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Information on EC 1.1.1.B51 - 3-quinuclidinone reductase (NADPH)
for references in articles please use BRENDA:EC1.1.1.B51preliminary BRENDA-supplied EC number
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1.1.1.B51 3-quinuclidinone reductase (NADPH)Specify your search results
The expected taxonomic range for this enzyme is: Bacteria, Eukaryota
Synonyms
RrQR, 
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SYNONYM 
ORGANISM
UNIPROT
COMMENTARY 
LITERATURE
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REACTION
REACTION DIAGRAM
COMMENTARY
ORGANISM
UNIPROT
LITERATURE
(R)-3-quinuclidinol + NADP+ = 3-quinuclidinone + NADPH + H+
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SYSTEMATIC NAME
IUBMB Comments
(R)-3-quinuclidinol:NADP+ oxidoreductase
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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+
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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?
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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
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
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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INHIBITOR
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
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KM VALUE [mM]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
0.19
NADPH
pH 7.0, temperature not specified in the publication
145
3-quinuclidinone
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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ORGANISM
COMMENTARY
LITERATURE
UNIPROT
SEQUENCE DB
SOURCE
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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
brenda
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UNIPROT
ENTRY NAME
ORGANISM
NO. OF AA
NO. OF TRANSM. HELICES
MOLECULAR WEIGHT[Da]
SOURCE
SEQUENCE
LOCALIZATION PREDICTION
The reliability class of the localization prediction ranges from 1 (very reliable) to 5 (not reliable).
The reliability class of the localization prediction ranges from 1 (very reliable) to 5 (not reliable). Please wait a moment until the data is sorted. This message will disappear when the data is sorted.
MOLECULAR WEIGHT
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
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SUBUNIT
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
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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PROTEIN VARIANTS
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
I167V
relative activity for 3-qinuclidinone is 24.5% compared to wild-type enzyme
N173A
relative activity for 3-qinuclidinone is 97.8% compared to wild-type enzyme
Q178A
relative activity for 3-qinuclidinone is 164.5% compared to wild-type enzyme
S168A
relative activity for 3-qinuclidinone is 115.7% compared to wild-type enzyme
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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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APPLICATION
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
pharmacology
synthesis
pharmacology
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
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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REF.
AUTHORS
TITLE
JOURNAL
VOL.
PAGES
YEAR
ORGANISM (UNIPROT)
PUBMED ID
SOURCE
Takeshita, D.; Kataoka, M.; Miyakawa, T.; Miyazono, K.; Uzura, A.; Nagata, K.; Shimizu, S.; Tanokura, M.
Crystallization and preliminary X-ray analysis of the NADPH-dependent 3-quinuclidinone reductase from Rhodotorula rubra
Acta Crystallogr. Sect. F
65
645-647
2009
Rhodotorula mucilaginosa (B9ZZZ6)
brenda
Takeshita, D.; Kataoka, M.; Miyakawa, T.; Miyazono, K.; Kumashiro, S.; Nagai, T.; Urano, N.; Uzura, A.; Nagata, K.; Shimizu, S.; Tanokura, M.
Structural basis of stereospecific reduction by quinuclidinone reductase
AMB Express
4
0000
2014
Rhodotorula mucilaginosa (B9ZZZ6)
brenda
Uzura, A.; Nomoto, F.; Sakoda, A.; Nishimoto, Y.; Kataoka, M.; Shimizu, S.
Stereoselective synthesis of (R)-3-quinuclidinol through asymmetric reduction of 3-quinuclidinone with 3-quinuclidinone reductase of Rhodotorula rubra
Appl. Microbiol. Biotechnol.
83
617-626
2009
Rhodotorula mucilaginosa (B9ZZZ6), Rhodotorula mucilaginosa JCM 3782 (B9ZZZ6)
brenda
Wang, Y.; Li, J.; Wu, Q.; Zhu, D.
Microbial stereospecific reduction of 3-quinuclidinone with newly isolated Nocardia sp. and Rhodococcus erythropolis
J. Mol. Catal. B
88
14-19
2013
Nocardia sp. WY1202
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brenda
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