Information on EC 1.1.1.174 - cyclohexane-1,2-diol dehydrogenase

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The enzyme appears in viruses and cellular organisms

EC NUMBER
COMMENTARY hide
1.1.1.174
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RECOMMENDED NAME
GeneOntology No.
cyclohexane-1,2-diol dehydrogenase
REACTION
REACTION DIAGRAM
COMMENTARY hide
ORGANISM
UNIPROT
LITERATURE
trans-cyclohexane-1,2-diol + NAD+ = 2-hydroxycyclohexan-1-one + NADH + H+
show the reaction diagram
Also oxidizes, more slowly, the cis-isomer and 2-hydroxy-cyclohexanone
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REACTION TYPE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
oxidation
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-
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redox reaction
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-
-
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reduction
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-
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PATHWAY
BRENDA Link
KEGG Link
MetaCyc Link
Caprolactam degradation
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Microbial metabolism in diverse environments
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SYSTEMATIC NAME
IUBMB Comments
trans-cyclohexane-1,2-diol:NAD+ 1-oxidoreductase
Also oxidizes, more slowly, the cis isomer and 2-hydroxycyclohexanone.
CAS REGISTRY NUMBER
COMMENTARY hide
62628-27-7
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ORGANISM
COMMENTARY hide
LITERATURE
UNIPROT
SEQUENCE DB
SOURCE
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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
trans-cyclohexane-1,2-diol + NAD+
2-hydroxycyclohexan-1-one + NADH
show the reaction diagram
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metabolic pathway of trans-cyclohexan-1,2-diol to adipate
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r
trans-cyclohexane-1,2-diol + NAD+
2-hydroxycyclohexan-1-one + NADH + H+
show the reaction diagram
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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
trans-cyclohexane-1,2-diol + NAD+
2-hydroxycyclohexan-1-one + NADH
show the reaction diagram
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metabolic pathway of trans-cyclohexan-1,2-diol to adipate
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r
trans-cyclohexane-1,2-diol + NAD+
2-hydroxycyclohexan-1-one + NADH + H+
show the reaction diagram
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-
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-
?
COFACTOR
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
SPECIFIC ACTIVITY [µmol/min/mg]
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
0.85
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cell extracts, grown on trans-cyclohexan-1,2-diol
26.5
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partially purified
pH OPTIMUM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
7
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reduction of 2-hydroxycyclohexan-1-one
9.5 - 10
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oxidation of trans-cyclohexane-1,2-diol
SOURCE TISSUE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
SOURCE
Purification/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
Cloned/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
functional recombinant expression in Escherichia coli
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ENGINEERING
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
L181F
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random mutagenesis, A site mutant
L181F/I263N
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random mutagenesis, A site mutant
V78I/A82F/A328F/T438I
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random mutagenesis, B site mutant
V78I/A82I/A328N
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random mutagenesis, B site mutant
additional information
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whole-cell-catalyzed multiple regio- and stereoselective functionalizations in cascade reactions enabled by directed evolution: in Escherichia coli, expression of the recombinant enzyme leads to four different mutant whole cells, each leading to one of the three possible stereoisomeric forms of 1,2-cyclohexanediol, namely (R,R)-5, (S,S)-5, (S,R)-5 (meso), or (R,S)-5 (also meso), in a multi-step sequence, overview. Starting from the achiral substrates cyclohexane, cyclohexanol, or cyclohexanone, cyclohexane-1,2-diols as functionalized products are shown to be accessible in three different stereoisomeric forms