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Literature summary for 1.3.1.20 extracted from

  • Carbone, V.; Sumii, R.; Ishikura, S.; Asada, Y.; Hara, A.; El-Kabbani, O.
    Structure of monkey dimeric dihydrodiol dehydrogenase in complex with isoascorbic acid (2008), Acta Crystallogr. Sect. D, 64, 532-542.
    View publication on PubMed
Search for more literature for 1.3.1.20

Cloned(Commentary)

Cloned (Comment) Organism
expressed in Escherichia coli BL21 (DE3) cells Macaca fuscata
wild-type protein and mutants are expressed in Escherichia coli BL21 (DE3) Macaca fascicularis

Crystallization (Commentary)

Crystallization (Comment) Organism
crystals are obtained at 19.9°C in a culture plate via the vapour-diffusion method, crystal structure of dimeric dihydrodiol dehydrogenase complexed with the inhibitor isoascorbic acid is determined at 2.59 A resolution Macaca fascicularis
in complex with isoascorbic acid, vapour diffusion method with 2 M ammonium sulfate, 0.1 M sodium citrate buffer pH 5.0, at 20°C Macaca fuscata

Protein Variants

Protein Variants Comment Organism
A36D shows a decreased kcat value compared to the wild type enzyme Macaca fuscata
A36D production by site-directed mutagenesis Macaca fascicularis
D280A shows a decreased kcat value compared to the wild type enzyme Macaca fuscata
D280A production by site-directed mutagenesis Macaca fascicularis
F154A shows a decreased kcat value compared to the wild type enzyme Macaca fuscata
F154A production by site-directed mutagenesis Macaca fascicularis
F279A shows a decreased kcat value compared to the wild type enzyme Macaca fuscata
F279A production by site-directed mutagenesis Macaca fascicularis
H76Q shows a decreased kcat value compared to the wild type enzyme Macaca fuscata
H76Q production by site-directed mutagenesis Macaca fascicularis
H79Q shows a decreased kcat value compared to the wild type enzyme Macaca fuscata
H79Q production by site-directed mutagenesis Macaca fascicularis
K97M shows a decreased kcat value compared to the wild type enzyme Macaca fuscata
K97M production by site-directed mutagenesis Macaca fascicularis
K97R shows a decreased kcat value compared to the wild type enzyme Macaca fuscata
K97R production by site-directed mutagenesis Macaca fascicularis
R37A shows a decreased kcat value compared to the wild type enzyme Macaca fuscata
R37A production by site-directed mutagenesis Macaca fascicularis
R37D shows a decreased kcat value compared to the wild type enzyme Macaca fuscata
R37D production by site-directed mutagenesis Macaca fascicularis
R41A shows a decreased kcat value compared to the wild type enzyme Macaca fuscata
R41A production by site-directed mutagenesis Macaca fascicularis
R41D shows a decreased kcat value compared to the wild type enzyme Macaca fuscata
R41D production by site-directed mutagenesis Macaca fascicularis
W125Y shows a decreased kcat value compared to the wild type enzyme Macaca fuscata
W125Y production by site-directed mutagenesis Macaca fascicularis
W254A shows a decreased kcat value compared to the wild type enzyme Macaca fuscata
W254A production by site-directed mutagenesis Macaca fascicularis
W254Y shows a decreased kcat value compared to the wild type enzyme Macaca fuscata
W254Y production by site-directed mutagenesis Macaca fascicularis

Inhibitors

Inhibitors Comment Organism Structure
4-hydroxyacetophenone
-
 Macaca fascicularis
4-hydroxyacetophenone
-
 Macaca fuscata
isoascorbic acid competitive inhibitor Macaca fascicularis
isoascorbic acid
-
 Macaca fuscata

KM Value [mM]

KM Value [mM] KM Value Maximum [mM] Substrate Comment Organism Structure
0.1
-
 Camphorquinone wild type enzyme, in 25 mM Tris-HCl pH 7.5, at 25°C Macaca fuscata
0.84
-
 Camphorquinone mutant enzyme W254Y, in 25 mM Tris-HCl pH 7.5, at 25°C Macaca fuscata
0.84
-
 Camphorquinone reduction reaction of mutant W254Y, using 0.1 mM NADPH as coenzyme Macaca fascicularis
1.5
-
 Camphorquinone mutant enzyme F154A, in 25 mM Tris-HCl pH 7.5, at 25°C Macaca fuscata
1.5
-
 Camphorquinone reduction reaction of mutant F154A, using 0.1 mM NADPH as coenzyme Macaca fascicularis
2.4
-
 Camphorquinone reduction reaction of mutant R41D, using 0.1 mM NADPH as coenzyme Macaca fascicularis
2.6
-
 Camphorquinone reduction reaction of mutant F279A, using 0.1 mM NADPH as coenzyme Macaca fascicularis
3.1
-
 Camphorquinone reduction reaction of mutant R37D, using 0.1 mM NADPH as coenzyme Macaca fascicularis
3.6
-
 Camphorquinone mutant enzyme W254A, in 25 mM Tris-HCl pH 7.5, at 25°C Macaca fuscata
3.6
-
 Camphorquinone reduction reaction of mutant W254A, using 0.1 mM NADPH as coenzyme Macaca fascicularis
4.4
-
 D-xylose wild type enzyme, in 25 mM Tris-HCl pH 7.5, at 25°C Macaca fuscata
5.1
-
 Camphorquinone reduction reaction of mutant H76Q, using 0.1 mM NADPH as coenzyme Macaca fascicularis
5.2
-
 Camphorquinone reduction reaction of mutant R37A, using 0.1 mM NADPH as coenzyme Macaca fascicularis
8.1
-
 Camphorquinone reduction reaction of mutant A36D, using 0.1 mM NADPH as coenzyme Macaca fascicularis
11
-
 Camphorquinone reduction reaction of wild type enzyme, using 0.1 mM NADPH as coenzyme Macaca fascicularis
12
-
 Camphorquinone reduction reaction of mutant H79Q, using 0.1 mM NADPH as coenzyme Macaca fascicularis
13
-
 Camphorquinone mutant enzyme W125Y, in 25 mM Tris-HCl pH 7.5, at 25°C Macaca fuscata
13
-
 Camphorquinone reduction reaction of mutant W125Y, using 0.1 mM NADPH as coenzyme Macaca fascicularis
14
-
 D-xylose mutant enzyme W254Y, in 25 mM Tris-HCl pH 7.5, at 25°C Macaca fuscata
17
-
 Camphorquinone reduction reaction of mutant K97M, using 0.1 mM NADPH as coenzyme Macaca fascicularis
20
-
 D-xylose mutant enzyme F279A, in 25 mM Tris-HCl pH 7.5, at 25°C Macaca fuscata
21
-
 Camphorquinone reduction reaction of mutant K79R, using 0.1 mM NADPH as coenzyme Macaca fascicularis
26
-
 Camphorquinone mutant enzyme F279A, in 25 mM Tris-HCl pH 7.5, at 25°C Macaca fuscata
36
-
 D-xylose mutant enzyme F154A, in 25 mM Tris-HCl pH 7.5, at 25°C Macaca fuscata
67
-
 D-xylose mutant enzyme W125Y, in 25 mM Tris-HCl pH 7.5, at 25°C Macaca fuscata
90
-
 D-xylose mutant enzyme W254A, in 25 mM Tris-HCl pH 7.5, at 25°C Macaca fuscata

Natural Substrates/ Products (Substrates)

Natural Substrates Organism Comment (Nat. Sub.) Natural Products Comment (Nat. Pro.) Rev. Reac.
camphorquinone + NADPH + H+ Macaca fascicularis enzyme has dehydrogenase and reductase activities, enzyme is identical to NADP+-dependent D-xylose dehydrogenase ?
-
 ?
additional information Macaca fascicularis dihydrodiol dehydrogenase catalyzes the NADP+-linked oxidation of dihydrodiols of aromatic hydrocarbons to their corresponding catechols and is regarded as a toxication enzyme in the metabolism of carcinogenic polycyclic aromatic hydrocarbons because oxidation by the enzyme yields reactive and redox-active ortho-quinones and reactive oxygen species, broad substrate specificity indicates additional roles of the enzyme in the metabolism of endogenous and xenobiotic carbonyl compounds and the prevention of the development of glycation ?
-
 ?

Organism

Organism UniProt Comment Textmining
Macaca fascicularis Q9TQS6
-
-
Macaca fuscata
-
-
-

Purification (Commentary)

Purification (Comment) Organism
-
 Macaca fuscata
the recombinant enzymes are purified from the 12000g supernatants of the homogenates of the cells Macaca fascicularis

Substrates and Products (Substrate)

Substrates Comment Substrates Organism Products Comment (Products) Rev. Reac.
camphorquinone + NAD(P)H
-
 Macaca fuscata (1R)-1,7,7-trimethylbicyclo[2.2.1]heptane-2,3-diol + NADP+
-
 ?
camphorquinone + NADPH + H+ enzyme has dehydrogenase and reductase activities, enzyme is identical to NADP+-dependent D-xylose dehydrogenase Macaca fascicularis ?
-
 ?
D-xylose + NADP+
-
 Macaca fuscata D-xylono-1,5-lactone + NADPH + H+
-
 ?
additional information dihydrodiol dehydrogenase catalyzes the NADP+-linked oxidation of dihydrodiols of aromatic hydrocarbons to their corresponding catechols and is regarded as a toxication enzyme in the metabolism of carcinogenic polycyclic aromatic hydrocarbons because oxidation by the enzyme yields reactive and redox-active ortho-quinones and reactive oxygen species, broad substrate specificity indicates additional roles of the enzyme in the metabolism of endogenous and xenobiotic carbonyl compounds and the prevention of the development of glycation Macaca fascicularis ?
-
 ?

Subunits

Subunits Comment Organism
dimer
-
 Macaca fascicularis
dimer x-ray crystallography Macaca fuscata

Synonyms

Synonyms Comment Organism
dihydrodiol dehydrogenase
-
 Macaca fuscata
dihydrodiol dehydrogenase
-
 Macaca fascicularis

Turnover Number [1/s]

Turnover Number Minimum [1/s] Turnover Number Maximum [1/s] Substrate Comment Organism Structure
0.004
-
 Camphorquinone reduction reaction of mutant K79R, 0.1 mM NADPH Macaca fascicularis
0.004
-
 Camphorquinone reduction reaction of mutant K97M, 0.1 mM NADPH Macaca fascicularis
0.02
-
 Camphorquinone reduction oxidation reaction of mutant A36D, 0.1 mM NADPH Macaca fascicularis
0.05
-
 Camphorquinone reduction oxidation reaction of mutante R37D, 0.1 mM NADPH Macaca fascicularis
0.6
-
 Camphorquinone reduction reaction of mutant H79Q, 0.1 mM NADPH Macaca fascicularis
0.9
-
 Camphorquinone oxidation reaction of mutant R41D, 0.1 mM NADPH Macaca fascicularis
2.1
-
 Camphorquinone reduction reaction of mutant R37A, 0.1 mM NADPH Macaca fascicularis
2.6
-
 D-xylose wild type enzyme, in 25 mM Tris-HCl pH 7.5, at 25°C Macaca fuscata
3.6
-
 Camphorquinone reduction reaction of mutant H76Q, 0.1 mM NADPH Macaca fascicularis
20
-
 Camphorquinone wild type enzyme, in 25 mM Tris-HCl pH 7.5, at 25°C Macaca fuscata
20
-
 Camphorquinone reduction reaction of wild type enzyme, 0.1 mM NADPH Macaca fascicularis

Cofactor

Cofactor Comment Organism Structure
NAD(P)H high affinity for NADP(H) Macaca fuscata
NADP+
-
 Macaca fascicularis
NADPH
-
 Macaca fascicularis

IC50 Value

IC50 Value IC50 Value Maximum Comment Organism Inhibitor Structure
0.00097
-
 wild type enzyme, in 25 mM Tris-HCl pH 7.5, at 25°C Macaca fuscata 4-hydroxyacetophenone
0.00097
-
 determined in the camphorquinone reduction, inhibitor is uncompetitive with respect to camphorquinone Macaca fascicularis 4-hydroxyacetophenone
0.006
-
 mutant enzyme W254Y, in 25 mM Tris-HCl pH 7.5, at 25°C Macaca fuscata 4-hydroxyacetophenone
0.006
-
 mutant W254Y Macaca fascicularis 4-hydroxyacetophenone
0.037
-
 wild type enzyme, in 25 mM Tris-HCl pH 7.5, at 25°C Macaca fuscata isoascorbic acid
0.038
-
 mutant enzyme W254Y, in 25 mM Tris-HCl pH 7.5, at 25°C Macaca fuscata isoascorbic acid
0.038
-
 determined in the camphorquinone reduction, inhibitor is uncompetitive with respect to camphorquinone Macaca fascicularis isoascorbic acid
0.038
-
 mutant W254Y Macaca fascicularis isoascorbic acid
0.066
-
 mutant enzyme W254A, in 25 mM Tris-HCl pH 7.5, at 25°C Macaca fuscata isoascorbic acid
0.066
-
 mutant W254A Macaca fascicularis isoascorbic acid
0.075
-
 mutant enzyme F154A, in 25 mM Tris-HCl pH 7.5, at 25°C Macaca fuscata 4-hydroxyacetophenone
0.075
-
 rmutant F279A Macaca fascicularis 4-hydroxyacetophenone
0.078
-
 mutant enzyme F154A, in 25 mM Tris-HCl pH 7.5, at 25°C Macaca fuscata 4-hydroxyacetophenone
0.078
-
 mutant F154A Macaca fascicularis 4-hydroxyacetophenone
0.083
-
 mutant enzyme W254A, in 25 mM Tris-HCl pH 7.5, at 25°C Macaca fuscata 4-hydroxyacetophenone
0.083
-
 mutant W254A Macaca fascicularis 4-hydroxyacetophenone
0.136
-
 mutant enzyme W125Y, in 25 mM Tris-HCl pH 7.5, at 25°C Macaca fuscata 4-hydroxyacetophenone
0.136
-
 mutant W125Y Macaca fascicularis 4-hydroxyacetophenone
0.288
-
 mutant enzyme F154A, in 25 mM Tris-HCl pH 7.5, at 25°C Macaca fuscata isoascorbic acid
0.288
-
 mutant F154A Macaca fascicularis isoascorbic acid
3.94
-
 mutant enzyme F154A, in 25 mM Tris-HCl pH 7.5, at 25°C Macaca fuscata isoascorbic acid
3.94
-
 mutant F279A Macaca fascicularis isoascorbic acid
4.176
-
 mutant enzyme W125Y, in 25 mM Tris-HCl pH 7.5, at 25°C Macaca fuscata isoascorbic acid
4.176
-
 mutant W125Y Macaca fascicularis isoascorbic acid