Information on EC 1.8.1.15 - mycothione reductase

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The enzyme appears in viruses and cellular organisms

EC NUMBER
COMMENTARY hide
1.8.1.15
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RECOMMENDED NAME
GeneOntology No.
mycothione reductase
REACTION
REACTION DIAGRAM
COMMENTARY hide
ORGANISM
UNIPROT
LITERATURE
2 mycothiol + NAD(P)+ = mycothione + NAD(P)H + H+
show the reaction diagram
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REACTION TYPE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
oxidation
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redox reaction
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reduction
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PATHWAY
BRENDA Link
KEGG Link
MetaCyc Link
arsenate detoxification III (mycothiol)
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mycothiol oxidation
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SYSTEMATIC NAME
IUBMB Comments
mycothiol:NAD(P)+ oxidoreductase
Contains FAD. No activity with glutathione, trypanothione or coenzyme A as substrate.
GENERAL INFORMATION
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
malfunction
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in vivo Mtr knockout strain shows that the enzyme is involved in arsenate (As(V)) resistance suggesting a possible relation with the arsenate reductase activities
physiological function
SUBSTRATE
PRODUCT                       
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate) hide
LITERATURE
(Substrate)
COMMENTARY
(Product) hide
LITERATURE
(Product)
Reversibility
r=reversible
ir=irreversible
?=not specified
2,6-dimethylbenzoquinone + NADPH
?
show the reaction diagram
-
-
-
?
2-(-N-acetyl-L-cysteinyl) amino-2-deoxy-alpha-D-glucopyranoside disulfide + NADPH
?
show the reaction diagram
-
-
-
-
?
2-methyl-1,4-naphthoquinone + alpha-NADPH
?
show the reaction diagram
-
-
-
?
5,8-dihydroxy-1,4-naphthoquinone + NADPH
?
show the reaction diagram
-
-
-
?
5-(benzyl 2-(-N-acetyl-L-cysteinyl) amino-2-deoxy-alpha-D-glucopyranoside)-dithio-2-nitrobenzoate + NADPH
?
show the reaction diagram
-
a 5,5'-dithiobis-2-nitrobenzoic acid (DTNB)-coupled assay is developed. The mixed disulfide substrate liberates one molecule of TNB on NADPH-dependent reduction by Mycobacterium tubercolosis reductase. The liberated mycothiol analogue then reacts with DTNB to regenerate the mixed disulfide substrate and another molecule of TNB. Reaction progress can be measured by the increase in absorbance (412 nm) from the two molecules of TNB produced per turn of this catalytic cycle
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?
5-hydroxy-1,4-naphthoquinone + NADPH
?
show the reaction diagram
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-
?
7-methyljuglone + NADPH
?
show the reaction diagram
-
potent subversive substrate
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-
?
8-chloro-5-methoxy-7-methyl-1,4-naphthoquinone + NADPH
?
show the reaction diagram
-
-
-
-
?
AcCys-GlcN + NADPH
?
show the reaction diagram
-
-
-
-
?
AcCys-GlcN-1-O-CH2Ph + NADPH
?
show the reaction diagram
-
-
-
-
?
AcCys-GlcN-1-O-CH3 + NADPH
?
show the reaction diagram
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-
-
-
?
benzyl 2-(-N-acetyl-L-cysteinyl) amino-2-deoxy-alpha-D-glucopyranoside disulfide + NADPH
?
show the reaction diagram
-
-
-
-
?
benzyl 2-(N-acetyl-L-cysteinyl)amino-2-deoxy-alpha-D-glucopyranoside disulfide + NADPH
?
show the reaction diagram
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-
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-
?
des-myo-inositol mycothione + NADH
?
show the reaction diagram
des-myo-inositol mycothione + reduced beta-nicotinamide hypoxanthine dinucleotide
?
show the reaction diagram
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-
-
?
des-myo-inositol mycothione + reduced beta-nicotinamide hypoxanthine dinucleotide phosphate
?
show the reaction diagram
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?
des-myo-inositol mycothione + thio-NADH
?
show the reaction diagram
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?
des-myo-inositol mycothione + thio-NADPH
?
show the reaction diagram
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-
?
desmyoinositol mycothione + NADPH
?
show the reaction diagram
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?
dimeric mycothiol disulfide + NADPH
2 mycothione + H+
show the reaction diagram
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?
diospyrin + NADPH
?
show the reaction diagram
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subversive substrate
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?
DTNB + NADPH
?
show the reaction diagram
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-
?
juglone + NADPH
?
show the reaction diagram
-
subversive substrate
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-
?
menadione + NADPH
?
show the reaction diagram
-
subversive substrate
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?
methyl 2-(-N-acetyl-L-cysteinyl) amino-2-deoxy-alpha-D-glucopyranoside disulfide + NADPH
?
show the reaction diagram
-
-
-
-
?
mycothione + NADPH
mycothiol + NADP+
show the reaction diagram
mycothione + NADPH + H+
mycothiol + NADP+
show the reaction diagram
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-
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-
?
neodiospyrin + NADPH
?
show the reaction diagram
-
subversive substrate
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?
additional information
?
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many naphthoquinones operate as subversive substrates. The native functions of these enzyme involves the NADPH-dependent reduction of disulfide bonds in the substrate. The enzyme-mediated toxicity of quinones/naphthoquinones is a consequence of their enzymatic reduction to semiquinone radicals. The naphthoquinone is then regenerated via the concomitant reduction of oxygen to toxic superoxide anion radicals. In this manner the naphthoquinone substrate is regenerated and the futile redox cycle continues
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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
mycothione + NADPH
mycothiol + NADP+
show the reaction diagram
COFACTOR
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
NADPH
INHIBITORS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
2-(5-bromo-2-methoxyphenyl)acrylonitrile
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time-dependent inhibitor
DMSO
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in the presence of 4% (v/v) DMSO, Mycobacterium tubercolosis reductase activity is reduced by only 10%. It is recommended that the DMSO content in sets of inhibition assays should be kept at a constant with 4% (v/v) DMSO as the upper limit
KM VALUE [mM]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
4
2,6-dimethylbenzoquinone
-
0.463
2-(-N-acetyl-L-cysteinyl) amino-2-deoxy-alpha-D-glucopyranoside disulfide
-
30C, pH 7.5
0.24
2-methyl-1,4-naphthoquinone
-
0.34
5,8-Dihydroxy-1,4-naphthoquinone
-
0.268
5-(benzyl 2-(N-acetyl-L-cysteinyl) amino-2-deoxy-alpha-D-glucopyranoside)-dithio-2-nitrobenzoate
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-
0.54
5-hydroxy-1,4-naphthoquinone
-
2.365
7-methyljuglone
-
pH 7.6, 30C
0.142
8-chloro-5-methoxy-7-methyl-1,4-naphthoquinone
-
pH 7.6, 30C
0.055
alpha-NADPH
des-myo-inositol mycothione as second substrate
0.438
benzyl 2-(-N-acetyl-L-cysteinyl) amino-2-deoxy-alpha-D-glucopyranoside disulfide
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30C, pH 7.5
0.438
benzyl 2-(N-acetyl-L-cysteinyl) amino-2-deoxy-alpha-D-glucopyranoside disulfide
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-
0.008
beta-NADPH
des-myo-inositol mycothione as second substrate
0.4 - 0.51
des-myo-inositol mycothione
0.118
diospyrin
-
pH 7.6, 30C
1.088
juglone
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pH 7.6, 30C
0.732
menadione
-
pH 7.6, 30C
0.61
methyl 2-(-N-acetyl-L-cysteinyl) amino-2-deoxy-alpha-D-glucopyranoside disulfide
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30C, pH 7.5
0.073 - 0.113
mycothione
0.043
NADH
des-myo-inositol mycothione as second substrate
0.308
neodiospyrin
-
pH 7.6, 30C
0.2
reduced beta-nicotinamide hypoxanthine dinucleotide
des-myo-inositol mycothione as second substrate
0.023
reduced beta-nicotinamide hypoxanthine dinucleotide phosphate
des-myo-inositol mycothione as second substrate
0.09
thio-NADH
des-myo-inositol mycothione as second substrate
0.001
thio-NADPH
des-myo-inositol mycothione as second substrate
TURNOVER NUMBER [1/s]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
70.05
2-(-N-acetyl-L-cysteinyl) amino-2-deoxy-alpha-D-glucopyranoside disulfide
Mycobacterium tuberculosis
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30C, pH 7.5
115
5-(benzyl 2-(N-acetyl-L-cysteinyl) amino-2-deoxy-alpha-D-glucopyranoside)-dithio-2-nitrobenzoate
Mycobacterium tuberculosis
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-
0.254
7-methyljuglone
Mycobacterium tuberculosis
-
pH 7.6, 30C
0.435
8-chloro-5-methoxy-7-methyl-1,4-naphthoquinone
Mycobacterium tuberculosis
-
pH 7.6, 30C
36.99
benzyl 2-(-N-acetyl-L-cysteinyl) amino-2-deoxy-alpha-D-glucopyranoside disulfide
Mycobacterium tuberculosis
-
30C, pH 7.5
37
benzyl 2-(N-acetyl-L-cysteinyl) amino-2-deoxy-alpha-D-glucopyranoside disulfide
Mycobacterium tuberculosis
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-
0.033
diospyrin
Mycobacterium tuberculosis
-
pH 7.6, 30C
0.324
juglone
Mycobacterium tuberculosis
-
pH 7.6, 30C
0.483
menadione
Mycobacterium tuberculosis
-
pH 7.6, 30C
25.54
methyl 2-(-N-acetyl-L-cysteinyl) amino-2-deoxy-alpha-D-glucopyranoside disulfide
Mycobacterium tuberculosis
-
30C, pH 7.5
68.76 - 69
mycothione
20 - 30
NADH
190
NADP+
Mycobacterium tuberculosis
-
25C
129
NADPH
0.063
neodiospyrin
Mycobacterium tuberculosis
-
pH 7.6, 30C
kcat/KM VALUE [1/mMs-1]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.427
5-(benzyl 2-(N-acetyl-L-cysteinyl) amino-2-deoxy-alpha-D-glucopyranoside)-dithio-2-nitrobenzoate
Mycobacterium tuberculosis
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-
27222
0.09
benzyl 2-(N-acetyl-L-cysteinyl) amino-2-deoxy-alpha-D-glucopyranoside disulfide
Mycobacterium tuberculosis
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27223
0.61
mycothione
Mycobacterium tuberculosis
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8410
Ki VALUE [mM]
INHIBITOR
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
1.11
2-(5-bromo-2-methoxyphenyl)acrylonitrile
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kinact: 0.22/min
SPECIFIC ACTIVITY [µmol/min/mg]
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
pH OPTIMUM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
TEMPERATURE OPTIMUM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
SOURCE TISSUE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
SOURCE
-
gene is actively transcribed during logarithmic growth
Manually annotated by BRENDA team
MOLECULAR WEIGHT
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
50000
alpha2, 2 * 50000, SDS-PAGE
100000
gel filtration
SUBUNITS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
homodimer
alpha2, 2 * 50000, SDS-PAGE
Purification/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
Cloned/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
expressed in Escherichia coli as a His-tagged fusion protein
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expression in Mycobacterium smegmatis pyrF
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APPLICATION
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
analysis
medicine
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the enzyme is sensitive to free radical generating antituberculosis drugs and may be useful target for new drug development
molecular biology
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a DTNB-coupled assay is developed for time-dependent inhibition of Mycobacterium tubercolosis reductase employing a benzyl glycoside analogue of MSH, from which an efficient mixed disulfide substrate is chemically recycled in situ, thereby greatly reducing the substrate quantities needed for such assays
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