Information on EC 1.1.1.B3 - (S)-specific secondary alcohol dehydrogenase

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The expected taxonomic range for this enzyme is: Eukaryota, Bacteria, Archaea

EC NUMBER
COMMENTARY hide
1.1.1.B3
preliminary BRENDA-supplied EC number
RECOMMENDED NAME
GeneOntology No.
(S)-specific secondary alcohol dehydrogenase
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REACTION
REACTION DIAGRAM
COMMENTARY hide
ORGANISM
UNIPROT
LITERATURE
(S)-R-CHOH-R' + NAD+ = R-CO-R' + NADH + H+
show the reaction diagram
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-
-
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PATHWAY
BRENDA Link
KEGG Link
MetaCyc Link
non-pathway related
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SYSTEMATIC NAME
IUBMB Comments
sec-alcohol:NAD+ oxidoreductase (specific for (S)-configuration of alcohol)
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ORGANISM
COMMENTARY hide
LITERATURE
UNIPROT
SEQUENCE DB
SOURCE
strain MTCC 5158
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Manually annotated by BRENDA team
strain MTCC 5158
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Manually annotated by BRENDA team
Nocardia fusca AKU 2123
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-
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Manually annotated by BRENDA team
strain DSM 43297
UniProt
Manually annotated by BRENDA team
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Manually annotated by BRENDA team
Rhodotorula sp. AS2.2241
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Manually annotated by BRENDA team
strain Y379-50
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Manually annotated by BRENDA team
strain Y379-50
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Manually annotated by BRENDA team
gene adhB
UniProt
Manually annotated by BRENDA team
strain EbN1
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Manually annotated by BRENDA team
strain EbN1
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Manually annotated by BRENDA team
SUBSTRATE
PRODUCT                       
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate) hide
LITERATURE
(Substrate)
COMMENTARY
(Product) hide
LITERATURE
(Product)
Reversibility
r=reversible
ir=irreversible
?=not specified
(R)-1-phenylethanol + NAD+
1-phenylethanone + NADH + H+
show the reaction diagram
(R)-2-butanol + NAD+
2-butanone + NADH + H+
show the reaction diagram
Nocardia fusca AKU 2123
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6% of the activity with (RS)-2-hexanol
-
-
r
(R)-2-hexanol + NAD+
2-hexanone + NADH + H+
show the reaction diagram
Nocardia fusca AKU 2123
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30% of the activity with (RS)-2-hexanol
-
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r
(R)-2-pentanol + NAD+
2-pentanone + NADH + H+
show the reaction diagram
Nocardia fusca AKU 2123
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15% of the activity with (RS)-2-hexanol
-
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r
(R)-3-butyn-2-ol + NAD+
but-3-yn-2-one + NADH + H+
show the reaction diagram
Nocardia fusca AKU 2123
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0.5% of the activity with (RS)-2-hexanol
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-
r
(R)-3-pentyn-2-ol + NAD+
pent-3-yn-2-one + NADH + H+
show the reaction diagram
Nocardia fusca AKU 2123
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5.6% of the activity with (RS)-2-hexanol
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r
(S)-1,3-butanediol + NAD+ + H+
4-hydroxy-2-butanone + NADH
show the reaction diagram
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enantioselective oxidation of the (S)-isomer
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?
(S)-1-phenylethanol + NAD+
1 phenylethanone + NADH + H+
show the reaction diagram
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99% ethanoselective reaction
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r
(S)-1-phenylethanol + NAD+
acetophenone + NADH + H+
show the reaction diagram
(S)-2-butanol + NAD+
2-butanone + NADH + H+
show the reaction diagram
(S)-2-hexanol + NAD+
2-hexanone + NADH + H+
show the reaction diagram
(S)-2-pentanol + NAD+
2-pentanone + NADH + H+
show the reaction diagram
(S)-3-butyn-2-ol + NAD+
but-3-yn-2-one + NADH + H+
show the reaction diagram
Nocardia fusca AKU 2123
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6.9% of the activity with (RS)-2-hexanol
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r
(S)-3-pentyn-2-ol + NAD+
pent-3-yn-2-one + NADH + H+
show the reaction diagram
Nocardia fusca AKU 2123
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33% of the activity with (RS)-2-hexanol
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r
(S)-alpha-tetralol + NAD+
alpha-tetralone + NADH + H+
show the reaction diagram
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99% ethanoselective reaction
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r
1-hexanal + NADH + H+
hexan-1-ol + NAD+
show the reaction diagram
Nocardia fusca AKU 2123
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254% of the activity with (RS)-2-hexanol
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r
1-indanone + NADH + H+
(S)-1-indanol + NAD+
show the reaction diagram
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99% enantiomeric excess after 6 h at 50C
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?
2'-fluoroacetophenone + NADH + H+
(1S)-1-(2-fluorophenyl)ethanol + NAD+
show the reaction diagram
2,2,2-trifluoroacetophenone + NADH + H+
?
show the reaction diagram
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completely enantioselective reaction
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r
2,3-butanedione + NADH + H+
? + NAD+
show the reaction diagram
9% of the activity with ethyl 4-chloro-3-oxobutanoate
-
-
?
2,3-pentanedione + NADH + H+
? + NAD+
show the reaction diagram
82% of the activity with ethyl 4-chloro-3-oxobutanoate
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-
?
2-decanone + NADH + H+
(S)-2-decanol + NAD+
show the reaction diagram
Nocardia fusca AKU 2123
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159% of the activity with (RS)-2-hexanol
reaction is stereoselective
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r
2-heptanone + NADH + H+
(S)-2-heptanol + NAD+
show the reaction diagram
Nocardia fusca AKU 2123
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334% of the activity with (RS)-2-hexanol
reaction is stereoselective
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r
2-hexanone + NADH + H+
(S)-2-hexanol + NAD+
show the reaction diagram
Nocardia fusca AKU 2123
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225% of the activity with (RS)-2-hexanol
reaction is stereoselective
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r
2-octanone + NADH + H+
(S)-2-octanol + NAD+
show the reaction diagram
Nocardia fusca AKU 2123
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223% of the activity with (RS)-2-hexanol
reaction is stereoselective
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r
3'-fluoroacetophenone + NADH + H+
(1S)-1-(3-fluorophenyl)ethanol + NAD+
show the reaction diagram
4'-acetoxy acetophenone + NADH + H+
(1S)-1-(4-acetoxyphenyl)ethanol + NAD+
show the reaction diagram
4'-acetyl pyridine + NADH + H+
(1S)-1-(pyridin-4-yl)ethanol + NAD+
show the reaction diagram
4'-bromoacetophenone + NADH + H+
(1S)-1-(4-bromophenyl)ethanol + NAD+
show the reaction diagram
4'-chloroacetophenone + NADH + H+
(1S)-1-(4-chlorophenyl)ethanol + NAD+
show the reaction diagram
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83% of the activity with acetophenone
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-
?
4'-fluoroacetophenone + NADH + H+
(1S)-1-(4-fluorophenyl)ethanol + NAD+
show the reaction diagram
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117% of the activity with acetophenone
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?
4'-iodoacetophenone + NADH + H+
(1S)-1-(4-iodophenyl)ethanol + NAD+
show the reaction diagram
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31% of the activity with acetophenone
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?
6-methyl-5-hepten-2-one + NADH + H+
(S)-6-methyl-5-hepten-2-ol + NAD+
show the reaction diagram
Nocardia fusca AKU 2123
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188% of the activity with (RS)-2-hexanol
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r
acetophenone + NADH + H+
(1S)-1-phenylethanol + NAD+
show the reaction diagram
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enantiomeric excess of more than 99% for (S)-configuration of product
-
?
acetophenone + NADH + H+
(S)-1-phenylethanol + NAD+
show the reaction diagram
acetophenone + NADH + H+
alpha-phenylethanol + NAD+
show the reaction diagram
87% of the activity with phenylacetaldehyde
-
-
?
alpha-tetralone + NADH + H+
(S)-alpha-tetralol + NAD+
show the reaction diagram
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completely enantioselective reaction
99% enantiomeric excess after 6 h at 50C
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r
capronaldehyde + NADH + H+
n-hexanol + NAD+
show the reaction diagram
522% of the activity with phenylacetaldehyde
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?
ethyl (R)-4-chloro-3-hydroxybutanoate + NAD+
ethyl 4-chloro-3-oxobutanoate + NADH + H+
show the reaction diagram
Nocardia fusca AKU 2123
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38.1% of the activity with (RS)-2-hexanol
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r
ethyl 2-chloro-3-oxobutanoate + NADH + H+
ethyl 2-chloro-3-hydroxybutanoate + NAD+
show the reaction diagram
49% of the activity with ethyl 4-chloro-3-oxobutanoate
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?
ethyl 3-oxobutanoate + NADH + H+
ethyl 3-hydroxybutanoate + NAD+
show the reaction diagram
28% of the activity with ethyl 4-chloro-3-oxobutanoate
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?
ethyl 4-chloro-3-oxobutanoate + NADH + H+
ethyl (R)-4-chloro-3-hydroxybutanoate + NAD+
show the reaction diagram
ethyl 4-chloro-3-oxobutanoate + NADH + H+
ethyl (S)-4-chloro-3-hydroxybutanoate + NAD+
show the reaction diagram
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product in more than 99% enantiomeric excess
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?
n-valeraldehyde + NADH + H+
? + NAD+
show the reaction diagram
Nocardia fusca AKU 2123
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84% of the activity with (RS)-2-hexanol
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r
p-chloro-acetophenone + NADH + H+
alpha-(p-chlorophenyl)ethanol + NAD+
show the reaction diagram
288% of the activity with phenylacetaldehyde
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?
phenylacetaldehyde + NADH + H+
2-phenylethanol + NAD+
show the reaction diagram
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-
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?
pyruvic acid ethyl ester + NADH + H+
? + NAD+
show the reaction diagram
Nocardia fusca AKU 2123
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225% of the activity with (RS)-2-hexanol
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r
valeraldehyde + NADH + H+
n-pentanol + NAD+
show the reaction diagram
433% of the activity with phenylacetaldehyde
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?
additional information
?
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NATURAL SUBSTRATES
NATURAL PRODUCTS
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate) hide
LITERATURE
(Substrate)
COMMENTARY
(Product) hide
LITERATURE
(Product)
REVERSIBILITY
r=reversible
ir=irreversible
?=not specified
(S)-1-phenylethanol + NAD+
acetophenone + NADH + H+
show the reaction diagram
COFACTOR
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
NADPH
about 10% of the activity with NADH
additional information
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METALS and IONS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
EDTA
-
activates to 127% activity compared to the control activity at 1 mM and to 163% at 10 mM
K+
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activates to 167% activity compared to the control activity at 1 mM and to 193% at 100 mM
Li+
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activates to 127% activity compared to the control activity at 1 mM and to 178% at 100 mM
Na+
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activates to 179 at 100 mM
Zinc
sequence contains catalytic and structural zinc binding sites
Zn2+
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activates to 114% activity compared to the control activity at 1 mM
INHIBITORS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
(R)-1-phenylethanol
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(S)-1-phenylethanol
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strong substrate inhibition, 50% of maximum activity at 0.1 mM
1-butyl-3-methylimidazolium tetrafluoroborate
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65% inhibition at 2 mM
4-hydroxy mercuribenzoate
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2 mM, 5% residual activity
acetophenone
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inhibitory above 0.02 mM, 75% of maximum activty at 1 mM
AgNO3
Ca2+
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10% inhibition at 1 mM and 30% at 100 mM
CdCl2
Nocardia fusca AKU 2123
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2 mM, 6.6% residual activity
citrate
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2 mM, 28% residual activity
Co(NO3)2
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2 mM, 59% residual activity
Cu2+
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23% inhibition at 1 mM
CuSO4
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2 mM, complete inhibition
D-Cysteine
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2 mM, 8% residual activity
diethyldicarbonate
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2 mM, 30% residual activity
FeCl3
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2 mM, 2% residual activity
glutathione
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2 mM, 31% residual activity
guanidinium hydrochloride
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1 M, 1.5% residual activity
Hg2+
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67% inhibition at 1 mM
HgCl2
Nocardia fusca AKU 2123
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2 mM, no residual activity
hydroxylamine
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2 mM, 23% residual activity
Hydroxyquinoline
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2 mM, 18% residual activity
iodoacetate
L-cysteine
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2 mM, 12% residual activity
Mg2+
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33% inhibition at 100 mM
MgCl2
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2 mM, 75% residual activity
MnSO4
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2 mM, 53% residual activity
N-ethylmaleimide
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2 mM, 5% residual activity
NiCl2
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2 mM, 24% residual activity
o-phenanthroline
oxalate
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2 mM, 26% residual activity
Pb(OAc)2
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2 mM, 8% residual activity
phenyl methyl sulfonylfluoride
5 mM, 49% residual activity
potassium iodide
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1 M, 1.4% residual activity
Sodium azide
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2 mM, 35% residual activity
sodium dodecylsulfate
tartarate
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2 mM, 21% residual activity
Triton X-100
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1% w/v, 67% residual activity
trypaflavine
Nocardia fusca AKU 2123
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1 mM, 7.7% residual activity
Tween 80
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1% w/v, 26.5% residual activity
Urea
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1 M, 5.8% residual activity
ZnSO4
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2 mM, 2% residual activity
additional information
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ACTIVATING COMPOUND
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
2-mercaptoethanol
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2 mM, 115% of initial activity
o-phenanthroline
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activates to 108% activity compared to the control activity at 0.1 mM and to 109% at 1 mM
KM VALUE [mM]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
4.2
(S)-1-indanol
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pH 6.0, 65C, recombinant enzyme, reduction reaction
0.0055
(S)-1-phenylethanol
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pH 7.8, 25C
0.012 - 29.8
(S)-2-butanol
0.33
(S)-2-hexanol
Nocardia fusca AKU 2123
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30C, pH 7.5
0.07 - 8.8
(S)-2-pentanol
1.6
(S)-3-pentyn-2-ol
Nocardia fusca AKU 2123
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30C, pH 7.5
27.6
1-Indanone
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pH 6.0, 65C, recombinant enzyme, reduction reaction
2.5
2-Hexanone
Nocardia fusca AKU 2123
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30C, pH 7.5
0.0113 - 0.153
acetophenone
5.8
alpha-tetralone
-
pH 6.0, 65C, recombinant enzyme, reduction reaction
3.3
ethyl 4-chloro-3-oxobutanoate
pH 6.0, 30C
0.157
NADH
-
pH 7.0, 25C
5.1
rac-1-indanol
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pH 6.0, 65C, recombinant enzyme, reduction reaction
5.3
rac-alpha-tetralol
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pH 6.0, 65C, recombinant enzyme, reduction reaction
additional information
additional information
-
TURNOVER NUMBER [1/s]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
61.4
(S)-1-indanol
Thermus thermophilus
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pH 6.0, 65C, recombinant enzyme, reduction reaction
1.2 - 4.8
(S)-2-butanol
2.6 - 6.7
(S)-2-pentanol
8.3
1-Indanone
Thermus thermophilus
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pH 6.0, 65C, recombinant enzyme, reduction reaction
7.7
alpha-tetralone
Thermus thermophilus
-
pH 6.0, 65C, recombinant enzyme, reduction reaction
45.7
rac-1-indanol
Thermus thermophilus
-
pH 6.0, 65C, recombinant enzyme, reduction reaction
48.1
rac-alpha-tetralol
Thermus thermophilus
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pH 6.0, 65C, recombinant enzyme, reduction reaction
SPECIFIC ACTIVITY [µmol/min/mg]
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
1.5
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immobilized recombinant enzyme
41.5
Nocardia fusca AKU 2123
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30C, pH 7.5
151.1
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substrate: (S)-1-phenylethanol
358.6
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pH 7.0, 25C
pH OPTIMUM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
10
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oxidation reaction
pH RANGE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
5.5 - 6.5
Nocardia fusca AKU 2123
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reduction reaction
5.5 - 7
more than 80% of maximum activity within
6 - 7.7
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reduction reaction, high activity
6.5 - 7
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more than 80% of maximum activity
8.5 - 9.5
Nocardia fusca AKU 2123
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oxidation reaction
9 - 10
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oxidation reaction, high activity
TEMPERATURE OPTIMUM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
TEMPERATURE RANGE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
20
-
54% of maximum activity
25 - 35
more than 80% of maximum activity within
25 - 73
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the enzyme displays activity at temperatures up to 73C
50
no residual activity
75
-
61% of maximum activity
LOCALIZATION
ORGANISM
UNIPROT
COMMENTARY hide
GeneOntology No.
LITERATURE
SOURCE
MOLECULAR WEIGHT
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
59000
-
gel filtration
71000
-
about, recombinant enzyme, gel filtration in absence of NaCl
105000
-
about, recombinant enzyme, gel filtration in presence of 0.15 M NaCl
120000
-
gel filtration
140000
-
recombinant enzyme, gel filtration
150000
Nocardia fusca AKU 2123
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gel filtration
SUBUNITS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
?
x * 36026, calculated, x * 39000, SDS-PAGE
tetramer
Crystallization/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
apo-enzyme and bound to NAD+, at a resolution of 2.1 and 2.4 A, respectively. Enzyme is a tetamer with two types of hydrophobic interfaces. NAD+-binding is associated with a conformational shift of the substrate binding loop from a crystallographically unordered open to a more ordered closed form
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pH STABILITY
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
5.5 - 9.5
Nocardia fusca AKU 2123
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30 min, 30C, more than 90% residual activity
685643
5.6
between pH 5.6-7.0, 4C, stable for 48 h
724568
TEMPERATURE STABILITY
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
25
-
phosphate buffer, pH 7.0, 7 h, 80% residual activity
40
Nocardia fusca AKU 2123
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30 min, pH 7.0, 85% residual activity
60
-
24 h, purified recombinant enzyme, 134% inactivation
additional information
-
the thermal stability of the enzyme adsorbed by ionic exchange is very similar to the stability of the covalently immobilized enzymes in the pH range 5-9, thermal inactivation kinetics, overview
ORGANIC SOLVENT
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
dimethyl formamide
dimethyl sulfoxide
dioxane
Ethanol
isopropanol
Pyridine
tetrahydrofuran
additional information
-
the enzyme shows a good tolerance to common organic solvents
STORAGE STABILITY
ORGANISM
UNIPROT
LITERATURE
-20C, phosphate buffer, pH 7.0, presence of 2-mercaptoethanol and phenylmethyl sulfonylfluoride, stable for at least 3 months
-
Purification/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
by heat treatment at 70C and/or adsorption chromatography on an IDA-Cu2+ support, both methods combined result in 8.8fold purification
-
recombinant enzyme
recombinant enzyme 11fold to homogeneity from Escherichia coli strain BL21(DE3) by heat denaturation of host proteins, anion exchange chromatography and gel filtration
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recombinant protein
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Cloned/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
expressed in Escherichia coli RB791 cells
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expression in Escherichia coli
expression in Escherichia coli strain BL21(DE3)
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ENGINEERING
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
W95L/N249Y
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the mutant exhibits higher activity but decreased affinity toward aliphatic alcohols, aldehydes as well as NAD+ and NADH compared to the wild type enzyme, optimum pH is at about pH 8.6
I86A
site-directed mutagensis, the secondary alcohol dehydrogenase I86A mutant is stereospecific for (R)-alcohols instead of (S)-alcohols, in contrast to the wild-type enzyme, the mutation I86A allows large substituents to fit into the large pocket of I86ATeSADH, which corresponds to the small pocket in wild-type TeSADH, modeling of the stereopreference of TeSADH I86A
additional information
-
covalent immobilization of the purified recombinant enzyme on different supports, i.e. on glyoxyl agarose, amino epoxy agarose, CNBr-activated sepharose, monoaminoethyl-N-ethylagarose-glutaraldehyde, monoaminoethyl-N-ethyl agarose, or polyethyleneimine agarose, immobilized enzyme activities, overview
APPLICATION
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
synthesis