BRENDA - Enzyme Database show
show all sequences of 2.5.1.34

Actions of tryptophan prenyltransferases toward fumiquinazolines and their potential application for the generation of prenylated derivatives by combining chemical and chemoenzymatic syntheses

Mai, P.; Zocher, G.; Ludwig, L.; Stehle, T.; Li, S.; Adv. Synth. Catal. 358, 1639 -1653 (2016)
No PubMed abstract available

Data extracted from this reference:

Application
Application
Commentary
Organism
synthesis
possibility of producing prenylated analogues of ardeemin fumiquinazoline, a precursor of the multidrug resistance (MDR) export pump inhibitor ardeemin, by using dimethylallydiphosphate transferase enzymes, e.g. 4-DMATS, overview
Aspergillus fumigatus
Engineering
Amino acid exchange
Commentary
Organism
M328L
site-directed mutagenesis, the FgaPT2 mutant shows increased activity with L-tyrosine compared to the wild-type enzyme
Aspergillus fumigatus
Y398F
site-directed mutagenesis, the FgaPT2 mutant shows increased activity with L-tyrosine compared to the wild-type enzyme
Aspergillus fumigatus
KM Value [mM]
KM Value [mM]
KM Value Maximum [mM]
Substrate
Commentary
Organism
Structure
0.011
-
ent-ardeemin fumiquinazoline
pH 7.5, 37C, wild-type enzyme
Aspergillus fumigatus
0.032
-
ardeemin fumiquinazoline
pH 7.5, 37C, wild-type enzyme
Aspergillus fumigatus
0.055
-
dia-ardeemin fumiquinazoline
pH 7.5, 37C, wild-type enzyme
Aspergillus fumigatus
Natural Substrates/ Products (Substrates)
Natural Substrates
Organism
Commentary (Nat. Sub.)
Natural Products
Commentary (Nat. Pro.)
Organism (Nat. Pro.)
Reversibility
dimethylallyl diphosphate + L-tryptophan
Aspergillus fumigatus
-
diphosphate + 4-(3-methylbut-2-enyl)-L-tryptophan
-
-
?
Organism
Organism
Primary Accession No. (UniProt)
Commentary
Textmining
Aspergillus fumigatus
Q50EL0
gene 4-DMATS
-
Substrates and Products (Substrate)
Substrates
Commentary Substrates
Literature (Substrates)
Organism
Products
Commentary (Products)
Literature (Products)
Organism (Products)
Reversibility
dimethylallyl diphosphate + ardeemin fumiquinazoline
-
737407
Aspergillus fumigatus
diphosphate + (1S,4R)-4-methyl-1-[[4-(3-methylbut-2-en-1-yl)-1H-indol-3-yl]methyl]-2H-pyrazino[2,1-b]quinazoline-3,6(1H,4H)-dione + (1S,4R)-4-methyl-1-[[5-(3-methylbut-2-en-1-yl)-1H-indol-3-yl]methyl]-2H-pyrazino[2,1-b]quinazoline-3,6(1H,4H)-dione
-
-
-
?
dimethylallyl diphosphate + dia,ent-ardeemin fumiquinazoline
-
737407
Aspergillus fumigatus
diphosphate + (1R,4R)-4-methyl-1-[[4-(3-methylbut-2-en-1-yl)-1H-indol-3-yl]methyl]-2H-pyrazino[2,1-b]quinazoline-3,6(1H,4H)-dione + (1R,4R)-4-methyl-1-[[5-(3-methylbut-2-en-1-yl)-1H-indol-3-yl]methyl]-2H-pyrazino[2,1-b]quinazoline-3,6(1H,4H)-dione
-
-
-
?
dimethylallyl diphosphate + dia-ardeemin fumiquinazoline
-
737407
Aspergillus fumigatus
diphosphate + (1S,4S)-4-methyl-1-[[4-(3-methylbut-2-en-1-yl)-1H-indol-3-yl]methyl]-2H-pyrazino[2,1-b]quinazoline-3,6(1H,4H)-dione + (1S,4S)-4-methyl-1-[[5-(3-methylbut-2-en-1-yl)-1H-indol-3-yl]methyl]-2H-pyrazino[2,1-b]quinazoline-3,6(1H,4H)-dione
-
-
-
?
dimethylallyl diphosphate + ent-ardeemin fumiquinazoline
-
737407
Aspergillus fumigatus
diphosphate + (1R,4S)-4-methyl-1-[[4-(3-methylbut-2-en-1-yl)-1H-indol-3-yl]methyl]-2H-pyrazino[2,1-b]quinazoline-3,6(1H,4H)-dione + (1R,4S)-4-methyl-1-[[5-(3-methylbut-2-en-1-yl)-1H-indol-3-yl]methyl]-2H-pyrazino[2,1-b]quinazoline-3,6(1H,4H)-dione + (1R,4S)-4-methyl-1-[[6-(3-methylbut-2-en-1-yl)-1H-indol-3-yl]methyl]-2H-pyrazino[2,1-b]quinazoline-3,6(1H,4H)-dione
-
-
-
?
dimethylallyl diphosphate + L-tryptophan
-
737407
Aspergillus fumigatus
diphosphate + 4-(3-methylbut-2-enyl)-L-tryptophan
-
-
-
?
dimethylallyl diphosphate + L-tyrosine
low activity with the wild-type enzyme, higher activity with the enzyme mutantsM328L and Y398F
737407
Aspergillus fumigatus
diphosphate + 3-(3-methylbut-2-enyl)-L-tyrosine
-
-
-
?
Temperature Optimum [C]
Temperature Optimum [C]
Temperature Optimum Maximum [C]
Commentary
Organism
37
-
assay at
Aspergillus fumigatus
Temperature Stability [C]
Temperature Stability Minimum [C]
Temperature Stability Maximum [C]
Commentary
Organism
37
-
purified enzyme, pH 7.5, 4 h, 20% activity remaining
Aspergillus fumigatus
Turnover Number [1/s]
Turnover Number Minimum [1/s]
Turnover Number Maximum [1/s]
Substrate
Commentary
Organism
Structure
0.0016
-
ent-ardeemin fumiquinazoline
pH 7.5, 37C, wild-type enzyme
Aspergillus fumigatus
0.009
-
ardeemin fumiquinazoline
pH 7.5, 37C, wild-type enzyme
Aspergillus fumigatus
0.009
-
dia-ardeemin fumiquinazoline
pH 7.5, 37C, wild-type enzyme
Aspergillus fumigatus
pH Optimum
pH Optimum Minimum
pH Optimum Maximum
Commentary
Organism
7.5
-
assay at
Aspergillus fumigatus
Application (protein specific)
Application
Commentary
Organism
synthesis
possibility of producing prenylated analogues of ardeemin fumiquinazoline, a precursor of the multidrug resistance (MDR) export pump inhibitor ardeemin, by using dimethylallydiphosphate transferase enzymes, e.g. 4-DMATS, overview
Aspergillus fumigatus
Engineering (protein specific)
Amino acid exchange
Commentary
Organism
M328L
site-directed mutagenesis, the FgaPT2 mutant shows increased activity with L-tyrosine compared to the wild-type enzyme
Aspergillus fumigatus
Y398F
site-directed mutagenesis, the FgaPT2 mutant shows increased activity with L-tyrosine compared to the wild-type enzyme
Aspergillus fumigatus
KM Value [mM] (protein specific)
KM Value [mM]
KM Value Maximum [mM]
Substrate
Commentary
Organism
Structure
0.011
-
ent-ardeemin fumiquinazoline
pH 7.5, 37C, wild-type enzyme
Aspergillus fumigatus
0.032
-
ardeemin fumiquinazoline
pH 7.5, 37C, wild-type enzyme
Aspergillus fumigatus
0.055
-
dia-ardeemin fumiquinazoline
pH 7.5, 37C, wild-type enzyme
Aspergillus fumigatus
Natural Substrates/ Products (Substrates) (protein specific)
Natural Substrates
Organism
Commentary (Nat. Sub.)
Natural Products
Commentary (Nat. Pro.)
Organism (Nat. Pro.)
Reversibility
dimethylallyl diphosphate + L-tryptophan
Aspergillus fumigatus
-
diphosphate + 4-(3-methylbut-2-enyl)-L-tryptophan
-
-
?
Substrates and Products (Substrate) (protein specific)
Substrates
Commentary Substrates
Literature (Substrates)
Organism
Products
Commentary (Products)
Literature (Products)
Organism (Products)
Reversibility
dimethylallyl diphosphate + ardeemin fumiquinazoline
-
737407
Aspergillus fumigatus
diphosphate + (1S,4R)-4-methyl-1-[[4-(3-methylbut-2-en-1-yl)-1H-indol-3-yl]methyl]-2H-pyrazino[2,1-b]quinazoline-3,6(1H,4H)-dione + (1S,4R)-4-methyl-1-[[5-(3-methylbut-2-en-1-yl)-1H-indol-3-yl]methyl]-2H-pyrazino[2,1-b]quinazoline-3,6(1H,4H)-dione
-
-
-
?
dimethylallyl diphosphate + dia,ent-ardeemin fumiquinazoline
-
737407
Aspergillus fumigatus
diphosphate + (1R,4R)-4-methyl-1-[[4-(3-methylbut-2-en-1-yl)-1H-indol-3-yl]methyl]-2H-pyrazino[2,1-b]quinazoline-3,6(1H,4H)-dione + (1R,4R)-4-methyl-1-[[5-(3-methylbut-2-en-1-yl)-1H-indol-3-yl]methyl]-2H-pyrazino[2,1-b]quinazoline-3,6(1H,4H)-dione
-
-
-
?
dimethylallyl diphosphate + dia-ardeemin fumiquinazoline
-
737407
Aspergillus fumigatus
diphosphate + (1S,4S)-4-methyl-1-[[4-(3-methylbut-2-en-1-yl)-1H-indol-3-yl]methyl]-2H-pyrazino[2,1-b]quinazoline-3,6(1H,4H)-dione + (1S,4S)-4-methyl-1-[[5-(3-methylbut-2-en-1-yl)-1H-indol-3-yl]methyl]-2H-pyrazino[2,1-b]quinazoline-3,6(1H,4H)-dione
-
-
-
?
dimethylallyl diphosphate + ent-ardeemin fumiquinazoline
-
737407
Aspergillus fumigatus
diphosphate + (1R,4S)-4-methyl-1-[[4-(3-methylbut-2-en-1-yl)-1H-indol-3-yl]methyl]-2H-pyrazino[2,1-b]quinazoline-3,6(1H,4H)-dione + (1R,4S)-4-methyl-1-[[5-(3-methylbut-2-en-1-yl)-1H-indol-3-yl]methyl]-2H-pyrazino[2,1-b]quinazoline-3,6(1H,4H)-dione + (1R,4S)-4-methyl-1-[[6-(3-methylbut-2-en-1-yl)-1H-indol-3-yl]methyl]-2H-pyrazino[2,1-b]quinazoline-3,6(1H,4H)-dione
-
-
-
?
dimethylallyl diphosphate + L-tryptophan
-
737407
Aspergillus fumigatus
diphosphate + 4-(3-methylbut-2-enyl)-L-tryptophan
-
-
-
?
dimethylallyl diphosphate + L-tyrosine
low activity with the wild-type enzyme, higher activity with the enzyme mutantsM328L and Y398F
737407
Aspergillus fumigatus
diphosphate + 3-(3-methylbut-2-enyl)-L-tyrosine
-
-
-
?
Temperature Optimum [C] (protein specific)
Temperature Optimum [C]
Temperature Optimum Maximum [C]
Commentary
Organism
37
-
assay at
Aspergillus fumigatus
Temperature Stability [C] (protein specific)
Temperature Stability Minimum [C]
Temperature Stability Maximum [C]
Commentary
Organism
37
-
purified enzyme, pH 7.5, 4 h, 20% activity remaining
Aspergillus fumigatus
Turnover Number [1/s] (protein specific)
Turnover Number Minimum [1/s]
Turnover Number Maximum [1/s]
Substrate
Commentary
Organism
Structure
0.0016
-
ent-ardeemin fumiquinazoline
pH 7.5, 37C, wild-type enzyme
Aspergillus fumigatus
0.009
-
ardeemin fumiquinazoline
pH 7.5, 37C, wild-type enzyme
Aspergillus fumigatus
0.009
-
dia-ardeemin fumiquinazoline
pH 7.5, 37C, wild-type enzyme
Aspergillus fumigatus
pH Optimum (protein specific)
pH Optimum Minimum
pH Optimum Maximum
Commentary
Organism
7.5
-
assay at
Aspergillus fumigatus
General Information
General Information
Commentary
Organism
metabolism
dimethylallyltryptophan synthases (DMATSs) catalyze regiospecific transfer reactions of a prenyl moiety from dimethylallyl diphosphate to various positions of the indole ring of tryptophan. The 4-DMATS enzyme FgaPT2 is involved in biosynthesis of fumigaclavine C
Aspergillus fumigatus
additional information
possibility of producing prenylated analogues of ardeemin fumiquinazoline, a precursor of the multidrug resistance (MDR) export pump inhibitor ardeemin, by using dimethylallydiphosphate transferase enzymes, e.g. 4-DMATS, docking study of FgaPT2 with ardeemin fumiquinazoline and its stereoisomers, overview
Aspergillus fumigatus
General Information (protein specific)
General Information
Commentary
Organism
metabolism
dimethylallyltryptophan synthases (DMATSs) catalyze regiospecific transfer reactions of a prenyl moiety from dimethylallyl diphosphate to various positions of the indole ring of tryptophan. The 4-DMATS enzyme FgaPT2 is involved in biosynthesis of fumigaclavine C
Aspergillus fumigatus
additional information
possibility of producing prenylated analogues of ardeemin fumiquinazoline, a precursor of the multidrug resistance (MDR) export pump inhibitor ardeemin, by using dimethylallydiphosphate transferase enzymes, e.g. 4-DMATS, docking study of FgaPT2 with ardeemin fumiquinazoline and its stereoisomers, overview
Aspergillus fumigatus
Other publictions for EC 2.5.1.34
No.
1st author
Pub Med
title
organims
journal
volume
pages
year
Activating Compound
Application
Cloned(Commentary)
Crystallization (Commentary)
Engineering
General Stability
Inhibitors
KM Value [mM]
Localization
Metals/Ions
Molecular Weight [Da]
Natural Substrates/ Products (Substrates)
Organic Solvent Stability
Organism
Oxidation Stability
Posttranslational Modification
Purification (Commentary)
Reaction
Renatured (Commentary)
Source Tissue
Specific Activity [micromol/min/mg]
Storage Stability
Substrates and Products (Substrate)
Subunits
Temperature Optimum [C]
Temperature Range [C]
Temperature Stability [C]
Turnover Number [1/s]
pH Optimum
pH Range
pH Stability
Cofactor
Ki Value [mM]
pI Value
IC50 Value
Activating Compound (protein specific)
Application (protein specific)
Cloned(Commentary) (protein specific)
Cofactor (protein specific)
Crystallization (Commentary) (protein specific)
Engineering (protein specific)
General Stability (protein specific)
IC50 Value (protein specific)
Inhibitors (protein specific)
Ki Value [mM] (protein specific)
KM Value [mM] (protein specific)
Localization (protein specific)
Metals/Ions (protein specific)
Molecular Weight [Da] (protein specific)
Natural Substrates/ Products (Substrates) (protein specific)
Organic Solvent Stability (protein specific)
Oxidation Stability (protein specific)
Posttranslational Modification (protein specific)
Purification (Commentary) (protein specific)
Renatured (Commentary) (protein specific)
Source Tissue (protein specific)
Specific Activity [micromol/min/mg] (protein specific)
Storage Stability (protein specific)
Substrates and Products (Substrate) (protein specific)
Subunits (protein specific)
Temperature Optimum [C] (protein specific)
Temperature Range [C] (protein specific)
Temperature Stability [C] (protein specific)
Turnover Number [1/s] (protein specific)
pH Optimum (protein specific)
pH Range (protein specific)
pH Stability (protein specific)
pI Value (protein specific)
Expression
General Information
General Information (protein specific)
Expression (protein specific)
KCat/KM [mM/s]
KCat/KM [mM/s] (protein specific)
737407
Mai
-
Actions of tryptophan prenyltr ...
Aspergillus fumigatus
Adv. Synth. Catal.
358
1639 -1653
2016
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737544
Fan
Impacts and perspectives of pr ...
Aspergillus fumigatus
Appl. Microbiol. Biotechnol.
99
7399-7415
2015
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2
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1
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24
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24
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1
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738647
Fan
Site-directed mutagenesis swit ...
Aspergillus fumigatus
J. Biol. Chem.
290
1364-1373
2015
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1
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18
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1
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1
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18
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5
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1
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1
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739221
Fan
Tryptophan prenyltransferases ...
Aspergillus fumigatus
Org. Biomol. Chem.
13
7551-7557
2015
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2
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1
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1
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5
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1
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5
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1
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2
1
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2
2
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2
2
737837
Miyamoto
A 7-dimethylallyl tryptophan s ...
Aspergillus fumigatus
Bioorg. Med. Chem.
22
2517-2528
2014
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1
1
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5
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3
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1
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5
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1
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15
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1
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5
1
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1
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1
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5
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15
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1
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5
1
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3
3
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722461
Rudolf
Multisite prenylation of 4-sub ...
Claviceps purpurea
J. Am. Chem. Soc.
135
1895-1902
2013
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1
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2
5
1
1
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12
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2
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4
2
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3
4
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4
4
726466
Mahmoodi
-
Rearrangements in the mechanis ...
Aspergillus fumigatus
Pure Appl. Chem.
85
1935-1948
2013
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2
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721293
Schwarzer
Mimicking dimethylallyltryptop ...
Claviceps purpurea
Angew. Chem. Int. Ed. Engl.
51
11514-11516
2012
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723104
Yu
Prenyltransferases of the dime ...
Aspergillus fumigatus, Claviceps purpurea, Malbranchea aurantiaca
Methods Enzymol.
516
259-278
2012
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3
3
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3
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6
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3
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6
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1
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6
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3
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3
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3
3
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723326
Liebhold
Expansion of enzymatic Friedel ...
Aspergillus fumigatus
Org. Lett.
14
4882-4885
2012
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1
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721373
Yu
Substrate promiscuity of secon ...
Aspergillus fumigatus
Appl. Microbiol. Biotechnol.
92
737-748
2011
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722452
Luk
A cope rearrangement in the re ...
Aspergillus fumigatus
J. Am. Chem. Soc.
133
12342-12345
2011
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4
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