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Information on EC 1.1.1.245 - cyclohexanol dehydrogenase
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1.1.1.245 cyclohexanol dehydrogenaseIUBMB Comments
Also oxidizes some other alicyclic alcohols and diols.
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Word Map
- 1.1.1.245
- cyclohexanone
- monooxygenase
-
cycloalkanes
-
ncimb
- cyclopentanone
- acinetobacter
-
baeyer-villiger
-
alicyclic
- xanthobacter
- acidovorax
- lactones
- synthesis
The enzyme appears in viruses and cellular organisms
Synonyms
cyclohexanol dehydrogenase, 
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SYNONYM 
ORGANISM
UNIPROT
COMMENTARY 
LITERATURE
cyclohexanol dehydrogenase II
dehydrogenase, cyclohexanol
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-
-
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REACTION
REACTION DIAGRAM
COMMENTARY
ORGANISM
UNIPROT
LITERATURE
cyclohexanol + NAD+ = cyclohexanone + NADH + H+
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-
-
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REACTION TYPE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
oxidation
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-
redox reaction
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-
-
-
reduction
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-
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PATHWAY SOURCE
PATHWAYS
BRENDA
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SYSTEMATIC NAME
IUBMB Comments
cyclohexanol:NAD+ oxidoreductase
Also oxidizes some other alicyclic alcohols and diols.
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CAS REGISTRY NUMBER
COMMENTARY
63951-98-4
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SUBSTRATE
PRODUCT
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate)
(Substrate)
LITERATURE
(Substrate)
(Substrate)
COMMENTARY
(Product)
(Product)
LITERATURE
(Product)
(Product)
Reversibility
r=reversible
ir=irreversible
?=not specified
r=reversible
ir=irreversible
?=not specified
1,2-cycloheptanediol + NAD+
cycloheptane-1,2-dione + NADH
-
relative oxidation activity at 25% the rate of cyclohexanol oxidation
-
-
?
1-pentanol + NAD+
n-pentanal + NADH
-
relative activity at 23% the rate of cyclohexanol oxidation
-
-
?
2,3-butanediol + NAD+
? + NADH
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relative activity at 4% the rate of cyclohexanol oxidation
-
-
?
2,3-dimethylcyclohexanol + NAD+
2,3-dimethylcyclohexanone + NADH
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relative activity at 78% the rate of cyclohexanol oxidation
-
-
?
2,6-dimethylcyclohexanol + NAD+
2,6-dimethylcyclohexanone + NADH
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relative activity at 14% the rate of cyclohexanol oxidation
-
-
?
2-butanol + NAD+
2-butanone + NADH
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relative activity at 44% the rate of cyclohexanol oxidation
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-
?
2-cyclohexanol + NAD+
2-cyclohexenone + NADH
-
relative oxidation activity at 142% the rate of cyclohexanol oxidation
slow reduction
r
2-hydroxycyclohexanone + NADH
? + NAD+
-
relative activity at 50% the rate of cyclohexanone reduction
-
-
?
2-methyl-1-butanol + NAD+
2-methyl-1-butanal + NADH
-
relative activity at 26% the rate of cyclohexanol oxidation
-
-
?
2-methyl-1-propanol + NAD+
isobutyraldehyde + NADH
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relative activity at 17% the rate of cyclohexanol oxidation
-
-
?
2-methyl-2-propanol + NAD+
? + NADH
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relative activity at 16% the rate of cyclohexanol oxidation
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-
?
2-methylcyclohexanol + NAD+
2-methylcyclohexanone + NADH
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relative activity at 51% the rate of cyclohexanol oxidation
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-
?
2-pentanol + NAD+
2-pentanone + NADH
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relative activity at 43% the rate of cyclohexanol oxidation
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-
?
3-cyclohexyl-1-propanol + NAD+
3-cyclohexyl-1-propanal + NADH
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poor substrate
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-
?
3-hexanol + NAD+
3-hexanone + NADH
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relative activity at 196% the rate of cyclohexanol oxidation
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-
?
3-methylcyclohexanol + NAD+
3-methylcyclohexanone + NADH
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relative activity at 74% the rate of cyclohexanol oxidation
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-
?
4-heptanol + NAD+
4-heptanone + NADH
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relative activity at 125% the rate of cyclohexanol oxidation
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-
?
4-methylcyclohexanol + NAD+
4-methylcyclohexanone + NADH
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relative activity at 66% the rate of cyclohexanol oxidation
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-
?
cis-cyclopentane-1,2-diol + NAD+
? + NADH
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relative activity at 27% the rate of cyclohexanol oxidation
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-
?
cycloheptanone + NADH
cycloheptanol + NAD+
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relative activity at 10% the rate of cyclohexanone reduction
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?
cyclooctanol + NAD+
cyclooctanone + NADH
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relative activity at 500% the rate of cyclohexanol oxidation
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-
?
ethane-1,2-diol + NAD+
glyoxal + NADH
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relative activity at 5% the rate of cyclohexanol oxidation
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?
hexane-1,2-diol + NAD+
2-oxohexanal + NADH
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relative activity at 84% the rate of cyclohexanol oxidation
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-
?
hexane-1,6-diol + NAD+
hexanedial + NADH
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relative activity at 21% the rate of cyclohexanol oxidation
-
-
?
propane-1,2-diol + NAD+
methylglyoxal + NADH
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relative activity at 30% the rate of cyclohexanol oxidation
-
-
?
propane-1,3-diol + NAD+
? + NADH
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relative activity at 7% the rate of cyclohexanol oxidation
-
-
?
trans-cyclohexane-1,2-diol + NAD+
cyclohexane-1,2-dione + NADH + H+
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-
-
-
?
trans-cyclopentane-1,2-diol + NAD+
? + NADH
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relative activity at 114% the rate of cyclohexanol oxidation
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?
1-butanol + NAD+
butanal + NADH
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relative activity at 20% the rate of cyclohexanol oxidation
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?
1-heptanol + NAD+
heptanal + NADH
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relative oxidation activity at 32% the rate of cyclohexanol oxidation
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?
1-hexanol + NAD+
hexanal + NADH
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relative oxidation activity at 7% the rate of cyclohexanol oxidation
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?
1-hexanol + NAD+
hexanal + NADH
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relative oxidation activity at 21% the rate of cyclohexanol oxidation
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-
?
1-propanol + NAD+
propionaldehyde + NADH
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relative activity at 20% the rate of cyclohexanol oxidation
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?
2-propanol + NAD+
acetone + NADH
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relative activity at 19% the rate of cyclohexanol oxidation
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?
2-propanol + NAD+
acetone + NADH
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relative activity at 17% the rate of cyclohexanol oxidation
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?
cyclohexan-1,2-diol + NAD+
cyclohexane-1,2-dione + NADH
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relative oxidation activity at 43% the rate of cyclohexanol oxidation
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?
cyclohexan-1,2-diol + NAD+
cyclohexane-1,2-dione + NADH
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relative oxidation activity at 15% the rate of cyclohexanol oxidation
slow reduction
r
cyclohexan-1,2-diol + NAD+
cyclohexane-1,2-dione + NADH
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relative oxidation activity of cis-isomer at 28% the rate of cyclohexanol oxidation
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?
cyclohexan-1,2-diol + NAD+
cyclohexane-1,2-dione + NADH
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relative oxidation activity of cis/trans mixture at 123% the rate of cyclohexanol oxidation
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?
cyclohexan-1,2-diol + NAD+
cyclohexane-1,2-dione + NADH
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relative oxidation activity of trans-isomer at 146% the rate of cyclohexanol oxidation
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?
cyclohexan-1,2-diol + NAD+
cyclohexane-1,2-dione + NADH
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relative oxidation activity of cis-isomer at 28% the rate of cyclohexanol oxidation
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-
?
cyclohexane-1,3-diol + NAD+
cyclohexane-1,3-dione + NADH
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relative oxidation activity at 96% the rate of cyclohexanol oxidation
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?
cyclohexane-1,3-diol + NAD+
cyclohexane-1,3-dione + NADH
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relative oxidation activity at 14% the rate of cyclohexanol oxidation
slow reduction
r
cyclohexane-1,3-diol + NAD+
cyclohexane-1,3-dione + NADH
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relative oxidation activity at 28% the rate of cyclohexanol oxidation
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?
cyclohexane-1,4-diol + NAD+
cyclohexane-1,4-dione + NADH
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relative oxidation activity at 91% the rate of cyclohexanol oxidation
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-
?
cyclohexane-1,4-diol + NAD+
cyclohexane-1,4-dione + NADH
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relative oxidation activity at 36% the rate of cyclohexanol oxidation
relative reduction activity at 240% the rate of cyclohexanone reduction
r
cyclohexane-1,4-diol + NAD+
cyclohexane-1,4-dione + NADH
-
relative oxidation activity at 22% the rate of cyclohexanol oxidation
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?
cyclohexanol + NAD+
cyclohexanone + NADH
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metabolism of cyclohexane
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r
cyclohexanol + NAD+
cyclohexanone + NADH + H+
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temperature-induced conformational change is associated with the flexible loops directly involved in the substrate and coenzyme binding
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?
cyclopentanol + NAD+
cyclopentanone + NADH
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relative oxidation activity at 232% the rate of cyclohexanol oxidation
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?
cyclopentanol + NAD+
cyclopentanone + NADH
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relative reduction activity at 4% the rate of cyclohexanone reduction
r
cyclopentanol + NAD+
cyclopentanone + NADH
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relative oxidation activity at 77% the rate of cyclohexanol oxidation
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?
cyclopentanol + NAD+
cyclopentanone + NADH
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relative oxidation activity at 77% the rate of cyclohexanol oxidation
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?
ethanol + NAD+
acetaldehyde + NADH
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relative activity at 20% the rate of cyclohexanol oxidation
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?
ethanol + NAD+
acetaldehyde + NADH
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relative activity at 20% the rate of cyclohexanol oxidation
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?
methanol + NAD+
formaldehyde + NADH + H+
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relative activity at 2% the rate of cyclohexanol oxidation
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?
methanol + NAD+
formaldehyde + NADH + H+
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relative activity at 2% the rate of cyclohexanol oxidation
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?
additional information
additional information
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2-hydroxycyclohexanone, 1,3,5-trihydroxycyclohexane, menthol, ethanol, 1-propanol, 1-butanol and 1-pentanol are not oxidized with NAD+
2-cyclopentenone, 1,3-cyclohexanedione, 1,3-cyclopentanedione and 5-oxocapronate are not reduced with NADH
?
additional information
additional information
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cyclohexane-1,2-dione is not oxidized with NAD+
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-
?
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NATURAL SUBSTRATE
NATURAL PRODUCT
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate)
(Substrate)
LITERATURE
(Substrate)
(Substrate)
COMMENTARY
(Product)
(Product)
LITERATURE
(Product)
(Product)
REVERSIBILITY
r=reversible
ir=irreversible
?=not specified
r=reversible
ir=irreversible
?=not specified
cyclohexanol + NAD+
cyclohexanone + NADH
-
metabolism of cyclohexane
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r
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COFACTOR
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
NADH
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enzyme exhibits linearity of NAD(H) binding at pH 9.8 and at moderate ionic strength, in addition to positive cooperativity at pH 7.8 and 6.8, and at pH 9.8 in the presence of salt. NADH binding is positively cooperative below 20°C and negatively cooperative at 4050°. Steady-state kinetic measurements show that SsADH displays standard MichaelisMenten kinetics between 35°C and 45°C, but exhibits positive and negative cooperativity for NADH oxidation below and above this range of temperatures, respectively. Mutant N249Y displays non-cooperative behavious in coenzyme binding under the same experimental conditions used for the wild-type enzyme
NAD+
-
temperature-induced conformational change is associated with the flexible loops directly involved in the substrate and coenzyme binding
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METALS and IONS
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
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INHIBITOR
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
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KM VALUE [mM]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
additional information
additional information
-
steady-state kinetic measurements show that SsADH displays standard MichaelisMenten kinetics between 35°C and 45°C, but exhibits positive and negative cooperativity for NADH oxidation below and above this range of temperatures, respectively
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SPECIFIC ACTIVITY [µmol/min/mg]
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
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pH OPTIMUM
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
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TEMPERATURE RANGE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
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ORGANISM
COMMENTARY
LITERATURE
UNIPROT
SEQUENCE DB
SOURCE
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UNIPROT
ENTRY NAME
ORGANISM
NO. OF AA
NO. OF TRANSM. HELICES
MOLECULAR WEIGHT[Da]
SOURCE
SEQUENCE
LOCALIZATION PREDICTION
The reliability class of the localization prediction ranges from 1 (very reliable) to 5 (not reliable).
The reliability class of the localization prediction ranges from 1 (very reliable) to 5 (not reliable). A2R3W9_ASPNC
Aspergillus niger (strain CBS 513.88 / FGSC A1513)
262
0
27901
TrEMBL
other Location (Reliability: 2)
A2QLW6_ASPNC
Aspergillus niger (strain CBS 513.88 / FGSC A1513)
280
0
29523
TrEMBL
other Location (Reliability: 4)
A0A0H3C5H2_CAUVN
Caulobacter vibrioides (strain NA1000 / CB15N)
261
0
27011
TrEMBL
-
Q0K3M6_CUPNH
Cupriavidus necator (strain ATCC 17699 / DSM 428 / KCTC 22496 / NCIMB 10442 / H16 / Stanier 337)
261
0
27063
TrEMBL
-
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MOLECULAR WEIGHT
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
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SUBUNIT
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
dimer
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PROTEIN VARIANTS
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
N249Y
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mutant N249Y displays non-cooperative behavious in coenzyme binding under the same experimental conditions used for the wild-type enzyme (that exhibits linearity of NAD(H) binding at pH 9.8 and at moderate ionic strength, in addition to positive cooperativity at pH 7.8 and 6.8, and at pH 9.8 in the presence of salt. NADH binding is positively cooperative below 20°C and negatively cooperative at 4050°)
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pH STABILITY
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
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TEMPERATURE STABILITY
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
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STORAGE STABILITY
ORGANISM
UNIPROT
LITERATURE
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PURIFICATION (Commentary)
ORGANISM
UNIPROT
LITERATURE
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CLONED (Commentary)
ORGANISM
UNIPROT
LITERATURE
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APPLICATION
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
synthesis
synthesis of lactones from cycloalkanes. A heterologous pathway comprising enzymes with compatible kinetics is designed in Pseudomonas taiwanensis VLB120 enabling in-vivo cascade for synthesizing lactones from cycloalkanes. The respective pathway includes cytochrome P450 monooxygenase (CHX), cyclohexanol dehydrogenase (CDH), and cyclohexanone monooxygenase (CHXON) from Acidovorax sp. CHX100. Resting cells of the recombinant host Pseudomonas taiwanensis VLB120 convert cyclohexane, cyclohexanol, and cyclohexanone to epsilon-caprolactone at 22, 80-100, and 170 U/g cell dry weight, respectively. Cyclohexane (5 mM) is completely converted with a selectivity of 65% for epsilon-caprolactone formation in 2 h without accumulation of intermediate products
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REF.
AUTHORS
TITLE
JOURNAL
VOL.
PAGES
YEAR
ORGANISM (UNIPROT)
PUBMED ID
SOURCE
Dangel, W.; Tschech, A.; Fuchs, G.
Enzyme reactions involved in anaerobic cyclohexanol metabolism by a denitrifying Pseudomonas species
Arch. Microbiol.
152
273-279
1989
Pseudomonas sp.
-
brenda
Donoghue, N.A.; Trudgill, P.W.
The metabolism of cyclohexanol by Acinetobacter NCIB 9871
Eur. J. Biochem.
60
1-7
1975
Acinetobacter sp., Acinetobacter sp. NCIB 9871
brenda
Trower, M.K.; Buckland, R.M.; Higgins, R.; Griffin, M.
Isolation and characterization of a cyclohexane-metabolizing Xanthobacter sp.
Appl. Environ. Microbiol.
49
1282-1289
1985
Xanthobacter sp.
brenda
Stirling, L.A.; Perry, J.J.
Purification and properties of a nicotinamide adenine dinucleotide-linked cyclohexanol dehydrogenase from a Nocardia species
Curr. Microbiol.
4
37-40
1980
Nocardia sp.
-
brenda
Anderson M.A.; Hall, R.A.; Griffin, M.
Microbial metabolism of alicyclic hydrocarbons: cyclohexane catabolism by a pure strain of Pseudmonas sp.
J. Gen. Microbiol.
120
89-94
1980
Pseudomonas sp.
-
brenda
Tae-Kang, K.; Choi, J.H.; Rhee, I.K.
Purification and characterization of a cyclohexanol dehydrogenase from Rhodococcus sp. TK6
J. Microbiol. Biotechnol.
12
39-45
2002
Rhodococcus sp., Rhodococcus sp. TK6
-
brenda
Giordano, A.; Febbraio, F.; Russo, C.; Rossi, M.; Raia, C.A.
Evidence for co-operativity in coenzyme binding to tetrameric Sulfolobus solfataricus alcohol dehydrogenase and its structural basis: fluorescence, kinetic and structural studies of the wild-type enzyme and non-co-operative N249Y mutant
Biochem. J.
388
657-667
2005
Saccharolobus solfataricus
brenda
Secundo, F.; Russo, C.; Giordano, A.; Carrea, G.; Rossi, M.; Raia, C.A.
Temperature-induced conformational change at the catalytic site of Sulfolobus solfataricus alcohol dehydrogenase highlighted by Asn249Tyr substitution. A hydrogen/deuterium exchange, kinetic, and fluorescence quenching study
Biochemistry
44
11040-11048
2005
Saccharolobus solfataricus
brenda
Karande, R.; Salamanca, D.; Schmid, A.; Buehler, K.
Biocatalytic conversion of cycloalkanes to lactones using an in-vivo cascade in Pseudomonas taiwanensis VLB120
Biotechnol. Bioeng.
115
312-320
2017
Acidovorax sp. (A0A2D0WG37)
brenda
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