BRENDA - Enzyme Database
show all sequences of 1.3.1.31

Comparison of three enoate reductases and their potential use for biotransformations

Chaparro-Riggers, J.F.; Rogers, T.A.; Vazquez-Figueroa, E.; Polizzi, K.M.; Bommarius, A.S.; Adv. Synth. Catal. 349, 1521-1531 (2007)
No PubMed abstract available

Data extracted from this reference:

Cloned(Commentary)
Cloned (Commentary)
Organism
expressed in Escherichia coli BL21(DE3)
Yersinia bercovieri
expressed in Escherichia coli BL21(DE3)
Kluyveromyces lactis
expressed in Escherichia coli BL21(DE3)
Pseudomonas putida
Inhibitors
Inhibitors
Commentary
Organism
Structure
2-cyclohexen-1-one
the addition of 260 mM 2-cyclohexen-1-one leads to a more than 30fold decrease of the half-life at 30°C
Yersinia bercovieri
additional information
not inhibited by 2-cyclohexanone
Yersinia bercovieri
KM Value [mM]
KM Value [mM]
KM Value Maximum [mM]
Substrate
Commentary
Organism
Structure
1.24
-
NADPH
at 25°C and pH 7.5
Yersinia bercovieri
Organism
Organism
UniProt
Commentary
Textmining
Kluyveromyces lactis
P40952
strain ATCC 8585D-5
-
Pseudomonas putida
Q9R9V9
xenobiotic reductase A showing enoate reductase activity
-
Yersinia bercovieri
-
strain ATCC 43970
-
Purification (Commentary)
Purification (Commentary)
Organism
Ni2+-NTA bead chromatography
Yersinia bercovieri
Ni2+-NTA bead chromatography
Kluyveromyces lactis
Ni2+-NTA bead chromatography
Pseudomonas putida
Specific Activity [micromol/min/mg]
Specific Activity Minimum [µmol/min/mg]
Specific Activity Maximum [µmol/min/mg]
Commentary
Organism
2.46
-
highest specific activity with 10 mM N-ethylmaleimide in 200 mM sodium phosphate, at pH 7.5, 0.2 mM NADPH, at 25°C
Kluyveromyces lactis
15.81
-
highest specific activity with 10 mM maleimide in 200 mM sodium phosphate, at pH 7.5, 0.2 mM NADPH, at 25°C
Yersinia bercovieri
25.82
-
highest specific activity with 10 mM maleimide in 200 mM sodium phosphate, at pH 7.5, 0.2 mM NADPH, at 25°C
Pseudomonas putida
Substrates and Products (Substrate)
Substrates
Commentary Substrates
Literature (Substrates)
Organism
Products
Commentary (Products)
Literature (Products)
Organism (Products)
Reversibility
Substrate Product ID
(R)-carvone + NADPH
-
684248
Yersinia bercovieri
2-methyl-5-(1-methylethenyl)cyclohexanone + NADP+
-
-
-
?
(R)-carvone + NADPH
-
684248
Kluyveromyces lactis
2-methyl-5-(1-methylethenyl)cyclohexanone + NADP+
-
-
-
?
(R)-carvone + NADPH
-
684248
Pseudomonas putida
2-methyl-5-(1-methylethenyl)cyclohexanone + NADP+
-
-
-
?
2-cyclohexen-1-one + NADH
-
684248
Yersinia bercovieri
2-cyclohexanone + NAD+
-
-
-
?
2-cyclohexen-1-one + NADH
-
684248
Kluyveromyces lactis
2-cyclohexanone + NAD+
-
-
-
?
2-cyclohexen-1-one + NADH
-
684248
Pseudomonas putida
2-cyclohexanone + NAD+
-
-
-
?
3-methyl-2-butenal + NADPH
-
684248
Yersinia bercovieri
3-methylbutanal + NADP+
-
-
-
?
3-methyl-2-butenal + NADPH
-
684248
Kluyveromyces lactis
3-methylbutanal + NADP+
-
-
-
?
3-methyl-2-butenal + NADPH
-
684248
Pseudomonas putida
3-methylbutanal + NADP+
-
-
-
?
but-3-en-2-one + NADPH
-
684248
Yersinia bercovieri
butan-2-one + NADP+
-
-
-
?
but-3-en-2-one + NADPH
-
684248
Kluyveromyces lactis
butan-2-one + NADP+
-
-
-
?
but-3-en-2-one + NADPH
-
684248
Pseudomonas putida
butan-2-one + NADP+
-
-
-
?
cinnamaldehyde + NADPH
-
684248
Yersinia bercovieri
?
-
-
-
?
cinnamaldehyde + NADPH
-
684248
Kluyveromyces lactis
?
-
-
-
?
cinnamaldehyde + NADPH
-
684248
Pseudomonas putida
?
-
-
-
?
citral + NADPH
-
684248
Yersinia bercovieri
3-phenylpropanal + NADP+
-
-
-
?
citral + NADPH
-
684248
Kluyveromyces lactis
3-phenylpropanal + NADP+
-
-
-
?
citral + NADPH
-
684248
Pseudomonas putida
3-phenylpropanal + NADP+
-
-
-
?
ethyl 3-(tetrahydrofuran)propanoate + NADP+
-
684248
Yersinia bercovieri
? + NADPH
-
-
-
?
ethyl 3-(tetrahydrofuran)propanoate + NADPH
-
684248
Kluyveromyces lactis
? + NADP+
-
-
-
?
ethyl 3-(tetrahydrofuran)propanoate + NADPH
-
684248
Pseudomonas putida
? + NADP+
-
-
-
?
ketoisophorone + NADPH
-
684248
Yersinia bercovieri
(6R)-levodione
-
-
-
?
ketoisophorone + NADPH
-
684248
Kluyveromyces lactis
(6R)-levodione
-
-
-
?
ketoisophorone + NADPH
-
684248
Pseudomonas putida
(6R)-levodione
-
-
-
?
maleic anhydride + NADPH
-
684248
Yersinia bercovieri
dihydrofuran-2,5-dione + NADP+
-
-
-
?
maleic anhydride + NADPH
-
684248
Kluyveromyces lactis
dihydrofuran-2,5-dione + NADP+
-
-
-
?
maleic anhydride + NADPH
-
684248
Pseudomonas putida
dihydrofuran-2,5-dione + NADP+
-
-
-
?
maleimide + NADH
-
684248
Yersinia bercovieri
pyrrolidine-2,5-dione + NADH
-
-
-
?
maleimide + NADH
-
684248
Kluyveromyces lactis
pyrrolidine-2,5-dione + NADH
-
-
-
?
maleimide + NADH
-
684248
Pseudomonas putida
pyrrolidine-2,5-dione + NADH
-
-
-
?
additional information
NADPH does not react at all in the presence of 2-cyclohexen-1-one and rarely in presence of maleimide
684248
Yersinia bercovieri
?
-
-
-
?
additional information
NADPH does not react at all in the presence of 2-cyclohexen-1-one and rarely in presence of maleimide
684248
Kluyveromyces lactis
?
-
-
-
?
additional information
NADPH does not react at all in the presence of 2-cyclohexen-1-one and rarely in presence of maleimide
684248
Pseudomonas putida
?
-
-
-
?
N-ethylmaleimide + NADPH
-
684248
Yersinia bercovieri
N-ethylpyrrolidine-2,5-dione + NADP+
-
-
-
?
N-ethylmaleimide + NADPH
-
684248
Kluyveromyces lactis
N-ethylpyrrolidine-2,5-dione + NADP+
-
-
-
?
N-ethylmaleimide + NADPH
-
684248
Pseudomonas putida
N-ethylpyrrolidine-2,5-dione + NADP+
-
-
-
?
trans,trans-2,4-hexadienal + NADPH
-
684248
Yersinia bercovieri
?
-
-
-
?
trans,trans-2,4-hexadienal + NADPH
-
684248
Kluyveromyces lactis
?
-
-
-
?
trans,trans-2,4-hexadienal + NADPH
-
684248
Pseudomonas putida
?
-
-
-
?
Synonyms
Synonyms
Commentary
Organism
enoate reductase
-
Yersinia bercovieri
enoate reductase
-
Kluyveromyces lactis
enoate reductase
-
Pseudomonas putida
KYE1
-
Kluyveromyces lactis
NADPH dehydrogenase 1
-
Kluyveromyces lactis
old yellow enzyme
-
Yersinia bercovieri
old yellow enzyme
-
Kluyveromyces lactis
old yellow enzyme
-
Pseudomonas putida
XenA
xenobiotic reductase A showing enoate reductase activity toward 2-cyclohexen-1-one
Pseudomonas putida
Yers-ER
-
Yersinia bercovieri
Temperature Stability [°C]
Temperature Stability Minimum [°C]
Temperature Stability Maximum [°C]
Commentary
Organism
30
45
KYE1 has a half-life of 1146 min at 30°C, 210 min at 37°C, and less than 5 min at 45°C
Kluyveromyces lactis
30
45
XenA has a half-life of 600 min at 30°C, 99 min at 37°C, and less than 5 min at 45°C
Pseudomonas putida
30
45
Yers-ER has a half-life of more than 2160 min at 30°C, 1488 min at 37°C, and 117 min at 45°C
Yersinia bercovieri
Turnover Number [1/s]
Turnover Number Minimum [1/s]
Turnover Number Maximum [1/s]
Substrate
Commentary
Organism
Structure
1.97
-
NADPH
at 25°C and pH 7.5
Yersinia bercovieri
pH Optimum
pH Optimum Minimum
pH Optimum Maximum
Commentary
Organism
7
-
-
Yersinia bercovieri
pH Range
pH Minimum
pH Maximum
Commentary
Organism
6
8.5
-
Yersinia bercovieri
pH Stability
pH Stability
pH Stability Maximum
Commentary
Organism
5
9.5
the activity drops off sharply between pH 5-6 and pH 8.5-9.5
Yersinia bercovieri
Cofactor
Cofactor
Commentary
Organism
Structure
NADH
the enzymes shows very little or no activity with NADH
Yersinia bercovieri
NADH
the enzymes shows very little or no activity with NADH
Kluyveromyces lactis
NADH
the enzymes shows very little or no activity with NADH
Pseudomonas putida
NADPH
preferred cofactor
Yersinia bercovieri
NADPH
preferred cofactor
Kluyveromyces lactis
NADPH
preferred cofactor
Pseudomonas putida
Cloned(Commentary) (protein specific)
Commentary
Organism
expressed in Escherichia coli BL21(DE3)
Yersinia bercovieri
expressed in Escherichia coli BL21(DE3)
Kluyveromyces lactis
expressed in Escherichia coli BL21(DE3)
Pseudomonas putida
Cofactor (protein specific)
Cofactor
Commentary
Organism
Structure
NADH
the enzymes shows very little or no activity with NADH
Yersinia bercovieri
NADH
the enzymes shows very little or no activity with NADH
Kluyveromyces lactis
NADH
the enzymes shows very little or no activity with NADH
Pseudomonas putida
NADPH
preferred cofactor
Yersinia bercovieri
NADPH
preferred cofactor
Kluyveromyces lactis
NADPH
preferred cofactor
Pseudomonas putida
Inhibitors (protein specific)
Inhibitors
Commentary
Organism
Structure
2-cyclohexen-1-one
the addition of 260 mM 2-cyclohexen-1-one leads to a more than 30fold decrease of the half-life at 30°C
Yersinia bercovieri
additional information
not inhibited by 2-cyclohexanone
Yersinia bercovieri
KM Value [mM] (protein specific)
KM Value [mM]
KM Value Maximum [mM]
Substrate
Commentary
Organism
Structure
1.24
-
NADPH
at 25°C and pH 7.5
Yersinia bercovieri
Purification (Commentary) (protein specific)
Commentary
Organism
Ni2+-NTA bead chromatography
Yersinia bercovieri
Ni2+-NTA bead chromatography
Kluyveromyces lactis
Ni2+-NTA bead chromatography
Pseudomonas putida
Specific Activity [micromol/min/mg] (protein specific)
Specific Activity Minimum [µmol/min/mg]
Specific Activity Maximum [µmol/min/mg]
Commentary
Organism
2.46
-
highest specific activity with 10 mM N-ethylmaleimide in 200 mM sodium phosphate, at pH 7.5, 0.2 mM NADPH, at 25°C
Kluyveromyces lactis
15.81
-
highest specific activity with 10 mM maleimide in 200 mM sodium phosphate, at pH 7.5, 0.2 mM NADPH, at 25°C
Yersinia bercovieri
25.82
-
highest specific activity with 10 mM maleimide in 200 mM sodium phosphate, at pH 7.5, 0.2 mM NADPH, at 25°C
Pseudomonas putida
Substrates and Products (Substrate) (protein specific)
Substrates
Commentary Substrates
Literature (Substrates)
Organism
Products
Commentary (Products)
Literature (Products)
Organism (Products)
Reversibility
ID
(R)-carvone + NADPH
-
684248
Yersinia bercovieri
2-methyl-5-(1-methylethenyl)cyclohexanone + NADP+
-
-
-
?
(R)-carvone + NADPH
-
684248
Kluyveromyces lactis
2-methyl-5-(1-methylethenyl)cyclohexanone + NADP+
-
-
-
?
(R)-carvone + NADPH
-
684248
Pseudomonas putida
2-methyl-5-(1-methylethenyl)cyclohexanone + NADP+
-
-
-
?
2-cyclohexen-1-one + NADH
-
684248
Yersinia bercovieri
2-cyclohexanone + NAD+
-
-
-
?
2-cyclohexen-1-one + NADH
-
684248
Kluyveromyces lactis
2-cyclohexanone + NAD+
-
-
-
?
2-cyclohexen-1-one + NADH
-
684248
Pseudomonas putida
2-cyclohexanone + NAD+
-
-
-
?
3-methyl-2-butenal + NADPH
-
684248
Yersinia bercovieri
3-methylbutanal + NADP+
-
-
-
?
3-methyl-2-butenal + NADPH
-
684248
Kluyveromyces lactis
3-methylbutanal + NADP+
-
-
-
?
3-methyl-2-butenal + NADPH
-
684248
Pseudomonas putida
3-methylbutanal + NADP+
-
-
-
?
but-3-en-2-one + NADPH
-
684248
Yersinia bercovieri
butan-2-one + NADP+
-
-
-
?
but-3-en-2-one + NADPH
-
684248
Kluyveromyces lactis
butan-2-one + NADP+
-
-
-
?
but-3-en-2-one + NADPH
-
684248
Pseudomonas putida
butan-2-one + NADP+
-
-
-
?
cinnamaldehyde + NADPH
-
684248
Yersinia bercovieri
?
-
-
-
?
cinnamaldehyde + NADPH
-
684248
Kluyveromyces lactis
?
-
-
-
?
cinnamaldehyde + NADPH
-
684248
Pseudomonas putida
?
-
-
-
?
citral + NADPH
-
684248
Yersinia bercovieri
3-phenylpropanal + NADP+
-
-
-
?
citral + NADPH
-
684248
Kluyveromyces lactis
3-phenylpropanal + NADP+
-
-
-
?
citral + NADPH
-
684248
Pseudomonas putida
3-phenylpropanal + NADP+
-
-
-
?
ethyl 3-(tetrahydrofuran)propanoate + NADP+
-
684248
Yersinia bercovieri
? + NADPH
-
-
-
?
ethyl 3-(tetrahydrofuran)propanoate + NADPH
-
684248
Kluyveromyces lactis
? + NADP+
-
-
-
?
ethyl 3-(tetrahydrofuran)propanoate + NADPH
-
684248
Pseudomonas putida
? + NADP+
-
-
-
?
ketoisophorone + NADPH
-
684248
Yersinia bercovieri
(6R)-levodione
-
-
-
?
ketoisophorone + NADPH
-
684248
Kluyveromyces lactis
(6R)-levodione
-
-
-
?
ketoisophorone + NADPH
-
684248
Pseudomonas putida
(6R)-levodione
-
-
-
?
maleic anhydride + NADPH
-
684248
Yersinia bercovieri
dihydrofuran-2,5-dione + NADP+
-
-
-
?
maleic anhydride + NADPH
-
684248
Kluyveromyces lactis
dihydrofuran-2,5-dione + NADP+
-
-
-
?
maleic anhydride + NADPH
-
684248
Pseudomonas putida
dihydrofuran-2,5-dione + NADP+
-
-
-
?
maleimide + NADH
-
684248
Yersinia bercovieri
pyrrolidine-2,5-dione + NADH
-
-
-
?
maleimide + NADH
-
684248
Kluyveromyces lactis
pyrrolidine-2,5-dione + NADH
-
-
-
?
maleimide + NADH
-
684248
Pseudomonas putida
pyrrolidine-2,5-dione + NADH
-
-
-
?
additional information
NADPH does not react at all in the presence of 2-cyclohexen-1-one and rarely in presence of maleimide
684248
Yersinia bercovieri
?
-
-
-
?
additional information
NADPH does not react at all in the presence of 2-cyclohexen-1-one and rarely in presence of maleimide
684248
Kluyveromyces lactis
?
-
-
-
?
additional information
NADPH does not react at all in the presence of 2-cyclohexen-1-one and rarely in presence of maleimide
684248
Pseudomonas putida
?
-
-
-
?
N-ethylmaleimide + NADPH
-
684248
Yersinia bercovieri
N-ethylpyrrolidine-2,5-dione + NADP+
-
-
-
?
N-ethylmaleimide + NADPH
-
684248
Kluyveromyces lactis
N-ethylpyrrolidine-2,5-dione + NADP+
-
-
-
?
N-ethylmaleimide + NADPH
-
684248
Pseudomonas putida
N-ethylpyrrolidine-2,5-dione + NADP+
-
-
-
?
trans,trans-2,4-hexadienal + NADPH
-
684248
Yersinia bercovieri
?
-
-
-
?
trans,trans-2,4-hexadienal + NADPH
-
684248
Kluyveromyces lactis
?
-
-
-
?
trans,trans-2,4-hexadienal + NADPH
-
684248
Pseudomonas putida
?
-
-
-
?
Temperature Stability [°C] (protein specific)
Temperature Stability Minimum [°C]
Temperature Stability Maximum [°C]
Commentary
Organism
30
45
KYE1 has a half-life of 1146 min at 30°C, 210 min at 37°C, and less than 5 min at 45°C
Kluyveromyces lactis
30
45
XenA has a half-life of 600 min at 30°C, 99 min at 37°C, and less than 5 min at 45°C
Pseudomonas putida
30
45
Yers-ER has a half-life of more than 2160 min at 30°C, 1488 min at 37°C, and 117 min at 45°C
Yersinia bercovieri
Turnover Number [1/s] (protein specific)
Turnover Number Minimum [1/s]
Turnover Number Maximum [1/s]
Substrate
Commentary
Organism
Structure
1.97
-
NADPH
at 25°C and pH 7.5
Yersinia bercovieri
pH Optimum (protein specific)
pH Optimum Minimum
pH Optimum Maximum
Commentary
Organism
7
-
-
Yersinia bercovieri
pH Range (protein specific)
pH Minimum
pH Maximum
Commentary
Organism
6
8.5
-
Yersinia bercovieri
pH Stability (protein specific)
pH Stability
pH Stability Maximum
Commentary
Organism
5
9.5
the activity drops off sharply between pH 5-6 and pH 8.5-9.5
Yersinia bercovieri
Other publictions for EC 1.3.1.31
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
Synonyms
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)
740123
Peters
Fusion proteins of an enoate r ...
Pseudomonas putida
Biol. Chem.
398
31-37
2017
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5
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4
-
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740951
Sun
Aerobic biosynthesis of hydroc ...
Clostridium acetobutylicum
Metab. Eng.
35
75-82
2016
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1
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4
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2
-
1
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1
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1
1
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2
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728964
Gall
Enzymatic conversion of flavon ...
Eubacterium ramulus
Angew. Chem. Int. Ed. Engl.
53
1439-1442
2014
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1
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2
1
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4
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2
2
2
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2
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1
2
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Clostridium tyrobutyricum
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Clostridium sporogenes, Moorella thermoacetica, Clostridium tyrobutyricum
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Thanos
Reductions of 2-enals, dehydro ...
Clostridium kluyveri, Clostridium tyrobutyricum
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4
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Thanos
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Electroenzymatic and electromi ...
Clostridium tyrobutyricum
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1
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9
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1
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4
7
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1
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Thanos
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Electro-enzymic viologen-media ...
Clostridium tyrobutyricum
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1
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3
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1
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1
1
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3
-
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-
-
-
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-
-
-
-
-
-
-
-
390675
Kuno
Structure of enoate reductase ...
Clostridium tyrobutyricum
Biol. Chem. Hoppe-Seyler
366
463-472
1985
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-
-
-
-
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4
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9
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1
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1
1
1
2
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1
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1
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4
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1
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1
1
1
2
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-
-
-
-
-
-
-
-
-
-
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-
390676
Bader
-
ATP formation is coupled to th ...
Clostridium sporogenes
FEMS Microbiol. Lett.
20
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1983
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-
-
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390677
Giesel
On the occurrence of enoate re ...
Paraclostridium bifermentans, Clostridium botulinum, Clostridioides difficile, Paeniclostridium ghonii, Tissierella praeacuta, Clostridioides mangenotii, Clostridium oceanicum, Paeniclostridium sordellii, Clostridium sporogenes, Acetoanaerobium sticklandii, no activity in Clostridium butyricum, no activity in Clostridium pasteurianum, no activity in Clostridium propionicum, Peptostreptococcus anaerobius
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390678
Giesel
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Immunological relationship of ...
Clostridium kluyveri, Clostridium sp., Clostridium sporogenes, Clostridium tyrobutyricum
FEMS Microbiol. Lett.
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1983
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4
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4
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4
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4
-
-
-
-
-
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-
-
-
-
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390679
Buehler
On the kinetics and mechanism ...
Clostridium kluyveri, Clostridium sp.
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363
609-625
1982
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31
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2
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16
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31
-
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-
-
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2
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390680
Egerer
Rhein as an electron acceptor ...
Clostridium sp.
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363
627-633
1982
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-
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1
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3
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390681
Bader
The reduction of allyl alcohol ...
Clostridium kluyveri, Clostridium sp.
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362
809-820
1981
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6
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390682
Bader
The activities of hydrogenase ...
Clostridium kluyveri, Clostridium sp.
Arch. Microbiol.
127
279-287
1980
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-
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2
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5
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4
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-
-
-
-
-
-
2
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-
2
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-
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-
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2
-
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4
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390683
Buehler
Occurrence and the possible ph ...
Clostridium kluyveri, Clostridium sp., Clostridium sporogenes, Peptostreptococcus anaerobius
FEBS Lett.
109
244-246
1980
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4
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10
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-
-
-
-
-
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4
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4
-
-
-
-
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-
-
-
-
-
-
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10
-
-
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-
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390684
Tischer
Purification and some properti ...
Clostridium kluyveri, Clostridium sp.
Eur. J. Biochem.
97
103-112
1979
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3
5
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1
2
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2
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1
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1
1
13
1
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1
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1
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3
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3
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3
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5
-
1
2
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-
1
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1
1
13
1
-
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1
-
1
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