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Characterization of an allylic/benzyl alcohol dehydrogenase from Yokenella sp. strain WZY002, an organism potentially useful for the synthesis of alpha,beta-unsaturated alcohols from allylic aldehydes and ketones

Ying, X.; Wang, Y.; Xiong, B.; Wu, T.; Xie, L.; Yu, M.; Wang, Z.; Appl. Environ. Microbiol. 80, 2399-2409 (2014)

Data extracted from this reference:

Activating Compound
Activating Compound
Commentary
Organism
Structure
acetone
125% activity at 20% (v/v) acetone
Yokenella sp. WZY002
dithiothreitol
123% activity at 1 mM
Yokenella sp. WZY002
EDTA
110% activity at 1 mM
Yokenella sp. WZY002
Cloned(Commentary)
Commentary
Organism
expressed in Escherichia coli BL21(DE3) cells
Yokenella sp. WZY002
Inhibitors
Inhibitors
Commentary
Organism
Structure
Ag+
complete inhibition at 1 mM
Yokenella sp. WZY002
Al3+
13.5% inhibition at 1 mM
Yokenella sp. WZY002
Co2+
80.5% inhibition at 1 mM
Yokenella sp. WZY002
Cu2+
complete inhibition at 1 mM
Yokenella sp. WZY002
Fe2+
39.7% inhibition at 1 mM
Yokenella sp. WZY002
iodoacetate
94.5% residual activity at 10 mM
Yokenella sp. WZY002
Zn2+
99.5% inhibition at 1 mM
Yokenella sp. WZY002
KM Value [mM]
KM Value [mM]
KM Value Maximum [mM]
Substrate
Commentary
Organism
Structure
0.4
-
benzaldehyde
at pH 6.5 and 65°C
Yokenella sp. WZY002
0.6
-
NADP+
with crotonaldehyde as cosubstrate, at pH 8.0 and 55°C
Yokenella sp. WZY002
0.7
-
NADP+
with crotyl alcohol as cosubstrate, at pH 8.0 and 55°C
Yokenella sp. WZY002
3.3
-
crotonaldehyde
at pH 8.0 and 55°C
Yokenella sp. WZY002
9.1
-
crotonyl alcohol
at pH 8.0 and 55°C
Yokenella sp. WZY002
14
-
benzyl alcohol
at pH 6.5 and 65°C
Yokenella sp. WZY002
Metals/Ions
Metals/Ions
Commentary
Organism
Structure
Ba2+
113% activity at 1 mM
Yokenella sp. WZY002
additional information
Ca2+, Na+, Mg2+, Mn2+, and K+ have no significant effect on the enzyme activity
Yokenella sp. WZY002
Zn2+
dependent on
Yokenella sp. WZY002
Molecular Weight [Da]
Molecular Weight [Da]
Molecular Weight Maximum [Da]
Commentary
Organism
75000
-
gel filtration
Yokenella sp. WZY002
Organic Solvent Stability
Organic Solvent
Commentary
Organism
DMSO
the enzyme retains 87.5% of the initial activity after 24 h of incubation with 20% (v/v) dimethyl sulfoxide and also remains active in 40% (v/v)
Yokenella sp. WZY002
Ethanol
the enzyme retains more than 49% of the initial activity in 20% (v/v) ethanol and also remains active in 40% (v/v)
Yokenella sp. WZY002
isopropanol
the enzyme retains more than 49% of the initial activity in 20% (v/v) isopropanol and also remains active in 40% (v/v)
Yokenella sp. WZY002
Methanol
the enzyme retains more than 49% of the initial activity in 20% (v/v) methanol and also remains active in 40% (v/v)
Yokenella sp. WZY002
Organism
Organism
Primary Accession No. (UniProt)
Commentary
Textmining
Yokenella sp. WZY002
W6CX26
-
-
Purification (Commentary)
Commentary
Organism
DEAE Sepharose column chromatography, phenyl Sepharose column chromatography, and Superdex 200 gel filtration
Yokenella sp. WZY002
Substrates and Products (Substrate)
Substrates
Commentary Substrates
Literature (Substrates)
Organism
Products
Commentary (Products)
Literature (Products)
Organism (Products)
Reversibility
(E)-oct-2-enal + NADPH + H+
-
735498
Yokenella sp. WZY002
trans-2-octen-1-ol + NADP+
-
-
-
?
1-butanol + NADP+
56% activity compared to crotyl alcohol
735498
Yokenella sp. WZY002
butyraldehyde + NADPH + H+
-
-
-
?
1-propanol + NADP+
17.4% activity compared to crotyl alcohol
735498
Yokenella sp. WZY002
propionaldehyde + NADPH + H+
-
-
-
?
2-hydroxyacetophenone + NADPH + H+
-
735498
Yokenella sp. WZY002
(S)-1,2-phenylethanediol + NADP+
-
-
-
?
acetophenone + NADPH + H+
-
735498
Yokenella sp. WZY002
?
-
-
-
r
alpha-ionone + NADPH + H+
-
735498
Yokenella sp. WZY002
?
-
-
-
r
benzaldehyde + NADPH + H+
highest reductive activity with benzaldehyde
735498
Yokenella sp. WZY002
benzyl alcohol + NADP+
-
-
-
r
benzyl alcohol + NADP+
41.7% activity compared to crotyl alcohol
735498
Yokenella sp. WZY002
benzaldehyde + NADPH + H+
-
-
-
r
crotonaldehyde + NADPH + H+
-
735498
Yokenella sp. WZY002
crotonyl alcohol + NADP+
-
-
-
r
crotonyl alcohol + NADP+
highest oxidative activity with crotyl alcohol
735498
Yokenella sp. WZY002
crotonaldehyde + NADPH + H+
-
-
-
r
additional information
no activity with NADH or NAD+
735498
Yokenella sp. WZY002
?
-
-
-
-
trans-4-phenyl-3-buten-2-one + NADPH + H+
-
735498
Yokenella sp. WZY002
?
-
-
-
r
vanillin + NADPH + H+
-
735498
Yokenella sp. WZY002
vanillic alcohol + NADP+
-
-
-
r
Subunits
Subunits
Commentary
Organism
homodimer
2 * 36411, calculated from amino acid sequence; 2 * 39000, SDS-PAGE
Yokenella sp. WZY002
Temperature Optimum [°C]
Temperature Optimum [°C]
Temperature Optimum Maximum [°C]
Commentary
Organism
55
-
for crotonyl alcohol oxidation
Yokenella sp. WZY002
65
-
for crotonaldehyde reduction
Yokenella sp. WZY002
Temperature Stability [°C]
Temperature Stability Minimum [°C]
Temperature Stability Maximum [°C]
Commentary
Organism
55
65
the enzyme shows moderate thermostability with a half-life of 6.2 h at 55°C and 1.5 h at 60°C. The activity loss at 65°C is relatively rapid, and the enzyme retains 30.8% of the initial activity after 30 min of heat treatment
Yokenella sp. WZY002
Turnover Number [1/s]
Turnover Number Minimum [1/s]
Turnover Number Maximum [1/s]
Substrate
Commentary
Organism
Structure
93.3
-
benzyl alcohol
at pH 6.5 and 65°C
Yokenella sp. WZY002
101
-
crotonyl alcohol
at pH 8.0 and 55°C
Yokenella sp. WZY002
194
-
NADP+
with crotyl alcohol as cosubstrate, at pH 8.0 and 55°C
Yokenella sp. WZY002
360
-
benzaldehyde
at pH 6.5 and 65°C
Yokenella sp. WZY002
405
-
crotonaldehyde
at pH 8.0 and 55°C
Yokenella sp. WZY002
433
-
NADP+
with crotonaldehyde as cosubstrate, at pH 8.0 and 55°C
Yokenella sp. WZY002
pH Optimum
pH Optimum Minimum
pH Optimum Maximum
Commentary
Organism
6.5
-
for crotonaldehyde reduction
Yokenella sp. WZY002
8
-
for crotonyl alcohol oxidation
Yokenella sp. WZY002
Cofactor
Cofactor
Commentary
Organism
Structure
NADP+
-
Yokenella sp. WZY002
NADPH
-
Yokenella sp. WZY002
Activating Compound (protein specific)
Activating Compound
Commentary
Organism
Structure
acetone
125% activity at 20% (v/v) acetone
Yokenella sp. WZY002
dithiothreitol
123% activity at 1 mM
Yokenella sp. WZY002
EDTA
110% activity at 1 mM
Yokenella sp. WZY002
Cloned(Commentary) (protein specific)
Commentary
Organism
expressed in Escherichia coli BL21(DE3) cells
Yokenella sp. WZY002
Cofactor (protein specific)
Cofactor
Commentary
Organism
Structure
NADP+
-
Yokenella sp. WZY002
NADPH
-
Yokenella sp. WZY002
Inhibitors (protein specific)
Inhibitors
Commentary
Organism
Structure
Ag+
complete inhibition at 1 mM
Yokenella sp. WZY002
Al3+
13.5% inhibition at 1 mM
Yokenella sp. WZY002
Co2+
80.5% inhibition at 1 mM
Yokenella sp. WZY002
Cu2+
complete inhibition at 1 mM
Yokenella sp. WZY002
Fe2+
39.7% inhibition at 1 mM
Yokenella sp. WZY002
iodoacetate
94.5% residual activity at 10 mM
Yokenella sp. WZY002
Zn2+
99.5% inhibition at 1 mM
Yokenella sp. WZY002
KM Value [mM] (protein specific)
KM Value [mM]
KM Value Maximum [mM]
Substrate
Commentary
Organism
Structure
0.4
-
benzaldehyde
at pH 6.5 and 65°C
Yokenella sp. WZY002
0.6
-
NADP+
with crotonaldehyde as cosubstrate, at pH 8.0 and 55°C
Yokenella sp. WZY002
0.7
-
NADP+
with crotyl alcohol as cosubstrate, at pH 8.0 and 55°C
Yokenella sp. WZY002
3.3
-
crotonaldehyde
at pH 8.0 and 55°C
Yokenella sp. WZY002
9.1
-
crotonyl alcohol
at pH 8.0 and 55°C
Yokenella sp. WZY002
14
-
benzyl alcohol
at pH 6.5 and 65°C
Yokenella sp. WZY002
Metals/Ions (protein specific)
Metals/Ions
Commentary
Organism
Structure
Ba2+
113% activity at 1 mM
Yokenella sp. WZY002
additional information
Ca2+, Na+, Mg2+, Mn2+, and K+ have no significant effect on the enzyme activity
Yokenella sp. WZY002
Zn2+
dependent on
Yokenella sp. WZY002
Molecular Weight [Da] (protein specific)
Molecular Weight [Da]
Molecular Weight Maximum [Da]
Commentary
Organism
75000
-
gel filtration
Yokenella sp. WZY002
Organic Solvent Stability (protein specific)
Organic Solvent
Commentary
Organism
DMSO
the enzyme retains 87.5% of the initial activity after 24 h of incubation with 20% (v/v) dimethyl sulfoxide and also remains active in 40% (v/v)
Yokenella sp. WZY002
Ethanol
the enzyme retains more than 49% of the initial activity in 20% (v/v) ethanol and also remains active in 40% (v/v)
Yokenella sp. WZY002
isopropanol
the enzyme retains more than 49% of the initial activity in 20% (v/v) isopropanol and also remains active in 40% (v/v)
Yokenella sp. WZY002
Methanol
the enzyme retains more than 49% of the initial activity in 20% (v/v) methanol and also remains active in 40% (v/v)
Yokenella sp. WZY002
Purification (Commentary) (protein specific)
Commentary
Organism
DEAE Sepharose column chromatography, phenyl Sepharose column chromatography, and Superdex 200 gel filtration
Yokenella sp. WZY002
Substrates and Products (Substrate) (protein specific)
Substrates
Commentary Substrates
Literature (Substrates)
Organism
Products
Commentary (Products)
Literature (Products)
Organism (Products)
Reversibility
(E)-oct-2-enal + NADPH + H+
-
735498
Yokenella sp. WZY002
trans-2-octen-1-ol + NADP+
-
-
-
?
1-butanol + NADP+
56% activity compared to crotyl alcohol
735498
Yokenella sp. WZY002
butyraldehyde + NADPH + H+
-
-
-
?
1-propanol + NADP+
17.4% activity compared to crotyl alcohol
735498
Yokenella sp. WZY002
propionaldehyde + NADPH + H+
-
-
-
?
2-hydroxyacetophenone + NADPH + H+
-
735498
Yokenella sp. WZY002
(S)-1,2-phenylethanediol + NADP+
-
-
-
?
acetophenone + NADPH + H+
-
735498
Yokenella sp. WZY002
?
-
-
-
r
alpha-ionone + NADPH + H+
-
735498
Yokenella sp. WZY002
?
-
-
-
r
benzaldehyde + NADPH + H+
highest reductive activity with benzaldehyde
735498
Yokenella sp. WZY002
benzyl alcohol + NADP+
-
-
-
r
benzyl alcohol + NADP+
41.7% activity compared to crotyl alcohol
735498
Yokenella sp. WZY002
benzaldehyde + NADPH + H+
-
-
-
r
crotonaldehyde + NADPH + H+
-
735498
Yokenella sp. WZY002
crotonyl alcohol + NADP+
-
-
-
r
crotonyl alcohol + NADP+
highest oxidative activity with crotyl alcohol
735498
Yokenella sp. WZY002
crotonaldehyde + NADPH + H+
-
-
-
r
additional information
no activity with NADH or NAD+
735498
Yokenella sp. WZY002
?
-
-
-
-
trans-4-phenyl-3-buten-2-one + NADPH + H+
-
735498
Yokenella sp. WZY002
?
-
-
-
r
vanillin + NADPH + H+
-
735498
Yokenella sp. WZY002
vanillic alcohol + NADP+
-
-
-
r
Subunits (protein specific)
Subunits
Commentary
Organism
homodimer
2 * 36411, calculated from amino acid sequence; 2 * 39000, SDS-PAGE
Yokenella sp. WZY002
Temperature Optimum [°C] (protein specific)
Temperature Optimum [°C]
Temperature Optimum Maximum [°C]
Commentary
Organism
55
-
for crotonyl alcohol oxidation
Yokenella sp. WZY002
65
-
for crotonaldehyde reduction
Yokenella sp. WZY002
Temperature Stability [°C] (protein specific)
Temperature Stability Minimum [°C]
Temperature Stability Maximum [°C]
Commentary
Organism
55
65
the enzyme shows moderate thermostability with a half-life of 6.2 h at 55°C and 1.5 h at 60°C. The activity loss at 65°C is relatively rapid, and the enzyme retains 30.8% of the initial activity after 30 min of heat treatment
Yokenella sp. WZY002
Turnover Number [1/s] (protein specific)
Turnover Number Minimum [1/s]
Turnover Number Maximum [1/s]
Substrate
Commentary
Organism
Structure
93.3
-
benzyl alcohol
at pH 6.5 and 65°C
Yokenella sp. WZY002
101
-
crotonyl alcohol
at pH 8.0 and 55°C
Yokenella sp. WZY002
194
-
NADP+
with crotyl alcohol as cosubstrate, at pH 8.0 and 55°C
Yokenella sp. WZY002
360
-
benzaldehyde
at pH 6.5 and 65°C
Yokenella sp. WZY002
405
-
crotonaldehyde
at pH 8.0 and 55°C
Yokenella sp. WZY002
433
-
NADP+
with crotonaldehyde as cosubstrate, at pH 8.0 and 55°C
Yokenella sp. WZY002
pH Optimum (protein specific)
pH Optimum Minimum
pH Optimum Maximum
Commentary
Organism
6.5
-
for crotonaldehyde reduction
Yokenella sp. WZY002
8
-
for crotonyl alcohol oxidation
Yokenella sp. WZY002
KCat/KM [mM/s]
kcat/KM Value [1/mMs-1]
kcat/KM Value Maximum [1/mMs-1]
Substrate
Commentary
Organism
Structure
6.6
-
benzyl alcohol
at pH 6.5 and 65°C
Yokenella sp. WZY002
11
-
crotonyl alcohol
at pH 8.0 and 55°C
Yokenella sp. WZY002
122
-
crotonaldehyde
at pH 8.0 and 55°C
Yokenella sp. WZY002
278
-
NADP+
with crotyl alcohol as cosubstrate, at pH 8.0 and 55°C
Yokenella sp. WZY002
720
-
NADP+
with crotonaldehyde as cosubstrate, at pH 8.0 and 55°C
Yokenella sp. WZY002
899
-
benzaldehyde
at pH 6.5 and 65°C
Yokenella sp. WZY002
KCat/KM [mM/s] (protein specific)
KCat/KM Value [1/mMs-1]
KCat/KM Value Maximum [1/mMs-1]
Substrate
Commentary
Organism
Structure
6.6
-
benzyl alcohol
at pH 6.5 and 65°C
Yokenella sp. WZY002
11
-
crotonyl alcohol
at pH 8.0 and 55°C
Yokenella sp. WZY002
122
-
crotonaldehyde
at pH 8.0 and 55°C
Yokenella sp. WZY002
278
-
NADP+
with crotyl alcohol as cosubstrate, at pH 8.0 and 55°C
Yokenella sp. WZY002
720
-
NADP+
with crotonaldehyde as cosubstrate, at pH 8.0 and 55°C
Yokenella sp. WZY002
899
-
benzaldehyde
at pH 6.5 and 65°C
Yokenella sp. WZY002
Other publictions for EC 1.1.1.91
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)
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Magomedova
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1
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15
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735498
Ying
Characterization of an allylic ...
Yokenella sp. WZY002
Appl. Environ. Microbiol.
80
2399-2409
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3
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7
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3
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13
1
2
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1
6
2
-
-
2
-
-
-
3
-
1
2
-
-
-
-
7
-
6
-
3
1
-
4
-
-
1
-
-
-
-
13
1
2
-
1
6
2
-
-
-
-
-
-
-
6
6
737956
Ken
-
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-
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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
-
-
8
1
-
-
1
-
1
1
-
3
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-
-
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1
3
-
-
-
-
-
-
1
-
-
-
-
-
-
-
1
-
1
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-
8
1
-
-
1
-
1
1
-
-
-
-
-
-
-
-
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-
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1
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-
12
-
-
-
-
-
2
-
-
-
-
-
-
-
-
4
-
-
-
-
12
-
-
-
-
-
-
-
-
-
-
-
1
3
-
-
-
-
12
-
-
-
-
-
-
-
-
-
-
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-
4
-
-
-
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12
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8
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-
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1
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-
1
-
-
1
-
-
-
-
-
27
-
1
-
-
14
2
-
-
-
8
-
-
-
-
1
-
-
-
-
-
8
8
14
-
-
1
-
-
-
-
1
-
-
-
-
27
-
1
-
-
14
2
-
-
-
-
-
-
-
14
14
389607
Gutierrez
Anisaldehyde production and ar ...
Pleurotus pulmonarius
Appl. Environ. Microbiol.
60
1783-1788
1994
-
-
-
-
-
-
-
-
-
-
-
-
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1
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1
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1
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-
1
-
-
1
-
-
-
-
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-
-
-
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-
389606
Muheim
Purification and properties of ...
Phanerochaete chrysosporium
Eur. J. Biochem.
195
369-375
1991
-
-
-
-
-
-
5
-
-
-
2
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-
1
-
-
1
-
-
-
-
2
11
1
-
-
-
-
1
1
-
1
-
-
-
-
-
-
1
-
-
-
-
5
-
-
-
-
2
-
-
-
-
1
-
-
-
2
11
1
-
-
-
-
1
1
-
-
-
-
-
-
-
-
288179
Kato
-
Reductive transformation of be ...
Nocardia asteroides, Nocardia asteroides JCM3016
J. Ferment. Bioeng.
69
220-223
1990
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-
-
-
-
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1
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3
-
2
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1
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3
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1
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-
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1
-
3
-
-
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-
-
-
1
-
3
-
1
-
-
-
-
-
-
-
-
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-
-
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-
389479
Dalkin
Stress responses in alfalfa (M ...
Medicago sativa
Plant Physiol.
92
440-446
1990
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-
-
-
-
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-
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1
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1
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-
1
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-
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-
-
-
-
-
-
-
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-
-
-
-
389592
Jaaska
-
Isoenzymes of aromatic alcohol ...
Dasypyrum villosum, Elymus repens, Secale cereale, Secale montanum, Secale sylvestre, Triticale turgidocereale, Triticum monococcum subsp. aegilopoides, Triticum turgidum
Biochem. Physiol. Pflanz.
179
21-30
1984
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-
-
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-
-
16
-
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-
8
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8
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-
1
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16
-
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8
-
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-
1
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-
389602
Rhodes
-
Changes in the activity of enz ...
Solanum lycopersicum
Phytochemistry
16
655-659
1977
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-
-
-
-
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1
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1
1
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1
1
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-
389603
Mansell
-
Multiple forms and specificity ...
Picea abies
Phytochemistry
15
1849-1853
1976
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1
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1
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1
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2
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2
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1
-
1
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-
389601
Rhodes
-
Enzymes involved in the reduct ...
Brassica napus subsp. rapifera
Phytochemistry
14
1235-1240
1975
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-
-
-
-
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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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2
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2
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4
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1
-
1
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-
1
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-
389598
Davies
-
Aromatic alcohol dehydrogenase ...
Solanum tuberosum
Phytochemistry
12
531-536
1973
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-
-
-
-
-
-
21
-
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1
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1
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1
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1
15
-
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2
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2
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-
21
-
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-
1
-
1
-
1
15
-
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-
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-
389605
Sloane
Metabolites of p-aminobenzoic ...
Mycobacterium tuberculosis
Biochim. Biophys. Acta
327
11-19
1973
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-
-
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2
2
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1
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1
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2
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1
3
-
3
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3
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2
-
2
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1
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2
-
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-
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-
1
3
-
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-
389599
Gross
Reduction of aromatic acids to ...
Neurospora crassa
Eur. J. Biochem.
8
420-425
1969
-
-
-
-
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-
2
5
-
-
1
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1
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1
-
-
1
1
1
11
-
1
1
-
-
2
-
-
2
-
-
-
-
-
-
2
-
-
-
-
2
-
5
-
-
1
-
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-
-
1
-
1
1
1
11
-
1
1
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-
2
-
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-