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Information on EC 1.1.1.274 - 2,5-didehydrogluconate reductase (2-dehydro-D-gluconate-forming)
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1.1.1.274 2,5-didehydrogluconate reductase (2-dehydro-D-gluconate-forming)IUBMB Comments
The enzyme is involved in the catabolism of 2,5-didehydrogluconate. cf. EC 1.1.1.346, 2,5-didehydrogluconate reductase (2-dehydro-L-gulonate-forming).
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Word Map
- 1.1.1.274
-
2,5-diketo-d-gluconic
- corynebacterium
-
2-keto-l-gulonic
-
nadph-dependent
-
aldo-keto
-
l-ascorbic
- d-glucose
- synthesis
- citrinum
-
penicillium
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activity-stained
- aldose
-
cofactor-binding
- reductases
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biocatalysis
- erwinia
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error-prone
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stereo-specific
- ascorbate
-
enantioselectivity
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two-phase
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pantoea
- citrea
- biotechnology
The expected taxonomic range for this enzyme is: Bacteria, Archaea, Eukaryota
Synonyms
2,5-dkg reductase, 2,5-dkg, 2,5-dkgr, 2,5-diketo-d-gluconate reductase, beta-keto ester reductase, yqhe reductase, 
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SYNONYM 
ORGANISM
UNIPROT
COMMENTARY 
LITERATURE
2,5-diketo-D-gluconate reductase
2,5-diketo-D-gluconic acid reductase
2,5-DKG
2,5DKGR
beta-keto ester reductase
CTATCC11996_22452
YqhE
YqhE reductase
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-
-
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2,5-diketo-D-gluconate reductase
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-
-
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REACTION
REACTION DIAGRAM
COMMENTARY
ORGANISM
UNIPROT
LITERATURE
2-dehydro-D-gluconate + NADP+ = 2,5-didehydro-D-gluconate + NADPH + H+
reaction mechanism
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2-dehydro-D-gluconate + NADP+ = 2,5-didehydro-D-gluconate + NADPH + H+
catalytic mechanism
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2-dehydro-D-gluconate + NADP+ = 2,5-didehydro-D-gluconate + NADPH + H+
enzyme also possesses beta-keto ester reductase activity
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2-dehydro-D-gluconate + NADP+ = 2,5-didehydro-D-gluconate + NADPH + H+
reaction mechanism of wild-type and F22Y/K232G/R238H/A272G mutant enzyme
2-dehydro-D-gluconate + NADP+ = 2,5-didehydro-D-gluconate + NADPH + H+
enzyme also possesses beta-keto ester reductase activity
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2-dehydro-D-gluconate + NADP+ = 2,5-didehydro-D-gluconate + NADPH + H+
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-
-
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REACTION TYPE
ORGANISM
UNIPROT
COMMENTARY
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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SYSTEMATIC NAME
IUBMB Comments
2-dehydro-D-gluconate:NADP+ 2-oxidoreductase (2-dehydro-D-gluconate-forming)
The enzyme is involved in the catabolism of 2,5-didehydrogluconate. cf. EC 1.1.1.346, 2,5-didehydrogluconate reductase (2-dehydro-L-gulonate-forming).
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CAS REGISTRY NUMBER
COMMENTARY
95725-95-4
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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
2,5-didehydro-D-gluconate + NADPH + H+
2-dehydro-D-gluconate + NADP+
-
-
-
?
ethyl 2-ethylacetoacetate + NADPH
ethyl (2R)-ethyl-(3S)-hydroxybutanoate + NADP+
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stereospecific reaction
-
-
?
ethyl 2-methylacetoacetate + NADPH
ethyl (2R)-methyl-(3S)-hydroxybutanoate + NADP+
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stereospecific reaction
-
-
?
ethyl acetoacetate + NADPH
ethyl (3S)-hydroxybutanoate + NADP+
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stereospecific reaction
-
-
?
ethyl-(2R)-allylacetoacetate + NADPH
?
-
250% of activity with ethyl-2-methylacetoacetate
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-
?
2,5-didehydro-D-gluconate + NADH
2-keto-L-gulonate + NAD+
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170fold lower reduction rate with NADH compared to NADPH
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?
2,5-didehydro-D-gluconate + NADH
2-keto-L-gulonate + NAD+
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170fold lower reduction rate with NADH compared to NADPH
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?
2,5-didehydro-D-gluconate + NADPH
2-keto-L-gulonate + NADP+
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-
-
?
2,5-didehydro-D-gluconate + NADPH
2-keto-L-gulonate + NADP+
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stereospecific reduction to 2-keto-L-gulonate, no activity with D-fructose, L-sorbose, 5-keto-D-gluconate, 2-keto-L-gulonate, 2-keto-D-gluconate, pyruvate or hydroxypyruvate
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r
2,5-didehydro-D-gluconate + NADPH
2-keto-L-gulonate + NADP+
-
stereospecific reduction to 2-keto-L-gulonate, no activity with D-fructose, L-sorbose, 5-keto-D-gluconate, 2-keto-L-gulonate, 2-keto-D-gluconate, pyruvate or hydroxypyruvate
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r
2,5-didehydro-D-gluconate + NADPH
2-keto-L-gulonate + NADP+
-
-
-
?
2,5-didehydro-D-gluconate + NADPH
2-keto-L-gulonate + NADP+
both isoenzymes A and B are specific for NADPH
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?
2,5-didehydro-D-gluconate + NADPH
2-keto-L-gulonate + NADP+
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-
-
?
2,5-didehydro-D-gluconate + NADPH
2-oxo-L-gulonic acid + NADP+
step in the biosynthesis of L-ascorbic acid
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-
?
2,5-didehydro-D-gluconate + NADPH
2-oxo-L-gulonic acid + NADP+
i.e. 2,5-diketo-D-gluconic acid or 2,5-DKG, stereospecific reaction
i.e. 2-keto-L-gulonic acid or 2-KLG, product is a precursor for L-ascorbic acid
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?
2-dehydro-D-gulonate + NADP+
2,5-didehydro-D-gluconate + NADPH + H+
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-
-
-
?
2-dehydro-D-gulonate + NADP+
2,5-didehydro-D-gluconate + NADPH + H+
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-
-
-
?
5-keto-D-fructose + NADPH
L-sorbose + NADP+
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isoenzymes I and II
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?
5-keto-D-fructose + NADPH
L-sorbose + NADP+
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isoenzymes I and II
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?
ethyl 2-methylacetoacetate + NADPH + H+
ethyl (2R)-methyl-(3S)-hydroxybutanoate + NADP+
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7% activity with NADH
-
?
ethyl 2-methylacetoacetate + NADPH + H+
ethyl (2R)-methyl-(3S)-hydroxybutanoate + NADP+
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7% activity with NADH
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?
ethyl-(2R)-ethylacetoacetate + NADPH
ethyl-(2R)-ethyl-(3S)-hydroxybutanoate + NADP+
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120% of activity with ethyl-2-methylacetoacetate
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?
ethyl-(2R)-ethylacetoacetate + NADPH
ethyl-(2R)-ethyl-(3S)-hydroxybutanoate + NADP+
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120% of activity with ethyl-2-methylacetoacetate
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?
ethylacetoacetate + NADPH
ethyl-(3S)-hydroxybutanoate + NADP+
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53% of activity with ethyl-2-methylacetoacetate
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?
ethylacetoacetate + NADPH
ethyl-(3S)-hydroxybutanoate + NADP+
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53% of activity with ethyl-2-methylacetoacetate
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?
additional information
?
-
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the enzyme catalyzes degradation of estradiol, estrone, testosterone, and methyltestosterone, overview
-
-
?
additional information
?
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the enzyme catalyzes degradation of estradiol, estrone, testosterone, and methyltestosterone, overview
-
-
?
additional information
?
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isozyme A is more stable than isozyme B but less active
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-
?
additional information
?
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substrate specificity, no activity with ethyl propionyl acetate and ethyl butyryl acetate
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-
?
additional information
?
-
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substrate specificity, no activity with ethyl propionyl acetate and ethyl butyryl acetate
-
-
?
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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
2,5-didehydro-D-gluconate + NADPH
2-oxo-L-gulonic acid + NADP+
step in the biosynthesis of L-ascorbic acid
-
-
?
2,5-didehydro-D-gluconate + NADPH + H+
2-dehydro-D-gluconate + NADP+
-
-
-
?
ethyl 2-ethylacetoacetate + NADPH
ethyl (2R)-ethyl-(3S)-hydroxybutanoate + NADP+
-
stereospecific reaction
-
-
?
ethyl 2-methylacetoacetate + NADPH
ethyl (2R)-methyl-(3S)-hydroxybutanoate + NADP+
-
stereospecific reaction
-
-
?
ethyl acetoacetate + NADPH
ethyl (3S)-hydroxybutanoate + NADP+
-
stereospecific reaction
-
-
?
2-dehydro-D-gulonate + NADP+
2,5-didehydro-D-gluconate + NADPH + H+
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-
-
-
?
2-dehydro-D-gulonate + NADP+
2,5-didehydro-D-gluconate + NADPH + H+
-
-
-
-
?
additional information
?
-
-
the enzyme catalyzes degradation of estradiol, estrone, testosterone, and methyltestosterone, overview
-
-
?
additional information
?
-
-
the enzyme catalyzes degradation of estradiol, estrone, testosterone, and methyltestosterone, overview
-
-
?
additional information
?
-
-
substrate specificity, no activity with ethyl propionyl acetate and ethyl butyryl acetate
-
-
?
additional information
?
-
-
substrate specificity, no activity with ethyl propionyl acetate and ethyl butyryl acetate
-
-
?
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COFACTOR
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
additional information
cofactor binding structure of wild-type and F22Y/K232G/R238H/A272G mutant enzyme, involved Lys232, Ala272, and Arg238
-
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INHIBITOR
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
2,5-didehydro-D-gluconate
substrate inhibition of isozyme B, not of isozyme A, at high concentrations
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DISEASE
TITLE OF PUBLICATION
LINK TO PUBMED
Acrodynia
Genetic and biochemical characterization of the pathway in Pantoea citrea leading to pink disease of pineapple.
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KM VALUE [mM]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
3.1
ethyl 2-methylacetoacetate
-
pH 7.0, 30°C, with a cofactor level 20fold higher than the Km value
0.39
2,5-didehydro-D-gluconate
-
F22Y/K232G/R235T/R238H/A272G isoenzyme A mutant
8.7
2,5-didehydro-D-gluconate
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F22Y/K232G/R235T/R238H/A272G isoenzyme A mutant
9.1
2,5-didehydro-D-gluconate
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F22Y/K232G/R238H/A272G isoenzyme A mutant
13
2,5-didehydro-D-gluconate
-
F22Y/K232G/R235G/R238E/A272G isoenzyme A mutant
27
2,5-didehydro-D-gluconate
-
F22Y/S232T/R235S/R238H/A272G isoenzyme A mutant
32
2,5-didehydro-D-gluconate
-
F22Y/K232G/R235G/R238H/A272G isoenzyme A mutant
43
2,5-didehydro-D-gluconate
-
F22Y/K232G/R235G/R238H/A272G isoenzyme A mutant
150
2,5-didehydro-D-gluconate
-
F22Y/K232G/R235T/R238E/A272G isoenzyme A mutant
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TURNOVER NUMBER [1/s]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
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Ki VALUE [mM]
INHIBITOR
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
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SPECIFIC ACTIVITY [µmol/min/mg]
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
0.01
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pH OPTIMUM
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
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pH RANGE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
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TEMPERATURE OPTIMUM
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
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