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Information on EC 1.1.1.B51 - 3-quinuclidinone reductase (NADPH)
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The expected taxonomic range for this enzyme is: Bacteria, Eukaryota
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EC NUMBER 
COMMENTARY 
1.1.1.B51
preliminary BRENDA-supplied EC number
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RECOMMENDED NAME
GeneOntology No.
3-quinuclidinone reductase (NADPH)
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REACTION
REACTION DIAGRAM
COMMENTARY
ORGANISM
UNIPROT
LITERATURE
(R)-3-quinuclidinol + NADP+ = 3-quinuclidinone + NADPH + H+
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-
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SYSTEMATIC NAME
IUBMB Comments
(R)-3-quinuclidinol:NADP+ oxidoreductase
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ORGANISM
COMMENTARY
LITERATURE
UNIPROT
SEQUENCE DB
SOURCE
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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
3-quinuclidinone + NADPH + H+
(R)-3-quinuclidinol + NADP+
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stereospecific reduction of 3-quinuclidinone
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-
?
3-quinuclidinone + NADPH + H+
(R)-3-quinuclidinol + NADP+
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stereospecific reduction of 3-quinuclidinone with over 85-95% enantiomeric excess, effects of concentration of 3-quinuclidinone hydrochloride, overview
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-
?
3-quinuclidinone + NADPH + H+
(R)-3-quinuclidinol + NADP+
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-
-
-
?
3-quinuclidinone + NADPH + H+
(R)-3-quinuclidinol + NADP+
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-
-
?
ethyl 4-chloro-3-oxobutanoate + NADPH + H+
ethyl (S)-4-chloro-3-hydroxybutanoate + NADP+
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-
-
-
?
ethyl 4-chloro-3-oxobutanoate + NADPH + H+
ethyl (S)-4-chloro-3-hydroxybutanoate + NADP+
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-
-
?
ketopantoyl lactone + NADPH + H+
pantoyl lactone + NADP+
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the optical purity of pantoyl lactone is only 17.2% ee for L-isomer
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-
?
ketopantoyl lactone + NADPH + H+
pantoyl lactone + NADP+
the optical purity of pantoyl lactone is only 17.2% ee for L-isomer
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-
?
additional information
?
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no activity with: acetaldehyde, propionaldehyde, heptanal, glyoxal, benzaldehyde, 2-nitrobenzaldehyde, 3-nitrobenzaldehyde, 4-nitrobenzaldehyde, 2-chlorobenzaldehyde, 3-chlorobenzaldehyde, pyridine-3-aldehyde, 2,4-pentanedione, 3-methylcyclohexanone, 4-methylcyclohexanone, 4-ethylcyclohexanone, isatin, p-toluquinone, alpha-naphthoquinone, menadione, ketoisophorone, levodione, 4-piperidone hydrochloride monohydrate, 1-methyl-4-piperidone, and tropinone
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additional information
?
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no activity with: acetaldehyde, propionaldehyde, heptanal, glyoxal, benzaldehyde, 2-nitrobenzaldehyde, 3-nitrobenzaldehyde, 4-nitrobenzaldehyde, 2-chlorobenzaldehyde, 3-chlorobenzaldehyde, pyridine-3-aldehyde, 2,4-pentanedione, 3-methylcyclohexanone, 4-methylcyclohexanone, 4-ethylcyclohexanone, isatin, p-toluquinone, alpha-naphthoquinone, menadione, ketoisophorone, levodione, 4-piperidone hydrochloride monohydrate, 1-methyl-4-piperidone, and tropinone
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NATURAL SUBSTRATES
NATURAL PRODUCTS
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+
(R)-3-quinuclidinol + NADP+
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stereospecific reduction of 3-quinuclidinone
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-
?
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COFACTOR
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
NADPH
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residues R60 and S61 form hydrogen bonds with the 2'-phosphate group of the NADPH. These bonds are involved in the discrimination of NADPH from NADH
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INHIBITORS
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
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KM VALUE [mM]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
145
3-quinuclidinone
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pH 7.0, temperature not specified in the publication
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TURNOVER NUMBER [1/s]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
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SPECIFIC ACTIVITY [µmol/min/mg]
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
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pH OPTIMUM
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
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TEMPERATURE OPTIMUM
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
30
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SOURCE TISSUE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
SOURCE
additional information
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apart from D-glucose and glycerol, various sugars and alcohols like maltose, sucrose, arabinose, mannitol, sorbitol are not utilized by strain WY1202 for growth
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MOLECULAR WEIGHT
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
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SUBUNITS
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
tetramer
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Crystallization/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
sitting-drop vapor-diffusion method with a reservoir solution containing 100 mM CHES (pH 10.0), 30% PEG8000, and 3% sucrose, at 5°C
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sitting-drop vapour-diffusion method using PEG 8000 as the precipitant. The crystals belonged to space group P4(1)2(1)2, with unit-cell parameters a = b = 91.3, c = 265.4 A, and diffracted X-rays to 2.2 A resolution.The asymmetric unit contained four molecules of the protein and the solvent content was 48.4%
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Purification/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
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Cloned/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
an expression vector, pWKLQ, which contains the full length 3-quinuclidinone reductase gene is constructed. Using Escherichia coli cells coexpressing the 3-quinuclidinone reductase and glucose dehydrogenase (cofactor regeneration enzyme) genes, 618 mM 3-quinuclidinone is almost stiochiometrically converted to (R)-3-quinuclidinol with an >99.9% enantiomeric excess within 21 h of reaction
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ENGINEERING
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
I167V
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relative activity for 3-qinuclidinone is 24.5% compared to wild-type enzyme
N173A
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relative activity for 3-qinuclidinone is 97.8% compared to wild-type enzyme
Q178A
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relative activity for 3-qinuclidinone is 164.5% compared to wild-type enzyme
S168A
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relative activity for 3-qinuclidinone is 115.7% compared to wild-type enzyme
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APPLICATION
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
pharmacology
synthesis
pharmacology
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stereospecific production of (R)-3-quinuclidinol, an important chiral building block for the synthesis of various pharmaceuticals
pharmacology
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stereospecific production of (R)-3-quinuclidinol, an important chiral building block for the synthesis of various pharmaceuticals
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synthesis
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stereospecific production of (R)-3-quinuclidinol, an important chiral building block for the synthesis of various pharmaceuticals
synthesis
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the enzyme can be used for synthesis of optically pure 3-quinuclidinol. Optically pure 3-quinuclidinol is an important intermediate for the synthesis of various anticholinergic drugs. (R)-3-Quinuclidinol is used to synthesize muscarinic M1 or M3 receptor antagonists such as talsaclidine, revatropate, and solifenacin
synthesis
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stereospecific production of (R)-3-quinuclidinol, an important chiral building block for the synthesis of various pharmaceuticals
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LINKS TO OTHER DATABASES (specific for EC-Number 1.1.1.B51)
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