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
1.1.1.192
-
RECOMMENDED NAME
GeneOntology No.
long-chain-alcohol dehydrogenase
REACTION
REACTION DIAGRAM
COMMENTARY
ORGANISM
UNIPROT ACCESSION NO.
LITERATURE
a long-chain alcohol + 2 NAD+ + H2O = a long-chain carboxylate + 2 NADH + 2 H+
show the reaction diagram
-
-
-
-
REACTION TYPE
ORGANISM
UNIPROT ACCESSION NO.
COMMENTARY
LITERATURE
oxidation
-
-
-
-
redox reaction
-
-
-
-
reduction
-
-
-
-
PATHWAY
KEGG Link
MetaCyc Link
Fatty acid degradation
-
SYSTEMATIC NAME
IUBMB Comments
long-chain-alcohol:NAD+ oxidoreductase
Hexadecanol is a good substrate.
SYNONYMS
ORGANISM
UNIPROT ACCESSION NO.
COMMENTARY
LITERATURE
dehydrogenase, long-chain alcohol
-
-
-
-
fatty alcohol oxidoreductase
-
-
-
-
long-chain alcohol dehydrogenase
-
-
-
-
long-chain alkyl alcohol dehydrogenase
A4IP64, A4ISB9
-
long-chain alkyl alcohol dehydrogenase
A4IP64, A4ISB9
-
-
long-chain dehydrogenase
-
-
CAS REGISTRY NUMBER
COMMENTARY
76774-36-2
-
SUBSTRATE
PRODUCT                      
REACTION DIAGRAM
ORGANISM
UNIPROT ACCESSION NO.
COMMENTARY
(Substrate)
LITERATURE
(Substrate)
COMMENTARY
(Product)
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
-
-
?
(2S,4S)-5-hydroxyleucine + NAD+ + H2O
(4S)-5-oxo-L-leucine + NADH
show the reaction diagram
-
-, enzyme reaction is part of the biosynthesis of (2S,4S)-4-methylproline
-
-
r
1,3-propanediol + 2 NAD+ + H2O
? + 2 NADH + 2 H+
show the reaction diagram
A4IP64, A4ISB9
about 45% of the activity with ethanol
-
-
r
1,3-propanediol + 2 NAD+ + H2O
? + 2 NADH + 2 H+
show the reaction diagram
A4IP64, A4ISB9
about 5% of the activity with 1-octanol
-
-
r
1-decanol + 2 NAD+ + H2O
decanoic acid + 2 NADH + 2 H+
show the reaction diagram
A4IP64, A4ISB9
about 20% of the activity with ethanol
-
-
r
1-decanol + 2 NAD+ + H2O
decanoic acid + 2 NADH + 2 H+
show the reaction diagram
A4IP64, A4ISB9
about 50% of the activity with 1-octanol
-
-
r
1-dodecanol + 2 NAD+ + H2O
dodecanoic acid + 2 NADH + 2 H+
show the reaction diagram
A4IP64, A4ISB9
about 17% of the activity with ethanol
-
-
r
1-dodecanol + 2 NAD+ + H2O
dodecanoic acid + 2 NADH + 2 H+
show the reaction diagram
A4IP64, A4ISB9
about 30% of the activity with 1-octanol
-
-
r
1-eicosanol + 2 NAD+ + H2O
eicosanoic acid + 2 NADH + 2 H+
show the reaction diagram
A4IP64, A4ISB9
about 25% of the activity with 1-octanol
-
-
r
1-eicosanol + 2 NAD+ + H2O
eicosanoic acid + 2 NADH + 2 H+
show the reaction diagram
A4IP64, A4ISB9
about 3% of the activity with ethanol
-
-
r
1-hexadecanol + 2 NAD+ + H2O
hexadecanoic acid + 2 NADH + 2 H+
show the reaction diagram
A4IP64, A4ISB9
about 10% of the activity with ethanol
-
-
r
1-hexadecanol + 2 NAD+ + H2O
hexadecanoic acid + 2 NADH + 2 H+
show the reaction diagram
A4IP64, A4ISB9
about 25% of the activity with 1-octanol
-
-
r
1-octacosanol + 2 NAD+ + H2O
octacosanoic acid + 2 NADH + 2 H+
show the reaction diagram
A4IP64, A4ISB9
about 40% of the activity with ethanol
-
-
r
1-octacosanol + 2 NAD+ + H2O
octacosanoic acid + 2 NADH + 2 H+
show the reaction diagram
A4IP64, A4ISB9
about 5% of the activity with 1-octanol
-
-
r
1-octadecanol + 2 NAD+ + H2O
octadecanoic acid + 2 NADH + 2 H+
show the reaction diagram
A4IP64, A4ISB9
about 15% of the activity with 1-octanol
-
-
r
1-octadecanol + 2 NAD+ + H2O
octadecanoic acid + 2 NADH + 2 H+
show the reaction diagram
A4IP64, A4ISB9
about 5% of the activity with ethanol
-
-
r
1-octanol + 2 NAD+ + H2O
octanoic acid + 2 NADH + 2 H+
show the reaction diagram
A4IP64, A4ISB9
-
-
-
r
1-octanol + 2 NADP+ + H2O
octanoic acid + 2 NADPH + 2 H+
show the reaction diagram
A4IP64, A4ISB9
-
-
-
r
1-tetracosanol + 2 NAD+ + H2O
tetracosanoic acid + 2 NADH + 2 H+
show the reaction diagram
A4IP64, A4ISB9
about 10% of the activity with 1-octanol
-
-
r
1-tetracosanol + 2 NAD+ + H2O
tetracosanoic acid + 2 NADH + 2 H+
show the reaction diagram
A4IP64, A4ISB9
about 30% of the activity with ethanol
-
-
r
1-tetradecanol + 2 NAD+ + H2O
tetradecanoic acid + 2 NADH + 2 H+
show the reaction diagram
A4IP64, A4ISB9
about 15% of the activity with ethanol
-
-
r
1-tetradecanol + 2 NAD+ + H2O
tetradecanoic acid + 2 NADH + 2 H+
show the reaction diagram
A4IP64, A4ISB9
about 30% of the activity with 1-octanol
-
-
r
12-hydroxydodecanoic acid + NAD+ + H2O
? + NADH
show the reaction diagram
-
-
-
-
?
decanal + NAD+ + H+
decanoic acid + NADH
show the reaction diagram
A4IP64, A4ISB9
about 10% of the activity with 1-octanol
-
-
r
dodecanal + NAD+ + H+
dodecanoic acid + NADH
show the reaction diagram
A4IP64, A4ISB9
about 10% of the activity with 1-octanol
-
-
r
ethanol + NAD+ + H2O
ethanal + NADH
show the reaction diagram
-
-
-
-
?
glycerol + 2 NAD+ + H2O
? + 2 NADH + 2 H+
show the reaction diagram
A4IP64, A4ISB9
about 45% of the activity with ethanol
-
-
r
hexadecanol + NAD+ + H2O
hexadecanal + NADH
show the reaction diagram
-
-
-
-
?
isopropanol + 2 NAD+ + H2O
? + 2 NADH + 2 H+
show the reaction diagram
A4IP64, A4ISB9
about 15% of the activity with 1-octanol
-
-
r
long-chain alcohol + NAD+ + H2O
long-chain carboxylate + NADH
show the reaction diagram
-
C6-C18 alcohols
-
-
-
long-chain alcohol + NAD+ + H2O
long-chain carboxylate + NADH
show the reaction diagram
-
maximal activity with decanol
-
-
-
long-chain alcohol + NAD+ + H2O
long-chain carboxylate + NADH
show the reaction diagram
-
maximal activity with decanol
-
-
-
long-chain alcohol + NAD+ + H2O
long-chain carboxylate + NADH
show the reaction diagram
-
long chain n-alcanols up to C12
-
-
r
long-chain alcohol + NAD+ + H2O
long-chain carboxylate + NADH
show the reaction diagram
-
C17-C-19 alcohols do not serve as a good substrate
-
-
-
long-chain alcohol + NAD+ + H2O
long-chain carboxylate + NADH
show the reaction diagram
-
maximum activity on C14 alcohol
-
-
-
long-chain alcohol + NAD+ + H2O
long-chain carboxylate + NADH
show the reaction diagram
-
C8-C16
-
-
-
long-chain alcohol + NAD+ + H2O
long-chain carboxylate + NADH
show the reaction diagram
-
C10-C18, enzyme may play an important role in regulating the cellular levels of ether-linked lipids
-
-
-
long-chain alcohol + NAD+ + H2O
long-chain carboxylate + NADH
show the reaction diagram
-
peroxisomal enzyme is participating in fatty acid degradation
-
-
-
long-chain alcohol + NAD+ + H2O
long-chain carboxylate + NADH
show the reaction diagram
-
peroxisomal enzyme is participating in fatty acid degradation
-
-
-
long-chain alcohol + NAD+ + H2O
long-chain carboxylate + NADH
show the reaction diagram
-
microsomal and mitochondrial enzyme may have an indispensable role in lipid biosynthesis
-
-
-
long-chain alcohol + NAD+ + H2O
long-chain carboxylate + NADH
show the reaction diagram
-
microsomal and mitochondrial enzyme may have an indispensable role in lipid biosynthesis
-
-
-
n-butanol + NAD+ + H2O
n-butanal + 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
-
-
-
-
r
n-heptanol + NAD+ + H2O
n-heptanal + NADH
show the reaction diagram
-
-
-
-
?
n-hexanol + NAD+ + H2O
n-hexanal + NADH
show the reaction diagram
-
-
-
-
?
n-hexanol + NAD+ + H2O
n-hexanal + NADH
show the reaction diagram
-
-
-
-
-
n-nonanol + NAD+ + H2O
n-nonanal + NADH
show the reaction diagram
-
-
-
-
?
n-octanol + NAD+ + H2O
n-octanal + NADH
show the reaction diagram
-
-
-
-
?
n-pentanol + NAD+ + H2O
n-pentanal + NADH
show the reaction diagram
-
-
-
-
?
n-pentanol + NAD+ + H2O
n-pentanal + NADH
show the reaction diagram
-
-
-
-
-
n-propanol + NAD+ + H2O
n-propanal + 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
A4IP64, A4ISB9
-
-
-
r
long-chain alcohol + NAD+ + H2O
long-chain carboxylate + NADH
show the reaction diagram
-
enzyme also uses formaldehyde and short chain aliphatic alcohols
-
-
-
additional information
?
-
-
stereospecific abstraction of the 5pro-S hydrogen
-
-
-
additional information
?
-
A4IP64, A4ISB9
substrates are a broad range of alkyl alcohols from ethanol to 1-triacontanol
-
-
-
NATURAL SUBSTRATES
NATURAL PRODUCTS
REACTION DIAGRAM
ORGANISM
UNIPROT ACCESSION NO.
COMMENTARY
(Substrate)
LITERATURE
(Substrate)
COMMENTARY
(Product)
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
-
enzyme reaction is part of the biosynthesis of (2S,4S)-4-methylproline
-
-
r
long-chain alcohol + NAD+ + H2O
long-chain carboxylate + NADH
show the reaction diagram
-
enzyme may play an important role in regulating the cellular levels of ether-linked lipids
-
-
-
long-chain alcohol + NAD+ + H2O
long-chain carboxylate + NADH
show the reaction diagram
-
peroxisomal enzyme is participating in fatty acid degradation
-
-
-
long-chain alcohol + NAD+ + H2O
long-chain carboxylate + NADH
show the reaction diagram
-
peroxisomal enzyme is participating in fatty acid degradation
-
-
-
long-chain alcohol + NAD+ + H2O
long-chain carboxylate + NADH
show the reaction diagram
-
microsomal and mitochondrial enzyme may have an indispensable role in lipid biosynthesis
-
-
-
long-chain alcohol + NAD+ + H2O
long-chain carboxylate + NADH
show the reaction diagram
-
microsomal and mitochondrial enzyme may have an indispensable role in lipid biosynthesis
-
-
-
long-chain alcohol + NAD+ + H2O
long-chain carboxylate + NADH
show the reaction diagram
-
enzyme also uses formaldehyde and short chain aliphatic alcohols
-
-
-
COFACTOR
ORGANISM
UNIPROT ACCESSION NO.
COMMENTARY
LITERATURE
IMAGE
NAD+
-
absolute requirement
NAD+
-
absolute requirement
NAD+
-
specific for the A-side of NAD+, no activity with NADP+
NAD+
A4IP64, A4ISB9
NAD+ is prefered over NADP+; NADP+ is prefered over NAD+
NADP+
A4IP64, A4ISB9
NAD+ is prefered over NADP+; NADP+ is prefered over NAD+
METALS and IONS
ORGANISM
UNIPROT ACCESSION NO.
COMMENTARY
LITERATURE
Na+
A4IP64, A4ISB9
1 mM, 110% of initial activity
Zinc
-
6.1 atoms/enzyme molecule
Zinc
-
1.1 mol per mol of subunit
Zn2+
-
dependent on
Fe2+
A4IP64, A4ISB9
1 mM, 136% of initial activity; 1 mM, 168% of initial activity
additional information
A4IP64, A4ISB9
enzyme contains neither Fe nor other metals, and Fe is not required for the activity, although sequence analysis reveals that ADH1 belongs to the Fe-containing/activated long-chain alcohol dehydrogenases; enzyme contains neither Fe nor other metals, and Fe is not required for the activity, although sequence analysis reveals that ADH1 belongs to the Fe-containing/activated long-chain alcohol dehydrogenases
INHIBITORS
ORGANISM
UNIPROT ACCESSION NO.
COMMENTARY
LITERATURE
IMAGE
1,10-phenanthroline
-
-
Al3+
A4IP64, A4ISB9
1 mM, 14.7% residual activity; 1 mM, 18.9% residual activity
Ca2+
A4IP64, A4ISB9
1 mM, no residual activity
Co2+
A4IP64, A4ISB9
1 mM, 51.9% residual activity; 1 mM, 68.7% residual activity
Cu2+
A4IP64, A4ISB9
1 mM, 14.0% residual activity; 1 mM, 44.2% residual activity
K+
A4IP64, A4ISB9
1 mM, 70.3% residual activity; 1 mM, 82.3% residual activity
Mg2+
A4IP64, A4ISB9
1 mM, 0.3% residual activity; 1 mM, 74.3% residual activity
N-ethylmaleimide
-
-
Ni2+
A4IP64, A4ISB9
1 mM, 18.2% residual activity; 1 mM, 72.7% residual activity
sodium dodecylsulfate
A4IP64, A4ISB9
1 mM, 3% residual activity; 1 mM, no residual activity
Zn2+
A4IP64, A4ISB9
1 mM, 14.1% residual activity; 1 mM, 30.5% residual activity
Mn2+
A4IP64, A4ISB9
1 mM, 14.3% residual activity; 1 mM, 23.4% residual activity
additional information
-
inhibition differs for ethanol and formaldehyde as substrates
-
additional information
-
not: pyrazole, sodium azide, AMP, ATP, quinacrine, iodoacetate
-
ACTIVATING COMPOUND
ORGANISM
UNIPROT ACCESSION NO.
COMMENTARY
LITERATURE
IMAGE
Albumin
-
0.5 mg/ml increases reaction rate
-
EDTA
A4IP64, A4ISB9
1 mM, 105% of initial activity
KM VALUE [mM]
KM VALUE [mM] Maximum
SUBSTRATE
ORGANISM
UNIPROT ACCESSION NO.
COMMENTARY
LITERATURE
IMAGE
1.2
-
(2S)-5-hydroxy-2-aminovaleric acid
-
pH 10.0, 42C, recombinant enzyme
0.24
-
(2S,4S)-5-hydroxyleucine
-
pH 10.0, 42C, recombinant enzyme
3.88
-
1-Octanol
A4IP64, A4ISB9
cosubstrate NADP+, pH 8.0, 60C
26.5
-
1-Pentanol
-
-
1.7
-
12-Hydroxydodecanoic acid
-
-
0.00067
-
hexadecanol
-
-
0.044
-
n-butanol
-
-
0.095
-
n-decanal
-
-
0.23
-
n-decanol
-
-
0.26
-
n-Heptanol
-
-
0.14
-
n-Hexanol
-
-
0.36
-
n-nonanol
-
-
0.34
-
n-Octanol
-
-
0.18
-
n-Pentanol
-
-
0.053
-
n-Propanol
-
-
1.44
-
NAD+
A4IP64, A4ISB9
cosubstrate 1-octanol, pH 8.0, 60C
2.4
-
NADP+
A4IP64, A4ISB9
cosubstrate 1-octanol, pH 8.0, 60C
0.84
-
NADPH
A4IP64, A4ISB9
cosubstrate octanal, pH 8.0, 60C
1.15
-
Octanal
A4IP64, A4ISB9
cosubstrate NADPH, pH 8.0, 60C
TURNOVER NUMBER [1/s]
TURNOVER NUMBER MAXIMUM[1/s]
SUBSTRATE
ORGANISM
UNIPROT ACCESSION NO.
COMMENTARY
LITERATURE
IMAGE
38.5
-
NAD+
A4IP64, A4ISB9
cosubstrate 1-octanol, pH 8.0, 60C
283.1
-
NADP+
A4IP64, A4ISB9
cosubstrate 1-octanol, pH 8.0, 60C
4808
-
NADPH
A4IP64, A4ISB9
cosubstrate octanal, pH 8.0, 60C
kcat/KM VALUE [1/mMs-1]
kcat/KM VALUE [1/mMs-1] Maximum
SUBSTRATE
ORGANISM
UNIPROT ACCESSION NO.
COMMENTARY
LITERATURE
IMAGE
67.2
-
1-Octanol
A4IP64, A4ISB9
cosubstrate NADP+, pH 8.0, 60C
1163
26.7
-
NAD+
A4IP64, A4ISB9
cosubstrate 1-octanol, pH 8.0, 60C
14330
117.9
-
NADP+
A4IP64, A4ISB9
cosubstrate 1-octanol, pH 8.0, 60C
27497
5724
-
NADPH
A4IP64, A4ISB9
cosubstrate octanal, pH 8.0, 60C
27498
450.8
-
Octanal
A4IP64, A4ISB9
cosubstrate NADPH, pH 8.0, 60C
14758
pH OPTIMUM
pH MAXIMUM
ORGANISM
UNIPROT ACCESSION NO.
COMMENTARY
LITERATURE
7
-
-
n-decanol, reduction of
8.4
-
-
hexadecanol, diphosphate buffer
8.8
9
-
hexadecanol, glycine or barbital buffer
9.5
-
-
n-decanol, oxidation of
10
-
-
-
pH RANGE
pH RANGE MAXIMUM
ORGANISM
UNIPROT ACCESSION NO.
COMMENTARY
LITERATURE
TEMPERATURE OPTIMUM
TEMPERATURE OPTIMUM MAXIMUM
ORGANISM
UNIPROT ACCESSION NO.
COMMENTARY
LITERATURE
37
-
-
assay at
42
-
-
-
SOURCE TISSUE
ORGANISM
UNIPROT ACCESSION NO.
COMMENTARY
LITERATURE
SOURCE
MOLECULAR WEIGHT
MOLECULAR WEIGHT MAXIMUM
ORGANISM
UNIPROT ACCESSION NO.
COMMENTARY
LITERATURE
90000
-
A4IP64, A4ISB9
PAGE
117000
120000
-
PAGE, gel filtration
163000
-
-
gel filtration
380000
-
A4IP64, A4ISB9
PAGE
SUBUNITS
ORGANISM
UNIPROT ACCESSION NO.
COMMENTARY
LITERATURE
octamer
A4IP64, A4ISB9
8 * 45000, SDS-PAGE, 8 * 41664, calculated
octamer
-
8 * 45000, SDS-PAGE, 8 * 41664, calculated
-
tetramer
-
4 * 40000, SDS-PAGE
trimer
-
3 * 40000, SDS-PAGE
?
-
x * 35000, about, recombinant enzyme, SDS-PAGE
additional information
-
N-terminal sequence
additional information
-
secondary structure, unfolding by guanidine-HCl
additional information
-
N-terminal sequence
Crystallization/COMMENTARY
ORGANISM
UNIPROT ACCESSION NO.
LITERATURE
TEMPERATURE STABILITY
TEMPERATURE STABILITY MAXIMUM
ORGANISM
UNIPROT ACCESSION NO.
COMMENTARY
LITERATURE
50
-
-
stable up to
60
-
A4IP64, A4ISB9
14 h, more than 50% of initial activity; 14 h, more than 50% of initial activity
70
-
-
10 min, all activity lost
GENERAL STABILITY
ORGANISM
UNIPROT ACCESSION NO.
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
-
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 ACCESSION NO.
LITERATURE
recombinant His-tagged enzyme by nickel affinity chromatography
-
Cloned/COMMENTARY
ORGANISM
UNIPROT ACCESSION NO.
LITERATURE
expression in Escherichia coli; expression in Escherichia coli
A4IP64, A4ISB9
gene nosE, overexpression in Escherichia coli BL21(DE3) as N-terminally His-tagged enzyme
-