Information on EC 1.1.1.192 - long-chain-alcohol dehydrogenase

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

EC NUMBER
COMMENTARY hide
1.1.1.192
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RECOMMENDED NAME
GeneOntology No.
long-chain-alcohol dehydrogenase
REACTION
REACTION DIAGRAM
COMMENTARY hide
ORGANISM
UNIPROT
LITERATURE
a long-chain alcohol + 2 NAD+ + H2O = a long-chain carboxylate + 2 NADH + 2 H+
show the reaction diagram
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REACTION TYPE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
oxidation
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redox reaction
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reduction
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PATHWAY
BRENDA Link
KEGG Link
MetaCyc Link
Fatty acid degradation
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SYSTEMATIC NAME
IUBMB Comments
long-chain-alcohol:NAD+ oxidoreductase
Hexadecanol is a good substrate.
CAS REGISTRY NUMBER
COMMENTARY hide
76774-36-2
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ORGANISM
COMMENTARY hide
LITERATURE
UNIPROT
SEQUENCE DB
SOURCE
horse
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Manually annotated by BRENDA team
GSV224, gene nosE
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Manually annotated by BRENDA team
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Manually annotated by BRENDA team
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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
(2S)-5-hydroxy-2-aminovaleric acid + NAD+ + H2O
(2S)-2-amino-5-oxopentanoate + NADH
show the reaction diagram
-
no activity with the (2R)-isomer
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-
?
(2S,4S)-5-hydroxyleucine + NAD+ + H2O
(4S)-5-oxo-L-leucine + NADH
show the reaction diagram
1,3-propanediol + 2 NAD+ + H2O
? + 2 NADH + 2 H+
show the reaction diagram
1-decanol + 2 NAD+ + H2O
decanoic acid + 2 NADH + 2 H+
show the reaction diagram
1-dodecanol + 2 NAD+ + H2O
dodecanoic acid + 2 NADH + 2 H+
show the reaction diagram
1-eicosanol + 2 NAD+ + H2O
eicosanoic acid + 2 NADH + 2 H+
show the reaction diagram
1-hexadecanol + 2 NAD+ + H2O
hexadecanoic acid + 2 NADH + 2 H+
show the reaction diagram
1-octacosanol + 2 NAD+ + H2O
octacosanoic acid + 2 NADH + 2 H+
show the reaction diagram
1-octadecanol + 2 NAD+ + H2O
octadecanoic acid + 2 NADH + 2 H+
show the reaction diagram
1-octanol + 2 NAD+ + H2O
octanoic acid + 2 NADH + 2 H+
show the reaction diagram
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-
-
r
1-octanol + 2 NADP+ + H2O
octanoic acid + 2 NADPH + 2 H+
show the reaction diagram
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-
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r
1-tetracosanol + 2 NAD+ + H2O
tetracosanoic acid + 2 NADH + 2 H+
show the reaction diagram
1-tetradecanol + 2 NAD+ + H2O
tetradecanoic acid + 2 NADH + 2 H+
show the reaction diagram
12-hydroxydodecanoic acid + NAD+ + H2O
? + NADH
show the reaction diagram
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-
-
-
?
decanal + NAD+ + H+
decanoic acid + NADH
show the reaction diagram
about 10% of the activity with 1-octanol
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r
dodecanal + NAD+ + H+
dodecanoic acid + NADH
show the reaction diagram
about 10% of the activity with 1-octanol
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r
ethanol + NAD+ + H2O
ethanal + NADH
show the reaction diagram
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-
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?
glycerol + 2 NAD+ + H2O
? + 2 NADH + 2 H+
show the reaction diagram
about 45% of the activity with ethanol
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r
hexadecanol + NAD+ + H2O
hexadecanal + NADH
show the reaction diagram
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?
isopropanol + 2 NAD+ + H2O
? + 2 NADH + 2 H+
show the reaction diagram
about 15% of the activity with 1-octanol
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r
long-chain alcohol + NAD+ + H2O
long-chain carboxylate + NADH
show the reaction diagram
n-butanol + NAD+ + H2O
n-butanal + NADH
show the reaction diagram
n-decanol + NAD+ + H2O
n-decanal + NADH
show the reaction diagram
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-
-
-
r
n-heptanol + NAD+ + H2O
n-heptanal + NADH
show the reaction diagram
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-
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?
n-hexanol + NAD+ + H2O
n-hexanal + NADH
show the reaction diagram
n-nonanol + NAD+ + H2O
n-nonanal + NADH
show the reaction diagram
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-
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?
n-octanol + NAD+ + H2O
n-octanal + NADH
show the reaction diagram
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?
n-pentanol + NAD+ + H2O
n-pentanal + NADH
show the reaction diagram
n-propanol + NAD+ + H2O
n-propanal + NADH
show the reaction diagram
octanal + NAD+ + H2O
octanoic acid + NADH + H+
show the reaction diagram
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r
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
(2S,4S)-5-hydroxyleucine + NAD+ + H2O
(4S)-5-oxo-L-leucine + NADH
show the reaction diagram
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enzyme reaction is part of the biosynthesis of (2S,4S)-4-methylproline
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r
long-chain alcohol + NAD+ + H2O
long-chain carboxylate + NADH
show the reaction diagram
COFACTOR
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
NADP+
NAD+ is prefered over NADP+; NADP+ is prefered over NAD+
METALS and IONS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
Fe2+
1 mM, 136% of initial activity; 1 mM, 168% of initial activity
Na+
1 mM, 110% of initial activity
Zn2+
-
dependent on
additional information
INHIBITORS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
1,10-phenanthroline
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Al3+
1 mM, 14.7% residual activity; 1 mM, 18.9% residual activity
Ca2+
1 mM, no residual activity
Co2+
1 mM, 51.9% residual activity; 1 mM, 68.7% residual activity
Cu2+
1 mM, 14.0% residual activity; 1 mM, 44.2% residual activity
K+
1 mM, 70.3% residual activity; 1 mM, 82.3% residual activity
Mg2+
1 mM, 0.3% residual activity; 1 mM, 74.3% residual activity
Mn2+
1 mM, 14.3% residual activity; 1 mM, 23.4% residual activity
N-ethylmaleimide
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Ni2+
1 mM, 18.2% residual activity; 1 mM, 72.7% residual activity
sodium dodecylsulfate
1 mM, 3% residual activity; 1 mM, no residual activity
Zn2+
1 mM, 14.1% residual activity; 1 mM, 30.5% residual activity
additional information
ACTIVATING COMPOUND
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
albumin
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0.5 mg/ml increases reaction rate
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EDTA
1 mM, 105% of initial activity
KM VALUE [mM]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
1.2
(2S)-5-hydroxy-2-aminovaleric acid
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pH 10.0, 42C, recombinant enzyme
0.24
(2S,4S)-5-hydroxyleucine
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pH 10.0, 42C, recombinant enzyme
3.4
1-Hexanol
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1.2 - 3.88
1-Octanol
26.5
1-Pentanol
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324
1-propanol
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1.7
12-Hydroxydodecanoic acid
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0.00067
hexadecanol
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0.044
n-butanol
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0.095
n-decanal
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0.23
n-decanol
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0.26
n-Heptanol
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0.14
n-Hexanol
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0.36
n-nonanol
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0.34
n-Octanol
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0.18
n-Pentanol
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0.053
n-Propanol
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0.31 - 1.44
NAD+
0.17
NADH
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2.4
NADP+
cosubstrate 1-octanol, pH 8.0, 60C
0.84
NADPH
cosubstrate octanal, pH 8.0, 60C
1.15
octanal
cosubstrate NADPH, pH 8.0, 60C
TURNOVER NUMBER [1/s]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
38.5
NAD+
Geobacillus thermodenitrificans
A4IP64, A4ISB9
cosubstrate 1-octanol, pH 8.0, 60C
283.1
NADP+
Geobacillus thermodenitrificans
A4IP64, A4ISB9
cosubstrate 1-octanol, pH 8.0, 60C
4808
NADPH
Geobacillus thermodenitrificans
A4IP64, A4ISB9
cosubstrate octanal, pH 8.0, 60C
kcat/KM VALUE [1/mMs-1]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
67.2
1-Octanol
Geobacillus thermodenitrificans
A4IP64, A4ISB9
cosubstrate NADP+, pH 8.0, 60C
1228
26.7
NAD+
Geobacillus thermodenitrificans
A4IP64, A4ISB9
cosubstrate 1-octanol, pH 8.0, 60C
7
117.9
NADP+
Geobacillus thermodenitrificans
A4IP64, A4ISB9
cosubstrate 1-octanol, pH 8.0, 60C
10
5724
NADPH
Geobacillus thermodenitrificans
A4IP64, A4ISB9
cosubstrate octanal, pH 8.0, 60C
5
450.8
octanal
Geobacillus thermodenitrificans
A4IP64, A4ISB9
cosubstrate NADPH, pH 8.0, 60C
837
pH OPTIMUM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
7
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n-decanol, reduction of
8.4
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hexadecanol, diphosphate buffer
8.8 - 9
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hexadecanol, glycine or barbital buffer
9.5
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n-decanol, oxidation of
pH RANGE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
TEMPERATURE OPTIMUM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
37
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assay at
SOURCE TISSUE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
SOURCE
MOLECULAR WEIGHT
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
117000 - 120000
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PAGE, gel filtration
163000
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gel filtration
SUBUNITS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
?
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x * 35000, about, recombinant enzyme, SDS-PAGE
octamer
tetramer
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4 * 40000, SDS-PAGE
trimer
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3 * 40000, SDS-PAGE
additional information
Crystallization/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
TEMPERATURE STABILITY
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
50
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stable up to
60
14 h, more than 50% of initial activity; 14 h, more than 50% of initial activity
70
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10 min, all activity lost
GENERAL STABILITY
ORGANISM
UNIPROT
LITERATURE
dithiothreitol, 2 mM, no stabilization, crude extract
ethylene glycol, 20% w/w, no stabilization, crude extract
solubilization with 1% Tween 80 or Triton X-100 at 4C stimulates inactivation, crude extract
Purification/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
recombinant His-tagged enzyme by nickel affinity chromatography
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Cloned/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
expression in Escherichia coli; expression in Escherichia coli
gene nosE, overexpression in Escherichia coli BL21(DE3) as N-terminally His-tagged enzyme
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