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trans-1,2-dihydrobenzene-1,2-diol + NADP+ = catechol + NADPH + H+
trans-1,2-dihydrobenzene-1,2-diol + NADP+ = catechol + NADPH + H+
overview about the regio- and stereospecificity for utilization of dihydrodiol derivatives as substrates
-
trans-1,2-dihydrobenzene-1,2-diol + NADP+ = catechol + NADPH + H+
isoform DD3 probably identical with 3(17)alpha-hydroxysteroid dehydrogenase EC 1.1.1.59 and D-xylose dehydrogenase EC 1.1.1.179
-
trans-1,2-dihydrobenzene-1,2-diol + NADP+ = catechol + NADPH + H+
structure analysis reveals that the enzyme belongs to the aldo-keto reductase superfamily, like 3alpha-hydroxysteroid dehydrogenase, 17beta-hydroxysteroid dehydrogenase, 20alpha-hydroxysteroid dehydrogenase, aldose reductase, and aldehyde reductase
-
trans-1,2-dihydrobenzene-1,2-diol + NADP+ = catechol + NADPH + H+
structure analysis reveals that the enzyme belongs to the aldo-keto reductase superfamily, like 3alpha-hydroxysteroid dehydrogenase, 17beta-hydroxysteroid dehydrogenase, 20alpha-hydroxysteroid dehydrogenase, aldose reductase, and aldehyde reductase
-
trans-1,2-dihydrobenzene-1,2-diol + NADP+ = catechol + NADPH + H+
enzyme termed 3alpha-hydroxysteroid/dihydrodiol dehydrogenase, structure-based catalytic mechanism analysis, ordered bi-bi mechanism
-
trans-1,2-dihydrobenzene-1,2-diol + NADP+ = catechol + NADPH + H+
cofactor binding and catalytic triad, alpha/beta-barrel structure
-
trans-1,2-dihydrobenzene-1,2-diol + NADP+ = catechol + NADPH + H+
enzyme is multifunctional: 3alpha-hydroxysteroid dehydrogenase activity, EC 1.1.1.50, dihydrodiol dehydrogenase activity, EC 1.3.1.20, and 9-, 11-, and15-hydroxyprostaglandin dehydrogenase activity, belongs to aldo-keto reductase superfamily
-
trans-1,2-dihydrobenzene-1,2-diol + NADP+ = catechol + NADPH + H+
D-xylose dehydrogenase EC 1.1.1.179 and dihydrodiol dehydrogenase EC 1.3.1.20 both follow an ordered bi-bi mechanism and are thus considered the same enzyme
-
trans-1,2-dihydrobenzene-1,2-diol + NADP+ = catechol + NADPH + H+
identical with D-xylose dehydrogenase EC 1.1.1.179
-
trans-1,2-dihydrobenzene-1,2-diol + NADP+ = catechol + NADPH + H+
probably identical with aldehyde reductase EC 1.1.1.2
-
trans-1,2-dihydrobenzene-1,2-diol + NADP+ = catechol + NADPH + H+
probably identical with D-xylose dehydrogenase EC 1.1.1.179
-
trans-1,2-dihydrobenzene-1,2-diol + NADP+ = catechol + NADPH + H+
isoforms belong to aldo-keto reductase superfamily
trans-1,2-dihydrobenzene-1,2-diol + NADP+ = catechol + NADPH + H+
termed AKR1C as member of the aldo-keto-superfamily, overview
-
trans-1,2-dihydrobenzene-1,2-diol + NADP+ = catechol + NADPH + H+
the cytosolic, but not the microsomal, enzyme is identical with 3alpha-hydroxysteroid dehydrogenase EC 1.1.1.50
-
trans-1,2-dihydrobenzene-1,2-diol + NADP+ = catechol + NADPH + H+
DD4 is identical with human chlordecone reductase and 3alpha-hydroxysteroid dehydrogenase type 1, EC 1.1.1.213, catalyzes the oxidoreduction of various 3alpha-hydroxysteroids including bile acids and belong to the aldo-keto reductase superfamily, in this concern termed AKR1C4
-
trans-1,2-dihydrobenzene-1,2-diol + NADP+ = catechol + NADPH + H+
isoform DD1 is identical with 3alpha-hydroxysteroid dehydrogenase EC 1.1.1.50, while isoform DD3 is a unique benzene dihydrodiol-specific enzyme
-
trans-1,2-dihydrobenzene-1,2-diol + NADP+ = catechol + NADPH + H+
-
-
-
-
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(R)-tetralol + NADP+
? + NADPH
(S)-(+)-1,2,3,4-tetrahydronaphth-1-ol + NADP+
? + NADPH
(S)-indan-1-ol + NADP+
? + NADPH
(S)-tetralol + NADP+
? + NADPH
1-acenaphthenol + NAD(P)+
?
1-acenaphthol + NADP+
acenaphthylen-1-ol + NADPH
-
-
-
-
?
1-indanol + NADP+
3H-inden-1-ol + NADPH
17beta-estradiol + NAD(P)+
?
2,3-heptanedione + NADPH
?
-
-
-
-
?
2,3-hexanedione + NADPH
?
2,3-pentanedione + NADPH
?
2-cyclohexen-1-ol + NADP+
2-cyclohexene-1-one + NADPH
-
NAD+
-
-
?
2-deoxy-D-glucose + NADP+
2-deoxy-D-glucono-1,5-lactone + NADPH + H+
3-deoxyglucosone + NADPH
?
-
-
-
-
?
3-keto steroid + NAD(P)H
3alpha-hydroxy steroid + NAD(P)+
3-nitrobenzaldehyde + NADPH
3-nitrobenzylalcohol + NADP+
-
-
-
-
?
3alpha-hydroxy steroid + NADP+
3-keto steroid + NADPH
4-carboxybenzaldehyde + NADPH
?
-
-
-
-
?
4-chromanol + NADP+
?
-
-
-
r
4-chromanol + NADP+
? + NADPH
4-nitrobenzaldehyde + NAD(P)H
4-nitrobenzylalcohol + NAD(P)+
5alpha-androstan-3,17-dione + NADPH
5alpha-androstan-3alpha-ol-17-one + NADP+
-
isoform DD1, identical with 3alpha-hydroxysteroid dehydrogenase EC 1.1.1.50
-
-
?
5alpha-dihydrotestosterone + NADPH + H+
5alpha-androstan-3alpha,17beta-diol + NADP+
5beta-androstan-3,17-dione + NADPH
5beta-androstan-3alpha-ol-17-one + NADP+
5beta-androstan-3alpha,17beta-diol + NADP+
5beta-androstan-3,17-dione + NADPH
5beta-dihydrocortisone + NADPH
?
-
-
-
-
?
5beta-pregnan-3,20-diol + NADP+
5beta-pregnan-20-ol-3-one + NADPH
5beta-pregnan-3,20-dione + NADPH
3alpha-hydroxy-5beta-pregnan-20-one + NADP+
-
-
-
-
?
7alpha-hydroxy-5beta-cholestan-3-one + NADPH
?
-
-
-
-
?
acenaphthenequinone + NADPH
?
-
-
-
-
?
acetoin + NADP+
?
-
-
-
-
?
alicyclic alcohol + NAD(P)+
?
camphorquinone + NAD(P)H
(1R)-1,7,7-trimethylbicyclo[2.2.1]heptane-2,3-diol + NADP+
camphorquinone + NADPH
?
-
-
-
-
?
camphorquinone + NADPH + H+
?
enzyme has dehydrogenase and reductase activities, enzyme is identical to NADP+-dependent D-xylose dehydrogenase
-
-
?
chenodeoxycholic acid + NADP+
?
-
DD1
-
-
?
cis-1,2-dihydrobenzene-1,2-diol + NAD(P)+
catechol + NAD(P)H
D-arabinose + NADP+
D-arabinono-1,4-lactone + NADPH
D-galactose + NADP+
D-galactono-1,5-lactone + NADPH
D-glucose + NADP+
D-glucono-1,5-lactone + NADPH + H+
D-glucuronate + NADP+
D-glucurono-1,5-lactone + NADPH
-
isoform DD4 no activity
-
-
r
D-glyceraldehyde + NADPH
?
D-lactaldehyde + NADP+
?
-
-
-
-
?
D-xylose + NADP+
D-xylono-1,5-lactone + NADPH + H+
deoxycholic acid + NADP+
?
-
DD1
-
-
?
dihydroxyacetone + NADPH
?
dihydroxyacetone phosphate + NADPH
?
-
-
-
-
?
DL-glyceraldehyde + NADPH
?
-
probable identity with aldehyde reductase EC 1.1.1.2
-
-
?
DL-glyceraldehyde-3-phosphate + NADPH
?
-
-
-
-
?
epitestosterone + NAD(P)+
?
-
isoform DD3: dihydrodiol dehydrogenase EC 1.3.1.20 and 3(17)alpha-hydroxysteroid dehydrogenase EC 1.1.1.59 activities reside on a single protein
-
-
?
ethyl pyruvate + NADPH
ethyl lactate + NADP+
-
-
-
-
?
glycolithocholic acid + NAD(P)+
3-oxo-glycocholanoic acid + NAD(P)H
-
NAD+ preferred as cofactor
-
-
?
L-glyceraldehyde + NADPH
?
L-lactaldehyde + NADP+
?
-
-
-
-
?
lithocholic acid + NADP+
?
methyl pyruvate + NADPH
methyl lactate + NADP+
-
-
-
-
?
methylglyoxal + NADPH
?
-
-
-
-
?
naphthalene dihydrodiol + NAD(P)+
?
naphthalene dihydrodiol + NADP+
? + NADPH + H+
-
-
-
-
?
phenyl-1,2-propanedione + NADPH
?
-
-
-
-
?
phenylglyoxal + NADPH
?
-
-
-
-
?
pyridine-3-aldehyde + NADPH
?
pyridine-4-aldehyde + NADPH
?
-
-
-
-
?
S-(+)-1,2,3,4-tetrahydronaphth-1-ol + NADP+
? + NADPH
succinic semialdehyde + NADPH
?
-
isoform DD4 low activity
-
-
?
taurochenodeoxycholic acid + NADP+
?
-
DD1, DD3
-
-
?
taurocholic acid + NADP+
?
-
DD1
-
-
?
taurolithocholic acid + NADP+
?
-
DD1, DD3
-
-
?
testosterone + NADPH + H+
4-androsten-3alpha,17beta-diol + NADP+
-
NAD+
-
-
?
tetrahydrodeoxycorticosterone + NAD(P)+
?
-
isoform DD3: dihydrodiol dehydrogenase EC 1.3.1.20 and 3(17)alpha-hydroxysteroid dehydrogenase EC 1.1.1.59 activities reside on a single protein
-
-
?
trans-1,2-dihydrobenzene-1,2-diol + NAD(P)+
catechol + NAD(P)H
trans-1,2-dihydroxy-1,2-dihydrophenanthrene + NADPH
?
-
-
-
-
?
trans-7,8-dihydroxy-7,8-dihydrobenzo[a]pyrene + NADP+
benzo[a]-pyrene-7,8-dione + NADPH
DD1, DD2, DD4, 3alpha-hydroxysteroid/dihydrodiol dehydrogenase
product is potent carcinogen
?
trans-benzene dihydrodiol + NADP+
? + NADPH
trans-naphthalene dihydrodiol + NAD(P)+
?
[1R,2R]-trans-cyclohexanediol + NADP+
?
-
-
-
-
?
additional information
?
-
(R)-indan-1-ol + NADP+
?
-
-
-
-
?
(R)-indan-1-ol + NADP+
?
-
DD4, recombinant double mutant S145C/L311V
-
-
?
(R)-tetralol + NADP+
?
-
DD4, recombinant double mutant S145C/L311V
-
-
?
(R)-tetralol + NADP+
?
-
-
-
?
(R)-tetralol + NADP+
? + NADPH
dehydrogenase activity
-
-
r
(R)-tetralol + NADP+
? + NADPH
dehydrogenase activity
-
-
r
(S)-(+)-1,2,3,4-tetrahydronaphth-1-ol + NADP+
? + NADPH
-
-
-
?
(S)-(+)-1,2,3,4-tetrahydronaphth-1-ol + NADP+
? + NADPH
dehydrogenase activity
-
-
r
(S)-indan-1-ol + NADP+
?
-
DD3
-
-
?
(S)-indan-1-ol + NADP+
?
-
-
-
-
?
(S)-indan-1-ol + NADP+
?
-
-
-
?
(S)-indan-1-ol + NADP+
?
-
DD4, wild-type and recombinant double mutant S145C/L311V
-
-
?
(S)-indan-1-ol + NADP+
?
-
DD1, DD4, mutant CDD1-4, mutant CDD4-1
-
-
?
(S)-indan-1-ol + NADP+
?
recombinant DD1, DD1, DD2
-
-
?
(S)-indan-1-ol + NADP+
?
-
-
-
?
(S)-indan-1-ol + NADP+
? + NADPH
dehydrogenase activity
-
-
r
(S)-indan-1-ol + NADP+
? + NADPH
dehydrogenase activity
-
-
r
(S)-tetralol + NADP+
?
DD1, DD2, recombinant DD1
-
-
?
(S)-tetralol + NADP+
?
-
DD4, recombinant double mutant S145C/L311V
-
-
?
(S)-tetralol + NADP+
?
-
-
-
?
(S)-tetralol + NADP+
? + NADPH
dehydrogenase activity
-
-
r
(S)-tetralol + NADP+
? + NADPH
dehydrogenase activity
-
-
r
1-acenaphthenol + NAD(P)+
?
-
-
-
-
?
1-acenaphthenol + NAD(P)+
?
-
DD3
-
-
?
1-acenaphthenol + NAD(P)+
?
recombinant: DD1, DD2, and 3alpha-hydroysteroid dehydrogenase/dihydrodiol dehydrogenase
-
-
?
1-acenaphthenol + NAD(P)+
?
-
-
-
-
?
1-indanol + NADP+
3H-inden-1-ol + NADPH
-
-
-
-
?
1-indanol + NADP+
3H-inden-1-ol + NADPH
-
-
-
?
17beta-estradiol + NAD(P)+
?
-
-
-
-
?
17beta-estradiol + NAD(P)+
?
-
isoform DD3: dihydrodiol dehydrogenase EC 1.3.1.20 and 3(17)alpha-hydroxysteroid dehydrogenase EC 1.1.1.59 activities reside on a single protein
-
-
?
2,3-hexanedione + NADPH
?
-
-
-
-
?
2,3-hexanedione + NADPH
?
-
-
-
-
?
2,3-pentanedione + NADPH
?
-
-
-
-
?
2,3-pentanedione + NADPH
?
-
-
-
-
?
2-deoxy-D-glucose + NADP+
2-deoxy-D-glucono-1,5-lactone + NADPH + H+
-
low activity
-
-
?
2-deoxy-D-glucose + NADP+
2-deoxy-D-glucono-1,5-lactone + NADPH + H+
-
low activity
-
-
?
2-deoxy-D-glucose + NADP+
2-deoxy-D-glucono-1,5-lactone + NADPH + H+
-
low activity
-
-
?
2-deoxy-D-glucose + NADP+
2-deoxy-D-glucono-1,5-lactone + NADPH + H+
-
low activity
-
-
?
3-keto steroid + NAD(P)H
3alpha-hydroxy steroid + NAD(P)+
-
probably reversible reaction
-
-
?
3-keto steroid + NAD(P)H
3alpha-hydroxy steroid + NAD(P)+
-
-
-
r
3-keto steroid + NAD(P)H
3alpha-hydroxy steroid + NAD(P)+
-
reduces biologically important 3-oxo steroids of the androstane, pregnane, and cholane series
-
-
?
3alpha-hydroxy steroid + NADP+
3-keto steroid + NADPH
-
not, DD3
-
-
?
3alpha-hydroxy steroid + NADP+
3-keto steroid + NADPH
-
-
-
-
?
3alpha-hydroxy steroid + NADP+
3-keto steroid + NADPH
-
-
-
-
?
3alpha-hydroxy steroid + NADP+
3-keto steroid + NADPH
-
-
-
-
?
3alpha-hydroxy steroid + NADP+
3-keto steroid + NADPH
-
-
-
-
?
4-chromanol + NADP+
? + NADPH
dehydrogenase activity
-
-
r
4-chromanol + NADP+
? + NADPH
dehydrogenase activity
-
-
r
4-nitrobenzaldehyde + NAD(P)H
4-nitrobenzylalcohol + NAD(P)+
-
-
-
-
?
4-nitrobenzaldehyde + NAD(P)H
4-nitrobenzylalcohol + NAD(P)+
-
DD2, DD3
-
-
?
4-nitrobenzaldehyde + NAD(P)H
4-nitrobenzylalcohol + NAD(P)+
-
-
-
-
?
4-nitrobenzaldehyde + NAD(P)H
4-nitrobenzylalcohol + NAD(P)+
-
-
-
-
?
5alpha-dihydrotestosterone + NADPH + H+
5alpha-androstan-3alpha,17beta-diol + NADP+
-
-
-
-
?
5alpha-dihydrotestosterone + NADPH + H+
5alpha-androstan-3alpha,17beta-diol + NADP+
-
-
-
r
5beta-androstan-3,17-dione + NADPH
5beta-androstan-3alpha-ol-17-one + NADP+
-
-
-
-
?
5beta-androstan-3,17-dione + NADPH
5beta-androstan-3alpha-ol-17-one + NADP+
-
-
-
-
?
5beta-androstan-3alpha,17beta-diol + NADP+
5beta-androstan-3,17-dione + NADPH
-
-
-
-
?
5beta-androstan-3alpha,17beta-diol + NADP+
5beta-androstan-3,17-dione + NADPH
DD1, DD2, recombinant DD1
-
-
?
5beta-androstan-3alpha,17beta-diol + NADP+
5beta-androstan-3,17-dione + NADPH
-
DD4 wild-type and mutants
-
-
?
5beta-pregnan-3,20-diol + NADP+
5beta-pregnan-20-ol-3-one + NADPH
-
-
-
-
?
5beta-pregnan-3,20-diol + NADP+
5beta-pregnan-20-ol-3-one + NADPH
DD1, DD2, recombinant DD1
-
-
?
alicyclic alcohol + NAD(P)+
?
-
not:
-
-
?
alicyclic alcohol + NAD(P)+
?
-
-
-
-
?
androsterone + NADPH
?
-
DD1, identical with 3alpha-hydroxysteroid dehydrogenase EC 1.1.1.50
-
-
?
androsterone + NADPH
?
-
-
-
-
?
androsterone + NADPH
?
-
DD4 wild-type and mutants
-
-
?
androsterone + NADPH
?
recombinant DD4
-
-
?
camphorquinone + NAD(P)H
(1R)-1,7,7-trimethylbicyclo[2.2.1]heptane-2,3-diol + NADP+
-
-
-
-
?
camphorquinone + NAD(P)H
(1R)-1,7,7-trimethylbicyclo[2.2.1]heptane-2,3-diol + NADP+
-
-
-
?
camphorquinone + NAD(P)H
(1R)-1,7,7-trimethylbicyclo[2.2.1]heptane-2,3-diol + NADP+
-
-
-
-
?
camphorquinone + NAD(P)H
(1R)-1,7,7-trimethylbicyclo[2.2.1]heptane-2,3-diol + NADP+
-
-
-
-
?
camphorquinone + NAD(P)H
(1R)-1,7,7-trimethylbicyclo[2.2.1]heptane-2,3-diol + NADP+
-
-
-
-
?
camphorquinone + NAD(P)H
(1R)-1,7,7-trimethylbicyclo[2.2.1]heptane-2,3-diol + NADP+
-
-
-
-
?
camphorquinone + NAD(P)H
(1R)-1,7,7-trimethylbicyclo[2.2.1]heptane-2,3-diol + NADP+
-
-
-
?
camphorquinone + NAD(P)H
(1R)-1,7,7-trimethylbicyclo[2.2.1]heptane-2,3-diol + NADP+
-
-
-
?
camphorquinone + NAD(P)H
(1R)-1,7,7-trimethylbicyclo[2.2.1]heptane-2,3-diol + NADP+
-
-
-
-
?
cholic acid + NADP+
?
-
DD1
-
-
?
cholic acid + NADP+
?
-
-
-
-
?
cholic acid + NADP+
?
-
DD4, wild-type and recombinant double mutant S145C/L311V
-
-
?
cis-1,2-dihydrobenzene-1,2-diol + NAD(P)+
catechol + NAD(P)H
-
not:
-
-
?
cis-1,2-dihydrobenzene-1,2-diol + NAD(P)+
catechol + NAD(P)H
-
not:
-
-
?
cis-1,2-dihydrobenzene-1,2-diol + NAD(P)+
catechol + NAD(P)H
-
-
-
-
r
D-arabinose + NADP+
D-arabinono-1,4-lactone + NADPH
-
low activity
-
-
?
D-arabinose + NADP+
D-arabinono-1,4-lactone + NADPH
-
low activity
-
-
?
D-arabinose + NADP+
D-arabinono-1,4-lactone + NADPH
-
low activity
-
-
?
D-arabinose + NADP+
D-arabinono-1,4-lactone + NADPH
-
low activity
-
-
?
D-galactose + NADP+
D-galactono-1,5-lactone + NADPH
-
low activity
-
-
?
D-galactose + NADP+
D-galactono-1,5-lactone + NADPH
-
only isoform DD3
-
-
?
D-galactose + NADP+
D-galactono-1,5-lactone + NADPH
-
low activity
-
-
?
D-galactose + NADP+
D-galactono-1,5-lactone + NADPH
-
low activity
-
-
?
D-galactose + NADP+
D-galactono-1,5-lactone + NADPH
-
low activity
-
-
?
D-glucose + NADP+
D-glucono-1,5-lactone + NADPH + H+
-
low activity
-
-
?
D-glucose + NADP+
D-glucono-1,5-lactone + NADPH + H+
-
only isoform DD3
-
-
?
D-glucose + NADP+
D-glucono-1,5-lactone + NADPH + H+
-
low activity
-
-
?
D-glucose + NADP+
D-glucono-1,5-lactone + NADPH + H+
-
low activity
-
-
?
D-glucose + NADP+
D-glucono-1,5-lactone + NADPH + H+
-
low activity
-
-
?
D-glyceraldehyde + NADPH
?
-
-
-
-
?
D-glyceraldehyde + NADPH
?
-
DD2 and DD3 show high activity, DD4 only shows low activity
-
-
?
D-glyceraldehyde + NADPH
?
-
-
-
-
?
D-ribose + NADP+
?
-
-
-
-
?
D-ribose + NADP+
?
-
-
-
-
?
D-ribose + NADP+
?
-
-
-
-
?
D-ribose + NADP+
?
-
-
-
-
?
D-xylose + NADP+
D-xylono-1,5-lactone + NADPH + H+
-
-
-
?
D-xylose + NADP+
D-xylono-1,5-lactone + NADPH + H+
-
also low activity with L-xylose
-
-
?
D-xylose + NADP+
D-xylono-1,5-lactone + NADPH + H+
-
-
-
-
1.3.1.20 trans-1,2-dihydrobenzene-1,2-diol dehydrogenase
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