (Commentary)
ORGANISM
UNIPROT
LITERATURE
hanging-drop vapor diffusion at 20°C
-
PROTEIN VARIANTS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
A160S
-
higher Km for tropinone that wild type enzyme
H112F
-
higher Km for tropinone that wild type enzyme
H112Y
-
higher Km for tropinone that wild type enzyme
V168E
-
lower Km for tropinone that wild type enzyme
additional information
pH STABILITY
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
6 - 10.5
-
-
347967
TEMPERATURE STABILITY
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
60
-
thermal denaturation within 10 min
70
-
thermal denaturation within 3.5 min
75
-
immediate thermal denaturation
STORAGE STABILITY
ORGANISM
UNIPROT
LITERATURE
-18°C, 50% glycerol, 3 weeks
-
4°C, 0.46 mg protein/ml, complete inactivation of enzyme activity over night
-
4°C, 2.3 mg protein/ml, 2 days, complete inactivation of enzyme activity
-
4°C, 23 mg protein/ml, 9 days, complete inactivation of enzyme activity
-
PURIFICATION (Commentary)
ORGANISM
UNIPROT
LITERATURE
wild-type and recombinant enzymes from Atropa belladonna root cultures by ammonium sulfate fractionation
CLONED (Commentary)
ORGANISM
UNIPROT
LITERATURE
gene TR1, expression in Atropa belladonna root cultures, derived from transfected leaves using the transformation system via Agrobacterium rhizogenes strain 15834
sixteen different peptide segment exchanges with tropinone reductase II
-
REF.
AUTHORS
TITLE
JOURNAL
VOL.
PAGES
YEAR
ORGANISM (UNIPROT)
PUBMED ID
SOURCE
Koelen, K.J.; Gross, G.G.
Partial purification and properties of tropine dehydrogenase from root cultures of Datura stramonium
J. Med. Plant Res.
44
227-230
1982
Datura stramonium
Manually annotated by BRENDA team
Nakajima, K.; Hashimoto, T.; Yamada, Y.
Opposite stereospecificity of two tropinone reductases is conferred by the substrate-binding sites
J. Biol. Chem.
269
11695-11698
1994
Datura stramonium
Manually annotated by BRENDA team
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
Datura stramonium
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 sp., Datura stramonium
Manually annotated by BRENDA team
Hashimoto, T.; Nakajima, K.; Ongena, G.; Yamada, Y.
Two tropinone reductases with distinct stereospecificities from cultured roots of Hyoscyamus niger
Plant Physiol.
100
836-845
1992
Atropa acuminata, Atropa belladonna, Datura stramonium, Duboisia hopwoodii, Duboisia leichhardtii, Hyoscyamus albus, Hyoscyamus bohemicus, Hyoscyamus canariensis, Hyoscyamus muticus, Hyoscyamus niger, Hyoscyamus niger Hn, Hyoscyamus pusillus, no activity in Brassica campestris, no activity in Browallia americana, no activity in Calystegia sepium, no activity in Nicotiana tabacum, no activity in Physalis alkekengi, Physalis edulis, Physalis philadelphica, Physochlaina orientalis
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
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
Atropa belladonna, Datura stramonium (P50162)
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, Duboisia leichhardtii, Duboisia myoporoides, Hyoscyamus muticus, Hyoscyamus niger, Scopolia atropoides
Manually annotated by BRENDA team
Qiang, W.; Xia, K.; Zhang, Q.; Zeng, J.; Huang, Y.; Yang, C.; Chen, M.; Liu, X.; Lan, X.; Liao, Z.
Functional characterisation of a tropine-forming reductase gene from Brugmansia arborea, a woody plant species producing tropane alkaloids
Phytochemistry
127
12-22
2016
Brugmansia arborea (A0A088MI02), Brugmansia arborea, Datura stramonium (P50162), Datura stramonium
Manually annotated by BRENDA team