Information on EC 1.1.1.289 - sorbose reductase

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The expected taxonomic range for this enzyme is: Eukaryota, Bacteria

EC NUMBER
COMMENTARY
1.1.1.289
-
RECOMMENDED NAME
GeneOntology No.
sorbose reductase
REACTION
REACTION DIAGRAM
COMMENTARY
ORGANISM
UNIPROT ACCESSION NO.
LITERATURE
D-glucitol + NADP+ = L-sorbose + NADPH + H+
show the reaction diagram
-
-
-
-
PATHWAY
KEGG Link
MetaCyc Link
galactose degradation IV
-
SYSTEMATIC NAME
IUBMB Comments
D-glucitol:NADP+ oxidoreductase
The reaction occurs predominantly in the reverse direction. This enzyme can also convert D-fructose into D-mannitol, but more slowly. Belongs in the short-chain dehydrogenase family.
SYNONYMS
ORGANISM
UNIPROT ACCESSION NO.
COMMENTARY
LITERATURE
FAD-dependent D-sorbitol dehydrogenase
-
-
FAD-dependent D-sorbitol dehydrogenase
Gluconobacter frateurii THD32
-
-
-
flavin adenine dinucleotide-dependent D-sorbitol dehydrogenase
-
-
flavin adenine dinucleotide-dependent D-sorbitol dehydrogenase
Gluconobacter frateurii THD32
-
-
-
L-sorbose reductase
A4PB64
-
L-sorbose reductase
-
-
L-sorbose reductase
Gluconobacter oxydans IFO 3294
-
-
-
NADPH-dependent L-sorbose reductase
-
-
NADPH-dependent L-sorbose reductase
Gluconobacter frateurii THD32
-
-
-
NADPH-dependent sorbose reductase
-
-
SboA
Gluconobacter frateurii THD32
-
-
-
SLDH
Gluconobacter frateurii THD32
-
-
-
CAS REGISTRY NUMBER
COMMENTARY
138440-90-1
-
ORGANISM
COMMENTARY
LITERATURE
SEQUENCE CODE
SEQUENCE DB
SOURCE
recombinant enzyme with FLAG-tag
-
-
Manually annotated by BRENDA team
strain THD32, NBRC 101656, genes sldSLC and sboA
-
-
Manually annotated by BRENDA team
Gluconobacter frateurii THD32
strain THD32, NBRC 101656, genes sldSLC and sboA
-
-
Manually annotated by BRENDA team
strain IFO 3291
-
-
Manually annotated by BRENDA team
strain IFO 3294
-
-
Manually annotated by BRENDA team
strain N44-1
-
-
Manually annotated by BRENDA team
Gluconobacter oxydans IFO 3291
strain IFO 3291
-
-
Manually annotated by BRENDA team
Gluconobacter oxydans IFO 3294
strain IFO 3294
-
-
Manually annotated by BRENDA team
Gluconobacter oxydans N44-1
strain N44-1
-
-
Manually annotated by BRENDA team
SUBSTRATE
PRODUCT                      
REACTION DIAGRAM
ORGANISM
UNIPROT ACCESSION NO.
COMMENTARY
(Substrate)
LITERATURE
(Substrate)
COMMENTARY
(Product)
LITERATURE
(Product)
Reversibility
r=reversible
ir=irreversible
?=not specified
5-keto-D-fructose + NADPH
? + NADP+
show the reaction diagram
Gluconobacter oxydans, Gluconobacter oxydans N44-1
-
86.8% of the rate with L-sorbose
-
-
r
D-fructose + NADPH
D-mannitol + NADP+
show the reaction diagram
-
-
-
-
-
D-fructose + NADPH
D-mannitol + NADP+
show the reaction diagram
-
less effective than reaction with L-sorbose
-
-
?
D-fructose + NADPH
D-mannitol + NADP+
show the reaction diagram
Gluconobacter oxydans N44-1
-
-
-
-
-
D-glucitol + NADP+
D-sorbose + NADPH
show the reaction diagram
Gluconobacter frateurii, Gluconobacter frateurii THD32
-
-
-
-
r
D-glucitol + NADP+
L-sorbose + NADPH
show the reaction diagram
Gluconobacter frateurii, Gluconobacter frateurii THD32
-
-
-
-
r
D-mannitol + NADP+
L-fructose + NADPH + H+
show the reaction diagram
Gluconobacter oxydans, Gluconobacter oxydans N44-1
-
134% of the rate with L-sorbose
-
-
r
D-mannitol + NADP+
D-mannose + NADPH + H+
show the reaction diagram
-
-
-
-
r
D-sorbitol + NADP+
L-sorbose + NADPH + H+
show the reaction diagram
-
-
-
-
r
D-sorbitol + NADP+
L-sorbose + NADPH + H+
show the reaction diagram
-
-
-
-
r
D-sorbitol + NADP+
L-sorbose + NADPH + H+
show the reaction diagram
-
134% of the rate with L-sorbose
-
-
r
D-sorbitol + NADP+
L-sorbose + NADPH + H+
show the reaction diagram
-
low efficiency
-
-
?
D-sorbitol + NADP+
L-sorbose + NADPH + H+
show the reaction diagram
Gluconobacter oxydans IFO 3294
-
-
-
-
r
D-sorbitol + NADP+
L-sorbose + NADPH + H+
show the reaction diagram
Gluconobacter oxydans N44-1
-
134% of the rate with L-sorbose
-
-
r
D-xylitol + NADP+
D-xylose + NADPH + H+
show the reaction diagram
-
-
-
-
r
erythritol + NADP+
? + NADPH
show the reaction diagram
Gluconobacter oxydans, Gluconobacter oxydans N44-1
-
65.3% of the rate with L-sorbose
-
-
r
L-fructose + NADPH
D-mannitol + NADP+
show the reaction diagram
-
142% of the rate with L-sorbose
-
-
r
L-sorbose + NADPH
L-sorbitol + NADP+
show the reaction diagram
-
-
-
-
?
L-sorbose + NADPH
D-sorbitol + NADP+
show the reaction diagram
-
-
-
-
r
L-sorbose + NADPH
D-sorbitol + NADP+
show the reaction diagram
Gluconobacter oxydans IFO 3294
-
-
-
-
r
ribulose + NADPH
? + NADP+
show the reaction diagram
-
2.4% of the rate with L-sorbose
-
-
r
tagatose + NADPH
? + NADP+
show the reaction diagram
-
0.8% of the rate with L-sorbose
-
-
r
xylulose + NADPH
? + NADP+
show the reaction diagram
-
25.7% of the rate with L-sorbose
-
-
r
L-sorbose + NADPH + H+
L-sorbitol + NADP+
show the reaction diagram
A4PB64
-
-
-
?
additional information
?
-
-
highly specific for D-sorbitol and L-sorbose. Reaction rate in L-sorbose reduction highly predominates over L-sorbitol oxidation over a wide pH range
-
-
-
additional information
?
-
-
development of a substrate-coupled biocatalytic process driven by NADPH-dependent sorbose reductase for the asymmetric reduction of ethyl 4-chloro-3-oxobutanoate, overview. Ethyl 4-chloro-3-oxobutanoate is reduced to (S)-4-chloro-3-hydroxybutanoate, while NADPH is regenerated by the enzyme via oxidation of sorbitol, mannitol, or xylitol in crude extract of recombinant Escherichia coli cells, overview
-
-
-
additional information
?
-
Gluconobacter oxydans IFO 3294
-
highly specific for D-sorbitol and L-sorbose. Reaction rate in L-sorbose reduction highly predominates over L-sorbitol oxidation over a wide pH range
-
-
-
NATURAL SUBSTRATES
NATURAL PRODUCTS
REACTION DIAGRAM
ORGANISM
UNIPROT ACCESSION NO.
COMMENTARY
(Substrate)
LITERATURE
(Substrate)
COMMENTARY
(Product)
LITERATURE
(Product)
REVERSIBILITY
r=reversible
ir=irreversible
?=not specified
D-glucitol + NADP+
D-sorbose + NADPH
show the reaction diagram
-
-
-
-
r
D-glucitol + NADP+
L-sorbose + NADPH
show the reaction diagram
-
-
-
-
r
D-glucitol + NADP+
D-sorbose + NADPH
show the reaction diagram
Gluconobacter frateurii THD32
-
-
-
-
r
D-glucitol + NADP+
L-sorbose + NADPH
show the reaction diagram
Gluconobacter frateurii THD32
-
-
-
-
r
D-sorbitol + NADP+
L-sorbose + NADPH + H+
show the reaction diagram
-
-
-
-
r
COFACTOR
ORGANISM
UNIPROT ACCESSION NO.
COMMENTARY
LITERATURE
IMAGE
NADP+
-
dependent on
NADPH
-
dependent on
NADPH
-
dependent on
additional information
-
no cofactor: NAD+, NADH
-
INHIBITORS
ORGANISM
UNIPROT ACCESSION NO.
COMMENTARY
LITERATURE
IMAGE
N-ethylmaleimide
-
0.97 mM, 81% residual activity
Na2HAsO4
-
0.97 mM, 90% residual activity
p-chloromercuribenzoate
-
0.19 mM, 43% residual activity
Quinine
-
0.49 mM, complete loss of activity
Sodium azide
-
0.97 mM, 90% residual activity
additional information
-
not inhibitory: sodium fluoroacetate, sodium fluoride, KCN, monoiodoacetate
-
KM VALUE [mM]
KM VALUE [mM] Maximum
SUBSTRATE
ORGANISM
UNIPROT ACCESSION NO.
COMMENTARY
LITERATURE
IMAGE
160
-
D-fructose
-
pH 7.0, 25C
1873
-
D-fructose
-
K0.5-value, positive cooperativity
7.3
-
D-Mannitol
-
pH 10.0, 25C
167
-
D-Sorbitol
-
pH 10.0, 25C
35
-
L-sorbose
-
pH 6.0, 25C
328
-
L-sorbose
-
pH 7.0, 25C
3953
-
L-sorbose
-
pH 7.5, 25C
0.032
-
NADPH
-
pH 6.0, 25C
0.111
-
NADPH
-
pH 7.0, 25C
TURNOVER NUMBER [1/s]
TURNOVER NUMBER MAXIMUM[1/s]
SUBSTRATE
ORGANISM
UNIPROT ACCESSION NO.
COMMENTARY
LITERATURE
IMAGE
154
-
D-fructose
-
pH 7.5, 25C, positive cooperativity
782
-
L-sorbose
-
pH 7.5, 25C, Michaelis-Menten kinetics
SPECIFIC ACTIVITY [µmol/min/mg]
SPECIFIC ACTIVITY MAXIMUM
ORGANISM
UNIPROT ACCESSION NO.
COMMENTARY
LITERATURE
2.93
-
-
substrate D-sorbitol, pH 6.2, 25C
33.1
-
-
substrate D-fructose, pH 6.2, 25C
77
-
-
pH 6.0, 25C, substrate L-sorbose
145
-
-
substrate L-sorbose, pH 6.2, 25C
pH OPTIMUM
pH MAXIMUM
ORGANISM
UNIPROT ACCESSION NO.
COMMENTARY
LITERATURE
6
7
-
oxidation of L-sorbitol
6
-
-
reduction of L-sorbose
6.2
-
-
assay at
7
-
-
reduction of L-sorbose
8
-
-
oxidation of D-sorbitol
9
-
-
reduction reaction, assay at
10
10.5
-
oxidation of D-sorbitol
10
-
-
oxidation of D-sorbitol
pH RANGE
pH RANGE MAXIMUM
ORGANISM
UNIPROT ACCESSION NO.
COMMENTARY
LITERATURE
5
7
-
reduction of L-sorbose
7
9
-
oxidation of D-sorbitol
TEMPERATURE OPTIMUM
TEMPERATURE OPTIMUM MAXIMUM
ORGANISM
UNIPROT ACCESSION NO.
COMMENTARY
LITERATURE
30
-
-
assay at
pI VALUE
pI VALUE MAXIMUM
ORGANISM
UNIPROT ACCESSION NO.
COMMENTARY
LITERATURE
4.8
-
-
isoelectric focusing and calculated
5.72
-
-
SboA, sequence calculation
SOURCE TISSUE
ORGANISM
UNIPROT ACCESSION NO.
COMMENTARY
LITERATURE
SOURCE
additional information
-
SboA is required for effective growth on D- or L-sorbose, the organism also grows on glycerol
Manually annotated by BRENDA team
additional information
Gluconobacter frateurii THD32
-
SboA is required for effective growth on D- or L-sorbose, the organism also grows on glycerol
-
Manually annotated by BRENDA team
LOCALIZATION
ORGANISM
UNIPROT ACCESSION NO.
COMMENTARY
GeneOntology No.
LITERATURE
SOURCE
Gluconobacter frateurii THD32
-
-
-
Manually annotated by BRENDA team
Gluconobacter oxydans IFO 3294, Gluconobacter oxydans N44-1
-
-
-
Manually annotated by BRENDA team
Gluconobacter frateurii THD32
-
-
-
Manually annotated by BRENDA team
MOLECULAR WEIGHT
MOLECULAR WEIGHT MAXIMUM
ORGANISM
UNIPROT ACCESSION NO.
COMMENTARY
LITERATURE
58000
-
-
gel filtration
60000
-
-
gel filtration
87000
-
-
recombinant SboA, gel filtration
124000
-
-
MALDI-TOF
SUBUNITS
ORGANISM
UNIPROT ACCESSION NO.
COMMENTARY
LITERATURE
dimer
-
2 * 30000, SDS-PAGE
dimer
Gluconobacter oxydans IFO 3294
-
2 * 30000, SDS-PAGE
-
monomer
-
1 * 60000, SDS-PAGE
monomer
Gluconobacter oxydans N44-1
-
1 * 60000, SDS-PAGE
-
tetramer
-
4 * 31000, SDS-PAGE and calculated
trimer
-
3 * 29000, recombinant SboA, SDS-PAGE, 3 * 28320, SboA, sequence calculation
trimer
Gluconobacter frateurii THD32
-
3 * 29000, recombinant SboA, SDS-PAGE, 3 * 28320, SboA, sequence calculation
-
Crystallization/COMMENTARY
ORGANISM
UNIPROT ACCESSION NO.
LITERATURE
in complex with L-sorbose or NADPH using the sitting-drop vapour-diffusion method, at 20C, to 2.38 and 1.90 A resolution, respectively. Crystal of the L-sorbose reductase-L-sorbose complex belongs to space group C2221, with unit-cell parameters a=124.2, b=124.1, c=60.8 A. The crystal of the L-sorbose reductase-NADPH complex belongs to space group P21, with unit-cell parameters a=124.3, b=61.0, c=124.5A, beta= 89.99. The crystals contain two and eight molecules, respectively, in the asymmetric unit
A4PB64
pH STABILITY
pH STABILITY MAXIMUM
ORGANISM
UNIPROT ACCESSION NO.
COMMENTARY
LITERATURE
6.5
7.5
-
30C, stable for 30 min
TEMPERATURE STABILITY
TEMPERATURE STABILITY MAXIMUM
ORGANISM
UNIPROT ACCESSION NO.
COMMENTARY
LITERATURE
30
-
-
pH 6.5-7.5, 30 min, stable
55
-
-
stable up to, for 10 min
65
-
-
2 min, more than 90% inactivation
STORAGE STABILITY
ORGANISM
UNIPROT ACCESSION NO.
LITERATURE
-20C, 0.01 M potassium buffer, pH 7.0, stable for at least one month
-
Purification/COMMENTARY
ORGANISM
UNIPROT ACCESSION NO.
LITERATURE
recombinant enzyme with FLAG-tag
-
by sonication, centrifugation and gel filtration
A4PB64
Cloned/COMMENTARY
ORGANISM
UNIPROT ACCESSION NO.
LITERATURE
expression in Escherichia coli strain Rosseta (DE3)
-
genes sldSLC and sboA, DNA and amino acid sequence determination and analysis, genetic organization, a putational transcription regulator encoded by gene sboR is located upstream, sboRA comprises an operon, expression of wild-type and mutant enzymes in Escherichia coli strain BL21(DE3)
-
into the HindIII/NotI site of pET-28a(+) plasmid, expression construct is designed to overexpress only L-sorbose reductase protein (residues 1-263), overexpressed in Escherichia coli BL21 (DE3) cells
A4PB64
ENGINEERING
ORGANISM
UNIPROT ACCESSION NO.
COMMENTARY
LITERATURE
additional information
-
construction of disruption mutants, a mutant defective in sboA shows significantly reduced growth on L-sorbose, while a sboR mutant grows on L-sorbose even better than the wild-type strain with higher NADPH-SR activity in cytoplasm fractions
additional information
Gluconobacter frateurii THD32
-
construction of disruption mutants, a mutant defective in sboA shows significantly reduced growth on L-sorbose, while a sboR mutant grows on L-sorbose even better than the wild-type strain with higher NADPH-SR activity in cytoplasm fractions
-
additional information
-
gene disruption mutant, no enzymic activity, no assimilation of once-produced L-sorbose
additional information
Gluconobacter oxydans IFO 3291
-
gene disruption mutant, no enzymic activity, no assimilation of once-produced L-sorbose
-
APPLICATION
ORGANISM
UNIPROT ACCESSION NO.
COMMENTARY
LITERATURE
synthesis
-
usage of a substrate-coupled biocatalytic process driven by an NADPH-dependent sorbose reductase from Candida albicans for the asymmetric reduction of ethyl 4-chloro-3-oxobutanoate