BRENDA - Enzyme Database show
show all sequences of 1.1.1.B51

Stereoselective synthesis of (R)-3-quinuclidinol through asymmetric reduction of 3-quinuclidinone with 3-quinuclidinone reductase of Rhodotorula rubra

Uzura, A.; Nomoto, F.; Sakoda, A.; Nishimoto, Y.; Kataoka, M.; Shimizu, S.; Appl. Microbiol. Biotechnol. 83, 617-626 (2009)

Data extracted from this reference:

Application
Application
Commentary
Organism
pharmacology
stereospecific production of (R)-3-quinuclidinol, an important chiral building block for the synthesis of various pharmaceuticals
Rhodotorula mucilaginosa
synthesis
stereospecific production of (R)-3-quinuclidinol, an important chiral building block for the synthesis of various pharmaceuticals
Rhodotorula mucilaginosa
Cloned(Commentary)
Commentary
Organism
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
Rhodotorula mucilaginosa
Inhibitors
Inhibitors
Commentary
Organism
Structure
4-mercuribenzoate
1 mM, complete inhibition
Rhodotorula mucilaginosa
5,5'-dithiobis(2-nitrobenzoate)
1 mM, 15% inhibition
Rhodotorula mucilaginosa
Hg2+
1 mM, complete inhibition
Rhodotorula mucilaginosa
KM Value [mM]
KM Value [mM]
KM Value Maximum [mM]
Substrate
Commentary
Organism
Structure
0.19
-
NADPH
pH 7.0, temperature not specified in the publication
Rhodotorula mucilaginosa
145
-
3-quinuclidinone
pH 7.0, temperature not specified in the publication
Rhodotorula mucilaginosa
Molecular Weight [Da]
Molecular Weight [Da]
Molecular Weight Maximum [Da]
Commentary
Organism
30000
-
3 or 4 * 3 * 30000, SDS-PAGE
Rhodotorula mucilaginosa
93000
-
gel filtration
Rhodotorula mucilaginosa
Organism
Organism
Primary Accession No. (UniProt)
Commentary
Textmining
Rhodotorula mucilaginosa
B9ZZZ6
-
-
Rhodotorula mucilaginosa JCM3782
B9ZZZ6
-
-
Purification (Commentary)
Commentary
Organism
-
Rhodotorula mucilaginosa
Specific Activity [micromol/min/mg]
Specific Activity Minimum [mol/min/mg]
Specific Activity Maximum [mol/min/mg]
Commentary
Organism
341
-
pH 7.0, temperature not specified in the publication
Rhodotorula mucilaginosa
Substrates and Products (Substrate)
Substrates
Commentary Substrates
Literature (Substrates)
Organism
Products
Commentary (Products)
Literature (Products)
Organism (Products)
Reversibility
3-quinuclidinone + NADPH + H+
-
729053
Rhodotorula mucilaginosa
(R)-3-quinuclidinol + NADP+
-
-
-
?
3-quinuclidinone + NADPH + H+
-
729053
Rhodotorula mucilaginosa JCM3782
(R)-3-quinuclidinol + NADP+
-
-
-
?
ethyl 4-chloro-3-oxobutanoate + NADPH + H+
-
729053
Rhodotorula mucilaginosa
ethyl (S)-4-chloro-3-hydroxybutanoate + NADP+
-
-
-
?
ethyl 4-chloro-3-oxobutanoate + NADPH + H+
-
729053
Rhodotorula mucilaginosa JCM3782
ethyl (S)-4-chloro-3-hydroxybutanoate + NADP+
-
-
-
?
ketopantoyl lactone + NADPH + H+
the optical purity of pantoyl lactone is only 17.2% ee for L-isomer
729053
Rhodotorula mucilaginosa
pantoyl lactone + NADP+
-
-
-
?
ketopantoyl lactone + NADPH + H+
the optical purity of pantoyl lactone is only 17.2% ee for L-isomer
729053
Rhodotorula mucilaginosa JCM3782
pantoyl lactone + NADP+
-
-
-
?
additional information
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
729053
Rhodotorula mucilaginosa
?
-
-
-
-
additional information
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
729053
Rhodotorula mucilaginosa JCM3782
?
-
-
-
-
Subunits
Subunits
Commentary
Organism
?
3 or 4 * 3 * 30000, SDS-PAGE
Rhodotorula mucilaginosa
Temperature Optimum [C]
Temperature Optimum [C]
Temperature Optimum Maximum [C]
Commentary
Organism
40
-
-
Rhodotorula mucilaginosa
pH Optimum
pH Optimum Minimum
pH Optimum Maximum
Commentary
Organism
6.5
7.5
-
Rhodotorula mucilaginosa
7
-
assay at
Rhodotorula mucilaginosa
Cofactor
Cofactor
Commentary
Organism
Structure
NADPH
highly specific for NADPH as a coenzyme
Rhodotorula mucilaginosa
Application (protein specific)
Application
Commentary
Organism
pharmacology
stereospecific production of (R)-3-quinuclidinol, an important chiral building block for the synthesis of various pharmaceuticals
Rhodotorula mucilaginosa
synthesis
stereospecific production of (R)-3-quinuclidinol, an important chiral building block for the synthesis of various pharmaceuticals
Rhodotorula mucilaginosa
Cloned(Commentary) (protein specific)
Commentary
Organism
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
Rhodotorula mucilaginosa
Cofactor (protein specific)
Cofactor
Commentary
Organism
Structure
NADPH
highly specific for NADPH as a coenzyme
Rhodotorula mucilaginosa
Inhibitors (protein specific)
Inhibitors
Commentary
Organism
Structure
4-mercuribenzoate
1 mM, complete inhibition
Rhodotorula mucilaginosa
5,5'-dithiobis(2-nitrobenzoate)
1 mM, 15% inhibition
Rhodotorula mucilaginosa
Hg2+
1 mM, complete inhibition
Rhodotorula mucilaginosa
KM Value [mM] (protein specific)
KM Value [mM]
KM Value Maximum [mM]
Substrate
Commentary
Organism
Structure
0.19
-
NADPH
pH 7.0, temperature not specified in the publication
Rhodotorula mucilaginosa
145
-
3-quinuclidinone
pH 7.0, temperature not specified in the publication
Rhodotorula mucilaginosa
Molecular Weight [Da] (protein specific)
Molecular Weight [Da]
Molecular Weight Maximum [Da]
Commentary
Organism
30000
-
3 or 4 * 3 * 30000, SDS-PAGE
Rhodotorula mucilaginosa
93000
-
gel filtration
Rhodotorula mucilaginosa
Purification (Commentary) (protein specific)
Commentary
Organism
-
Rhodotorula mucilaginosa
Specific Activity [micromol/min/mg] (protein specific)
Specific Activity Minimum [mol/min/mg]
Specific Activity Maximum [mol/min/mg]
Commentary
Organism
341
-
pH 7.0, temperature not specified in the publication
Rhodotorula mucilaginosa
Substrates and Products (Substrate) (protein specific)
Substrates
Commentary Substrates
Literature (Substrates)
Organism
Products
Commentary (Products)
Literature (Products)
Organism (Products)
Reversibility
3-quinuclidinone + NADPH + H+
-
729053
Rhodotorula mucilaginosa
(R)-3-quinuclidinol + NADP+
-
-
-
?
3-quinuclidinone + NADPH + H+
-
729053
Rhodotorula mucilaginosa JCM3782
(R)-3-quinuclidinol + NADP+
-
-
-
?
ethyl 4-chloro-3-oxobutanoate + NADPH + H+
-
729053
Rhodotorula mucilaginosa
ethyl (S)-4-chloro-3-hydroxybutanoate + NADP+
-
-
-
?
ethyl 4-chloro-3-oxobutanoate + NADPH + H+
-
729053
Rhodotorula mucilaginosa JCM3782
ethyl (S)-4-chloro-3-hydroxybutanoate + NADP+
-
-
-
?
ketopantoyl lactone + NADPH + H+
the optical purity of pantoyl lactone is only 17.2% ee for L-isomer
729053
Rhodotorula mucilaginosa
pantoyl lactone + NADP+
-
-
-
?
ketopantoyl lactone + NADPH + H+
the optical purity of pantoyl lactone is only 17.2% ee for L-isomer
729053
Rhodotorula mucilaginosa JCM3782
pantoyl lactone + NADP+
-
-
-
?
additional information
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
729053
Rhodotorula mucilaginosa
?
-
-
-
-
additional information
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
729053
Rhodotorula mucilaginosa JCM3782
?
-
-
-
-
Subunits (protein specific)
Subunits
Commentary
Organism
?
3 or 4 * 3 * 30000, SDS-PAGE
Rhodotorula mucilaginosa
Temperature Optimum [C] (protein specific)
Temperature Optimum [C]
Temperature Optimum Maximum [C]
Commentary
Organism
40
-
-
Rhodotorula mucilaginosa
pH Optimum (protein specific)
pH Optimum Minimum
pH Optimum Maximum
Commentary
Organism
6.5
7.5
-
Rhodotorula mucilaginosa
7
-
assay at
Rhodotorula mucilaginosa
Other publictions for EC 1.1.1.B51
No.
1st author
Pub Med
title
organims
journal
volume
pages
year
Activating Compound
Application
Cloned(Commentary)
Crystallization (Commentary)
Engineering
General Stability
Inhibitors
KM Value [mM]
Localization
Metals/Ions
Molecular Weight [Da]
Natural Substrates/ Products (Substrates)
Organic Solvent Stability
Organism
Oxidation Stability
Posttranslational Modification
Purification (Commentary)
Reaction
Renatured (Commentary)
Source Tissue
Specific Activity [micromol/min/mg]
Storage Stability
Substrates and Products (Substrate)
Subunits
Temperature Optimum [C]
Temperature Range [C]
Temperature Stability [C]
Turnover Number [1/s]
pH Optimum
pH Range
pH Stability
Cofactor
Ki Value [mM]
pI Value
IC50 Value
Activating Compound (protein specific)
Application (protein specific)
Cloned(Commentary) (protein specific)
Cofactor (protein specific)
Crystallization (Commentary) (protein specific)
Engineering (protein specific)
General Stability (protein specific)
IC50 Value (protein specific)
Inhibitors (protein specific)
Ki Value [mM] (protein specific)
KM Value [mM] (protein specific)
Localization (protein specific)
Metals/Ions (protein specific)
Molecular Weight [Da] (protein specific)
Natural Substrates/ Products (Substrates) (protein specific)
Organic Solvent Stability (protein specific)
Oxidation Stability (protein specific)
Posttranslational Modification (protein specific)
Purification (Commentary) (protein specific)
Renatured (Commentary) (protein specific)
Source Tissue (protein specific)
Specific Activity [micromol/min/mg] (protein specific)
Storage Stability (protein specific)
Substrates and Products (Substrate) (protein specific)
Subunits (protein specific)
Temperature Optimum [C] (protein specific)
Temperature Range [C] (protein specific)
Temperature Stability [C] (protein specific)
Turnover Number [1/s] (protein specific)
pH Optimum (protein specific)
pH Range (protein specific)
pH Stability (protein specific)
pI Value (protein specific)
Expression
General Information
General Information (protein specific)
Expression (protein specific)
KCat/KM [mM/s]
KCat/KM [mM/s] (protein specific)
728943
Takeshita
Structural basis of stereospec ...
Rhodotorula mucilaginosa
AMB Express
4
0000
2014
-
-
-
1
11
-
-
5
-
-
-
-
-
1
-
-
-
-
-
-
-
-
1
1
1
-
-
5
1
-
-
1
-
-
-
-
-
-
1
1
11
-
-
-
-
5
-
-
-
-
-
-
-
-
-
-
-
-
1
1
1
-
-
5
1
-
-
-
-
-
-
-
-
-
728883
Takeshita
Crystallization and preliminar ...
Rhodotorula mucilaginosa
Acta Crystallogr. Sect. F
65
645-647
2009
-
-
1
1
-
-
-
-
-
-
-
-
-
1
-
-
1
-
-
-
-
-
-
1
-
-
-
-
-
-
-
-
-
-
-
-
-
1
-
1
-
-
-
-
-
-
-
-
-
-
-
-
-
1
-
-
-
-
-
1
-
-
-
-
-
-
-
-
-
-
-
-
-
-
729053
Uzura
Stereoselective synthesis of ( ...
Rhodotorula mucilaginosa, Rhodotorula mucilaginosa JCM3782
Appl. Microbiol. Biotechnol.
83
617-626
2009
-
2
1
-
-
-
3
2
-
-
2
-
-
2
-
-
1
-
-
-
1
-
8
1
1
-
-
-
2
-
-
1
-
-
-
-
2
1
1
-
-
-
-
3
-
2
-
-
2
-
-
-
-
1
-
-
1
-
8
1
1
-
-
-
2
-
-
-
-
-
-
-
-
-