BRENDA - Enzyme Database show
show all sequences of 1.1.1.B4

Cloning, expression, and characterization of an anti-Prelog stereospecific carbonyl reductase from Gluconobacter oxydans DSM2343

Chen, R.; Liu, X.; Wang, J.; Lin, J.; Wei, D.; Enzyme Microb. Technol. 70, 18-27 (2015)

Data extracted from this reference:

Inhibitors
Inhibitors
Commentary
Organism
Structure
Al3+
5 mM, 93% of initial activity
Gluconobacter oxydans
Fe3+
0.5 mM, 68% of initial activity
Gluconobacter oxydans
KM Value [mM]
KM Value [mM]
KM Value Maximum [mM]
Substrate
Commentary
Organism
Structure
0.18
-
NADPH
pH 7.4, 30C
Gluconobacter oxydans
0.72
-
2,3-Butanedione
pH 7.4, 30C
Gluconobacter oxydans
1.27
-
ethyl 4-chloro-3-oxobutanoate
pH 7.4, 30C
Gluconobacter oxydans
Metals/Ions
Metals/Ions
Commentary
Organism
Structure
Ca2+
5 mM, 156% of initial activity
Gluconobacter oxydans
Mg2+
5 mM, 109% of initial activity
Gluconobacter oxydans
NH4+
5 mM, 124% of initial activity
Gluconobacter oxydans
Organism
Organism
Primary Accession No. (UniProt)
Commentary
Textmining
Gluconobacter oxydans
-
-
-
Gluconobacter oxydans DSM 2343
-
-
-
Substrates and Products (Substrate)
Substrates
Commentary Substrates
Literature (Substrates)
Organism
Products
Commentary (Products)
Literature (Products)
Organism (Products)
Reversibility
1-phenyl-1,2-propandione + NADPH + H+
-
740394
Gluconobacter oxydans
? + NADP+
-
-
-
?
1-phenyl-1,2-propandione + NADPH + H+
-
740394
Gluconobacter oxydans DSM 2343
? + NADP+
-
-
-
?
2,3-butanedione + NADPH + H+
-
740394
Gluconobacter oxydans
(R)-2-hydroxy-3-oxo-butane + NADP+
-
-
-
?
2,3-butanedione + NADPH + H+
-
740394
Gluconobacter oxydans DSM 2343
(R)-2-hydroxy-3-oxo-butane + NADP+
-
-
-
?
2,3-pentanedione + NADPH + H+
-
740394
Gluconobacter oxydans
(R)-2-hydroxy-3-oxo-pentane + NADP+
-
-
-
?
2,3-pentanedione + NADPH + H+
-
740394
Gluconobacter oxydans DSM 2343
(R)-2-hydroxy-3-oxo-pentane + NADP+
-
-
-
?
4-phenylbutan-2-one + NADPH + H+
-
740394
Gluconobacter oxydans
(2R)-4-phenylbutan-2-ol + NADP+
99% conversion, 97.9% enantiomeric excess
-
-
?
ethyl 2-oxo-4-phenylbutanoate + NADPH + H+
-
740394
Gluconobacter oxydans
ethyl (2S)-2-hydroxy-4-phenylbutanoate + NADP+
93% conversion, 99% enantiomeric excess
-
-
?
ethyl 2-oxo-4-phenylbutanoate + NADPH + H+
-
740394
Gluconobacter oxydans DSM 2343
ethyl (2S)-2-hydroxy-4-phenylbutanoate + NADP+
93% conversion, 99% enantiomeric excess
-
-
?
ethyl 4-chloro-3-oxobutanoate + NADPH + H+
-
740394
Gluconobacter oxydans
ethyl (3S)-4-chloro-3-hydroxybutanoate
73.4% conversion, 99% enantiomeric excess
-
-
?
ethyl oxo(phenyl)acetate + NADPH + H+
-
740394
Gluconobacter oxydans
ethyl (2S)-hydroxy(phenyl)acetate + NADP+
-
-
-
?
additional information
the enzyme does not obey Prelog's rule and exhibits anti-Prelog enantiopreference. Hydride transfer occurs at the si faces of carbonyl group for ethyl 4-chloro-3-oxobutanoate (COBE), which is then selectively reduced to the chiral (S)-alcohol. Aromatic ketones are reduced to (R)-enantiomers, whereas keto esters are reduced to (S)-hydroxy esters with different enantioselectivities
740394
Gluconobacter oxydans
?
-
-
-
-
additional information
the enzyme does not obey Prelog's rule and exhibits anti-Prelog enantiopreference. Hydride transfer occurs at the si faces of carbonyl group for ethyl 4-chloro-3-oxobutanoate (COBE), which is then selectively reduced to the chiral (S)-alcohol. Aromatic ketones are reduced to (R)-enantiomers, whereas keto esters are reduced to (S)-hydroxy esters with different enantioselectivities
740394
Gluconobacter oxydans DSM 2343
?
-
-
-
-
Temperature Optimum [C]
Temperature Optimum [C]
Temperature Optimum Maximum [C]
Commentary
Organism
30
-
-
Gluconobacter oxydans
Turnover Number [1/s]
Turnover Number Minimum [1/s]
Turnover Number Maximum [1/s]
Substrate
Commentary
Organism
Structure
5.2
-
ethyl 4-chloro-3-oxobutanoate
pH 7.4, 30C
Gluconobacter oxydans
36.1
-
2,3-Butanedione
pH 7.4, 30C
Gluconobacter oxydans
pH Optimum
pH Optimum Minimum
pH Optimum Maximum
Commentary
Organism
9
-
-
Gluconobacter oxydans
Cofactor
Cofactor
Commentary
Organism
Structure
additional information
no cofactor: NADH
Gluconobacter oxydans
NADPH
-
Gluconobacter oxydans
Cofactor (protein specific)
Cofactor
Commentary
Organism
Structure
additional information
no cofactor: NADH
Gluconobacter oxydans
NADPH
-
Gluconobacter oxydans
Inhibitors (protein specific)
Inhibitors
Commentary
Organism
Structure
Al3+
5 mM, 93% of initial activity
Gluconobacter oxydans
Fe3+
0.5 mM, 68% of initial activity
Gluconobacter oxydans
KM Value [mM] (protein specific)
KM Value [mM]
KM Value Maximum [mM]
Substrate
Commentary
Organism
Structure
0.18
-
NADPH
pH 7.4, 30C
Gluconobacter oxydans
0.72
-
2,3-Butanedione
pH 7.4, 30C
Gluconobacter oxydans
1.27
-
ethyl 4-chloro-3-oxobutanoate
pH 7.4, 30C
Gluconobacter oxydans
Metals/Ions (protein specific)
Metals/Ions
Commentary
Organism
Structure
Ca2+
5 mM, 156% of initial activity
Gluconobacter oxydans
Mg2+
5 mM, 109% of initial activity
Gluconobacter oxydans
NH4+
5 mM, 124% of initial activity
Gluconobacter oxydans
Substrates and Products (Substrate) (protein specific)
Substrates
Commentary Substrates
Literature (Substrates)
Organism
Products
Commentary (Products)
Literature (Products)
Organism (Products)
Reversibility
1-phenyl-1,2-propandione + NADPH + H+
-
740394
Gluconobacter oxydans
? + NADP+
-
-
-
?
1-phenyl-1,2-propandione + NADPH + H+
-
740394
Gluconobacter oxydans DSM 2343
? + NADP+
-
-
-
?
2,3-butanedione + NADPH + H+
-
740394
Gluconobacter oxydans
(R)-2-hydroxy-3-oxo-butane + NADP+
-
-
-
?
2,3-butanedione + NADPH + H+
-
740394
Gluconobacter oxydans DSM 2343
(R)-2-hydroxy-3-oxo-butane + NADP+
-
-
-
?
2,3-pentanedione + NADPH + H+
-
740394
Gluconobacter oxydans
(R)-2-hydroxy-3-oxo-pentane + NADP+
-
-
-
?
2,3-pentanedione + NADPH + H+
-
740394
Gluconobacter oxydans DSM 2343
(R)-2-hydroxy-3-oxo-pentane + NADP+
-
-
-
?
4-phenylbutan-2-one + NADPH + H+
-
740394
Gluconobacter oxydans
(2R)-4-phenylbutan-2-ol + NADP+
99% conversion, 97.9% enantiomeric excess
-
-
?
ethyl 2-oxo-4-phenylbutanoate + NADPH + H+
-
740394
Gluconobacter oxydans
ethyl (2S)-2-hydroxy-4-phenylbutanoate + NADP+
93% conversion, 99% enantiomeric excess
-
-
?
ethyl 2-oxo-4-phenylbutanoate + NADPH + H+
-
740394
Gluconobacter oxydans DSM 2343
ethyl (2S)-2-hydroxy-4-phenylbutanoate + NADP+
93% conversion, 99% enantiomeric excess
-
-
?
ethyl 4-chloro-3-oxobutanoate + NADPH + H+
-
740394
Gluconobacter oxydans
ethyl (3S)-4-chloro-3-hydroxybutanoate
73.4% conversion, 99% enantiomeric excess
-
-
?
ethyl oxo(phenyl)acetate + NADPH + H+
-
740394
Gluconobacter oxydans
ethyl (2S)-hydroxy(phenyl)acetate + NADP+
-
-
-
?
additional information
the enzyme does not obey Prelog's rule and exhibits anti-Prelog enantiopreference. Hydride transfer occurs at the si faces of carbonyl group for ethyl 4-chloro-3-oxobutanoate (COBE), which is then selectively reduced to the chiral (S)-alcohol. Aromatic ketones are reduced to (R)-enantiomers, whereas keto esters are reduced to (S)-hydroxy esters with different enantioselectivities
740394
Gluconobacter oxydans
?
-
-
-
-
additional information
the enzyme does not obey Prelog's rule and exhibits anti-Prelog enantiopreference. Hydride transfer occurs at the si faces of carbonyl group for ethyl 4-chloro-3-oxobutanoate (COBE), which is then selectively reduced to the chiral (S)-alcohol. Aromatic ketones are reduced to (R)-enantiomers, whereas keto esters are reduced to (S)-hydroxy esters with different enantioselectivities
740394
Gluconobacter oxydans DSM 2343
?
-
-
-
-
Temperature Optimum [C] (protein specific)
Temperature Optimum [C]
Temperature Optimum Maximum [C]
Commentary
Organism
30
-
-
Gluconobacter oxydans
Turnover Number [1/s] (protein specific)
Turnover Number Minimum [1/s]
Turnover Number Maximum [1/s]
Substrate
Commentary
Organism
Structure
5.2
-
ethyl 4-chloro-3-oxobutanoate
pH 7.4, 30C
Gluconobacter oxydans
36.1
-
2,3-Butanedione
pH 7.4, 30C
Gluconobacter oxydans
pH Optimum (protein specific)
pH Optimum Minimum
pH Optimum Maximum
Commentary
Organism
9
-
-
Gluconobacter oxydans
KCat/KM [mM/s]
kcat/KM Value [1/mMs-1]
kcat/KM Value Maximum [1/mMs-1]
Substrate
Commentary
Organism
Structure
4.1
-
ethyl 4-chloro-3-oxobutanoate
pH 7.4, 30C
Gluconobacter oxydans
50.1
-
2,3-Butanedione
pH 7.4, 30C
Gluconobacter oxydans
KCat/KM [mM/s] (protein specific)
KCat/KM Value [1/mMs-1]
KCat/KM Value Maximum [1/mMs-1]
Substrate
Commentary
Organism
Structure
4.1
-
ethyl 4-chloro-3-oxobutanoate
pH 7.4, 30C
Gluconobacter oxydans
50.1
-
2,3-Butanedione
pH 7.4, 30C
Gluconobacter oxydans
Other publictions for EC 1.1.1.B4
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)
741784
Nealon
I86A/C295A mutant secondary a ...
Thermoanaerobacter ethanolicus
Arch. Biochem. Biophys.
606
151-156
2016
-
-
-
-
3
-
1
1
-
1
-
-
-
2
-
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1
-
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17
1
1
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-
24
1
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2
-
-
-
-
-
-
2
-
3
-
-
1
-
1
-
1
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-
-
-
-
1
-
-
-
-
17
1
1
-
-
24
1
-
-
-
-
-
-
-
26
26
742305
Peng
-
Continuous preparation of (R) ...
Morganella morganii, Morganella morganii CMCC(B)49208
Chin. J. Proc. Engin.
16
286-291
2016
-
1
-
-
-
-
-
-
-
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2
-
2
-
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4
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1
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1
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1
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1
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1
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2
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4
-
1
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-
1
-
-
-
-
-
-
-
-
-
740394
Chen
Cloning, expression, and chara ...
Gluconobacter oxydans, Gluconobacter oxydans DSM 2343
Enzyme Microb. Technol.
70
18-27
2015
-
-
-
-
-
-
2
3
-
3
-
-
-
2
-
-
-
-
-
-
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13
-
1
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2
1
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2
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2
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2
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3
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3
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-
-
13
-
1
-
-
2
1
-
-
-
-
-
-
-
2
2
739942
Wang
Cloning, expression, and direc ...
Leifsonia xyli, Leifsonia xyli HS0904
Appl. Microbiol. Biotechnol.
98
8591-8601
2014
-
1
-
-
2
-
-
6
-
-
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-
-
2
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2
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6
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1
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2
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6
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-
2
-
-
-
-
6
-
-
-
-
-
-
-
-
6
6
743703
He
-
Purification and characteriza ...
Kocuria rhizophila
Process Biochem.
49
1107-1112
2014
-
1
-
-
-
-
9
5
-
5
1
-
-
1
-
-
1
-
-
-
1
-
19
1
1
1
3
-
1
1
1
3
-
-
-
-
1
-
3
-
-
-
-
9
-
5
-
5
1
-
-
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-
1
-
-
1
-
19
1
1
1
3
-
1
1
1
-
-
-
-
-
-
-
721911
Zhou
Biocatalytic characterization ...
Carboxydothermus hydrogenoformans, Carboxydothermus hydrogenoformans DSM 6008
Biotechnol. Lett.
35
359-365
2013
-
1
1
-
-
-
-
1
-
-
1
-
4
2
-
-
-
-
-
-
-
-
15
1
1
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1
1
-
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2
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1
1
2
-
-
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1
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1
-
4
-
-
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-
-
-
-
15
1
1
-
-
1
1
-
-
-
-
-
-
-
-
-
739805
Aggarwal
Expression, purification, crys ...
Candida parapsilosis, Candida parapsilosis ATCC 7330
Acta Crystallogr. Sect. F
69
313-315
2013
-
-
1
1
-
-
-
-
-
-
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2
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2
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1
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1
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2
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-
-
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723841
Protsko
Crystallization and preliminar ...
Thermoanaerobacter ethanolicus
Acta Crystallogr. Sect. F
66
831-833
2010
-
-
1
1
1
-
-
-
-
-
1
1
-
3
-
-
1
-
-
-
-
-
1
1
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2
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1
2
1
1
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1
1
-
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-
1
-
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-
-
1
1
-
-
-
-
-
-
-
-
-
1
1
-
-
-
725726
Li
-
Deracemization of aryl seconda ...
Microbacterium oxydans, Microbacterium oxydans ECU2010
J. Mol. Catal. B
64
48-52
2010
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1
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2
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2
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4
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697267
Pal
Activity of yeast alcohol dehy ...
Saccharomyces cerevisiae, Saccharomyces pastorianus, Saccharomyces pastorianus Y379-50
Chem. Biol. Interact.
178
16-23
2009
-
-
-
-
-
-
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1
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3
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3
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1
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3
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697839
Pennacchio
Role of Tryptophan 95 in subst ...
Saccharolobus solfataricus
Extremophiles
13
751-761
2009
-
-
1
1
1
-
-
4
-
-
-
-
-
1
-
-
1
-
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-
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-
2
-
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4
-
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1
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1
1
1
1
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4
-
-
-
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1
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2
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4
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-
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-
711860
Machielsen
-
Cofactor engineering of Lactob ...
Lactobacillus brevis
Eng. Life Sci.
9
38-44
2009
-
-
1
-
5
-
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4
-
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1
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2
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2
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2
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1
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1
1
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5
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4
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2
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2
-
2
-
-
-
-
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-
4
4
684583
Pennacchio
Purification and characterizat ...
Thermus thermophilus
Appl. Environ. Microbiol.
74
3949-3958
2008
1
1
1
-
-
-
7
5
-
5
4
-
1
1
-
-
1
-
-
-
-
-
7
1
2
1
4
4
2
2
-
3
-
-
-
1
1
1
3
-
-
-
-
7
-
5
-
5
4
-
1
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1
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-
7
1
2
1
4
4
2
2
-
-
-
-
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-
-
-
688747
Nie
A novel NADH-dependent carbony ...
Candida parapsilosis
Lett. Appl. Microbiol.
44
555-562
2007
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9
-
1
1
2
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1
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1
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1
1
10
1
1
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-
1
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2
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1
2
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10
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1
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24
1
1
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1
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3
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3
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1
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3
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6
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15
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1
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1
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24
1
1
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1
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