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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.B51
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preliminary BRENDA-supplied EC number
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.B51 3-quinuclidinone reductase (NADPH)
The expected taxonomic range for this enzyme is: Bacteria, Eukaryota
showSynonyms
RrQR, more
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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
LITERATURE
COMMENTARY
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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Substrates: stereospecific reduction of 3-quinuclidinone
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3-quinuclidinone + NADPH + H+
(R)-3-quinuclidinol + NADP+
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Substrates: 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+
Substrates: -
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3-quinuclidinone + NADPH + H+
(R)-3-quinuclidinol + NADP+
Substrates: -
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ethyl 4-chloro-3-oxobutanoate + NADPH + H+
ethyl (S)-4-chloro-3-hydroxybutanoate + NADP+
Substrates: -
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ethyl 4-chloro-3-oxobutanoate + NADPH + H+
ethyl (S)-4-chloro-3-hydroxybutanoate + NADP+
Substrates: -
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ketopantoyl lactone + NADPH + H+
pantoyl lactone + NADP+
Substrates: 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+
Substrates: the optical purity of pantoyl lactone is only 17.2% ee for L-isomer
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additional information
?
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Substrates: 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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Substrates: 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 SUBSTRATE
NATURAL PRODUCT
REACTION DIAGRAM
ORGANISM
UNIPROT
LITERATURE
COMMENTARY
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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Substrates: stereospecific reduction of 3-quinuclidinone
Products: -
Products: -
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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
Highest Expressing Human Cell Lines
Cell Line LinksPlease wait a moment until the data is sorted. This message will disappear when the data is sorted.
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
-
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
-
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
-
brenda
EXTERNAL LINKS (specific for EC-Number 1.1.1.B51)
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Release 2023.1 (January 2023)
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