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EC Tree
The expected taxonomic range for this enzyme is: Bacteria, Eukaryota
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(R)-3-quinuclidinol + NADP+ = 3-quinuclidinone + NADPH + H+
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(R)-3-quinuclidinol:NADP+ oxidoreductase
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3-quinuclidinone + NADPH + H+
(R)-3-quinuclidinol + NADP+
ethyl 4-chloro-3-oxobutanoate + NADPH + H+
ethyl (S)-4-chloro-3-hydroxybutanoate + NADP+
ketopantoyl lactone + NADPH + H+
pantoyl lactone + NADP+
additional information
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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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3-quinuclidinone + NADPH + H+
(R)-3-quinuclidinol + NADP+
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stereospecific reduction of 3-quinuclidinone
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NADPH
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NADPH
highly specific for NADPH as a coenzyme
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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4-mercuribenzoate
1 mM, complete inhibition
5,5'-dithiobis(2-nitrobenzoate)
1 mM, 15% inhibition
Hg2+
1 mM, complete inhibition
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0.1 - 145
3-quinuclidinone
0.19
NADPH
pH 7.0, temperature not specified in the publication
0.1
3-quinuclidinone
pH 7.0, 30°C, mutant enzyme N173A
0.103
3-quinuclidinone
pH 7.0, 30°C, mutant enzyme Q178A
0.168
3-quinuclidinone
pH 7.0, 30°C, mutant enzyme S168A
0.308
3-quinuclidinone
pH 7.0, 30°C, mutant enzyme I167V
0.44
3-quinuclidinone
pH 7.0, 30°C, wild-type enzyme
145
3-quinuclidinone
pH 7.0, temperature not specified in the publication
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2.69 - 15.1
3-quinuclidinone
2.69
3-quinuclidinone
pH 7.0, 30°C, mutant enzyme I167V
5.62
3-quinuclidinone
pH 7.0, 30°C, mutant enzyme N173A
9.64
3-quinuclidinone
pH 7.0, 30°C, mutant enzyme S168A
9.79
3-quinuclidinone
pH 7.0, 30°C, mutant enzyme Q178A
15.1
3-quinuclidinone
pH 7.0, 30°C, wild-type enzyme
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341
pH 7.0, temperature not specified in the publication
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30
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brenda
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UniProt
brenda
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UniProt
brenda
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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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B9ZZZ6_RHOMI
272
0
29067
TrEMBL
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30000
3 or 4 * 3 * 30000, SDS-PAGE
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3 or 4 * 3 * 30000, SDS-PAGE
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3 or 4 * 3 * 30000, SDS-PAGE
tetramer
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tetramer
crystallographic data
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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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F212A
complete loss of activity
F212L
complete loss of activity
I167A
complete loss of activity
I167V
relative activity for 3-qinuclidinone is 24.5% compared to wild-type enzyme
K185A
complete loss of activity
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
S166A
complete loss of activity
S168A
relative activity for 3-qinuclidinone is 115.7% compared to wild-type enzyme
Y181A
complete loss of activity
Y181F
complete loss of activity
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Ni-affinity and ion-exchange column chromatography
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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
expressed in Escherichia coli
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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
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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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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1.1.1.B51 3-quinuclidinone reductase (NADPH)
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