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2-bromobenzaldehyde + glycine
D-2-bromophenylserine
-
analytical yield: 6%, de: 35%, conditions: 1 ml solution containing glycine (1 M), benzaldehyde (or its derivate) (100 mM), pyridoxal 5'-phosphate (50 mM), MnCl2 (50 mM), and D-threonine aldolase (23 U) at 5°C, 4 h, ee >99% (D) for all reactions
-
-
?
2-chlorobenzaldehyde + glycine
D-2-chlorophenylserine
-
analytical yield: 27%, de: 67%, conditions: 1 ml solution containing glycine (1 M), benzaldehyde (or its derivate) (100 mM), pyridoxal 5'-phosphate (50 mM), MnCl2 (50 mM), and D-threonine aldolase (23 U) at 5°C, 4 h, ee >99% (D) for all reactions
-
-
?
2-fluorobenzaldehyde + glycine
D-2-fluorophenylserine
-
analytical yield: 68%, de: 95%, conditions: 1 ml solution containing glycine (1 M), benzaldehyde (or its derivate) (100 mM), pyridoxal 5'-phosphate (50 mM), MnCl2 (50 mM), and D-threonine aldolase (23 U) at 5°C, 4 h, ee >99% (D) for all reactions
-
-
?
2-nitrobenzaldehyde + glycine
D-2-nitrophenylserine
-
analytical yield: 18%, de: 65%, conditions: 1 ml solution containing glycine (1 M), benzaldehyde (or its derivate) (100 mM), pyridoxal 5'-phosphate (50 mM), MnCl2 (50 mM), and D-threonine aldolase (23 U) at 5°C, 4 h, ee >99% (D) for all reactions
-
-
?
3,4-methylenedioxybenzaldehyde + glycine
D-3,4-methylenedioxyphenylserine
-
analytical yield: 16%, de: 46%, conditions: 1 ml solution containing glycine (1 M), benzaldehyde (or its derivate) (100 mM), pyridoxal 5'-phosphate (50 mM), MnCl2 (50 mM), and D-threonine aldolase (23 U) at 5°C, 4 h, ee >99% (D) for all reactions
-
-
?
3-bromobenzaldehyde + glycine
D-3-bromophenylserine
-
analytical yield: 43%, de: 71%, conditions: 1 ml solution containing glycine (1 M), benzaldehyde (or its derivate) (100 mM), pyridoxal 5'-phosphate (50 mM), MnCl2 (50 mM), and D-threonine aldolase (23 U) at 5°C, 4 h, ee >99% (D) for all reactions
-
-
?
3-chlorobenzaldehyde + glycine
D-3-chlorophenylserine
-
analytical yield: 60%, de: 85%, conditions: 1 ml solution containing glycine (1 M), benzaldehyde (or its derivate) (100 mM), pyridoxal 5'-phosphate (50 mM), MnCl2 (50 mM), and D-threonine aldolase (23 U) at 5°C, 4 h, ee >99% (D) for all reactions
-
-
?
3-fluorobenzaldehyde + glycine
D-3-fluorophenylserine
-
analytical yield: 54%, de: 81%, conditions: 1 ml solution containing glycine (1 M), benzaldehyde (or its derivate) (100 mM), pyridoxal 5'-phosphate (50 mM), MnCl2 (50 mM), and D-threonine aldolase (23 U) at 5°C, 4 h, ee >99% (D) for all reactions
-
-
?
3-hydroxybenzaldehyde + glycine
D-3-hydroxyphenylserine
-
analytical yield: 76%, de: 86%, conditions: 1 ml solution containing glycine (1 M), benzaldehyde (or its derivate) (100 mM), pyridoxal 5'-phosphate (50 mM), MnCl2 (50 mM), and D-threonine aldolase (23 U) at 5°C, 4 h, ee >99% (D) for all reactions
-
-
?
3-nitrobenzaldehyde + glycine
D-3-nitrophenylserine
-
analytical yield: 90%, de: 80%, conditions: 1 ml solution containing glycine (1 M), benzaldehyde (or its derivate) (100 mM), pyridoxal 5'-phosphate (50 mM), MnCl2 (50 mM), and D-threonine aldolase (23 U) at 5°C, 4 h, ee >99% (D) for all reactions
-
-
?
4-(methylsulfonyl)benzaldehyde + glycine
D-3-(4-methylsulfonylphenyl)serine
-
analytical yield: 63%, de: 99%, conditions: 1 ml solution containing glycine (1 M), benzaldehyde (or its derivate) (100 mM), pyridoxal 5'-phosphate (50 mM), MnCl2 (50 mM), and D-threonine aldolase (23 U) at 5°C, 4 h, ee >99% (D) for all reactions
-
-
?
4-bromobenzaldehyde + glycine
D-4-bromophenylserine
-
analytical yield: 12%, de: 74%, conditions: 1 ml solution containing glycine (1 M), benzaldehyde (or its derivate) (100 mM), pyridoxal 5'-phosphate (50 mM), MnCl2 (50 mM), and D-threonine aldolase (23 U) at 5°C, 4 h, ee >99% (D) for all reactions
-
-
?
4-chlorobenzaldehyde + glycine
D-4-chlorophenylserine
-
analytical yield: 26%, de: 86%, conditions: 1 ml solution containing glycine (1 M), benzaldehyde (or its derivate) (100 mM), pyridoxal 5'-phosphate (50 mM), MnCl2 (50 mM), and D-threonine aldolase (23 U) at 5°C, 4 h, ee >99% (D) for all reactions
-
-
?
4-fluorobenzaldehyde + glycine
D-4-fluorophenylserine
-
analytical yield: 42%, de: 91%, conditions: 1 ml solution containing glycine (1 M), benzaldehyde (or its derivate) (100 mM), pyridoxal 5'-phosphate (50 mM), MnCl2 (50 mM), and D-threonine aldolase (23 U) at 5°C, 4 h, ee >99% (D) for all reactions
-
-
?
4-formylbenzenesulfonamide + glycine
D-2-amino-3-hydroxy-3-(4-sulfamoylphenyl)-propanoic acid
-
analytical yield: 53%, de: above 90%, conditions: 1 ml solution containing glycine (1 M), benzaldehyde (or its derivate) (100 mM), pyridoxal 5'-phosphate (50 mM), MnCl2 (50 mM), and D-threonine aldolase (23 U) at 5°C, 4 h, ee >99% (D) for all reactions
-
-
?
4-hydroxybenzaldehyde + glycine
D-4-hydroxyphenylserine
-
analytical yield: 15%, de: 70%, conditions: 1 ml solution containing glycine (1 M), benzaldehyde (or its derivate) (100 mM), pyridoxal 5'-phosphate (50 mM), MnCl2 (50 mM), and D-threonine aldolase (23 U) at 5°C, 4 h, ee >99% (D) for all reactions
-
-
?
4-nitrobenzaldehyde + glycine
D-4-nitrophenylserine
-
analytical yield: 31%, de: 75%, conditions: 1 ml solution containing glycine (1 M), benzaldehyde (or its derivate) (100 mM), pyridoxal 5'-phosphate (50 mM), MnCl2 (50 mM), and D-threonine aldolase (23 U) at 5°C, 4 h, ee >99% (D) for all reactions
-
-
?
alpha-methyl-beta-phenylserine
D-alanine + benzaldehyde
-
-
-
-
?
benzaldehyde + glycine
D-phenylserine
-
analytical yield: 79%, de: 98%, conditions: 1 ml solution containing glycine (1 M), benzaldehyde (or its derivate) (100 mM), pyridoxal 5'-phosphate (50 mM), MnCl2 (50 mM), and D-threonine aldolase (23 U) at 5°C, 4 h, ee >99% (D) for all reactions
-
-
?
D-alanine + 3-nitrobenzaldehyde
(betaS)-beta-hydroxy-alpha-methyl-3-nitro-D-phenylalanine
-
high concentrations of both substrates and 10fold excess of D-alanine over 3-nitrobenzaldehyde, 3 hours test time give less than 5% yield and 80% D-isomer, 24 hours test time give less than 12% yield and 65% D-isomer
-
-
r
D-alanine + 3-nitrobenzaldehyde
beta-(3-nitrophenyl)-alpha-methyl-serine
-
-
-
-
?
D-alanine + benzaldehyde
2-amino-3-hydroxy-2-methyl-3-phenylpropanoic acid
-
-
-
-
?
D-alanine + hexanal
2-amino-3-hydroxy-2-methyloctanoate
-
-
-
-
?
D-allo-threonine
glycine + acetaldehyde
D-beta-3,4-dihydroxyphenylserine
?
D-beta-3,4-methylenedioxyphenylserine
?
D-beta-hydroxy-alpha-aminovaleric acid
glycine + propionaldehyde
D-beta-phenylserine
glycine + benzaldehyde
D-serine + 3-nitrobenzaldehyde
beta-(3-nitrophenyl)-alpha-hydroxymethyl-serine
-
-
-
-
?
D-serine + benzaldehyde
2-amino-3-hydroxy-2-hydroxymethyl-3-phenylpropanoic acid
-
-
-
-
?
D-threo-phenylserine
benzaldehyde + glycine
-
-
-
r
D-threonine
glycine + acetaldehyde
DL-erythro-beta-(3,4-methylenedioxyphenylserine)
?
DL-erythro-phenylserine
glycine + benzaldehyde
DL-threo-beta-(3,4-dihydroxyphenylserine)
?
DL-threo-beta-(3,4-methylenedioxyphenylserine)
?
-
-
-
r
DL-threo-phenylserine
glycine + benzaldehyde
-
-
-
r
glycine + (4R)-2,2-dimethyl-1,3-dioxolane-4-carbaldehyde
(2R,3R)-2-amino-3-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]-3-hydroxypropanoic acid + (2R,3S)-2-amino-3-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]-3-hydroxypropanoic acid
-
-
-
-
r
glycine + (4S)-2,2-dimethyl-1,3-dioxolane-4-carbaldehyde
(2R,3R)-2-amino-3-[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]-3-hydroxypropanoic acid + (2R,3S)-2-amino-3-[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]-3-hydroxypropanoic acid
-
-
-
-
?
glycine + 2-aminobenzaldehyde
(betaS)-2-amino-beta-hydroxy-D-phenylalanine
-
high concentrations of both substrates and 10fold excess of glycine over benzaldehyde, 3 hours test time give less than 1% yield and no data about D-isomer, 24 hours test time give less than 1% yield and no data about D-isomer
-
-
r
glycine + 2-chlorobenzaldehyde
D-3-(2-chlorophenyl)serine
glycine + 2-fluorobenzaldehyde
D-3-(2-fluorophenyl)serine
the reaction conversion and the diastereomeric excess of the 2-substituted substrates decrease in the order of F, H, Cl, Br
-
-
r
glycine + 2-methylpropanal
(2R,3S)-2-amino-3-hydroxy-4-methylpentanoic acid + (2R,3R)-2-amino-3-hydroxy-4-methylpentanoic acid
-
-
-
-
r
glycine + 2-nitrobenzaldehyde
(2R,3S)-2-amino-3-hydroxy-3-(2-nitrophenyl)propanoic acid + (2R,3R)-2-amino-3-hydroxy-3-(2-nitrophenyl)propanoic acid
-
-
-
-
r
glycine + 2-nitrobenzaldehyde
(betaS)-beta-hydroxy-2-nitro-D-phenylalanine
-
high concentrations of both substrates and 10fold excess of glycine over 2-nitrobenzaldehyde, 3 hours test time give 1% yield and no data about D-isomer, 24 hours test time give 1% yield and more than 97% D-isomer
-
-
r
glycine + 2-nitrobenzaldehyde
D-3-(2-nitrophenyl)serine
the reaction conversion and the diastereomeric excess of the 2-substituted substrates decrease in the order of F, H, Cl, Br
-
-
r
glycine + 3-chlorobenzaldehyde
D-3-(3-chlorophenyl)serine
-
-
-
r
glycine + 3-fluorobenzaldehyde
D-3-(3-fluorophenyl)serine
-
-
-
r
glycine + 3-hydroxybenzaldehyde
(2R,3S)-2-amino-3-hydroxy-3-(3-hydroxyphenyl)propanoic acid + (2R,3R)-2-amino-3-hydroxy-3-(3-nitrophenyl)propanoic acid
-
-
-
-
r
glycine + 3-hydroxybenzaldehyde
(betaS)-beta,3-dihydroxy-D-phenylalanine
-
high concentrations of both substrates and 10fold excess of glycine over 3-hydroxybenzaldehyde, 3 hours test time give less than 1% yield, 24 hours test time give 3% yield and 70% D-isomer
-
-
r
glycine + 3-nitrobenzaldehyde
(betaS)-beta-hydroxy-3-nitro-D-phenylalanine
-
high concentrations of both substrates and 10fold excess of glycine over 3-nitrobenzaldehyde, 3 hours test time give 20% yield and 93% D-isomer, 24 hours test time give 55% yield and 85% D-isomer
-
-
r
glycine + 3-nitrobenzaldehyde
D-3-(3-nitrophenyl)serine
-
-
-
r
glycine + 4-(methylsulfonyl)benzaldehyde
D-3-(4-methylsulfonylphenyl)serine
-
-
-
r
glycine + 4-fluoro-3-nitrobenzaldehyde
(2R,3S)-2-amino-3-(4-fluoro-3-nitrophenyl)-3-hydroxypropanoic acid + (2R,3R)-2-amino-3-(4-fluoro-3-nitrophenyl)-3-hydroxypropanoic acid
-
-
-
-
r
glycine + 4-fluorobenzaldehyde
D-3-(4-fluorophenyl)serine
-
-
-
r
glycine + 4-methylbenzaldehyde
(2R,3S)-2-amino-3-hydroxy-3-(4-methylphenyl)propanoic acid + (2R,3R)-2-amino-3-hydroxy-3-(4-nitrophenyl)propanoic acid
-
-
-
-
r
glycine + 4-nitrobenzaldehyde
(2R,3S)-2-amino-3-hydroxy-3-(4-nitrophenyl)propanoic acid + (2R,3R)-2-amino-3-hydroxy-3-(4-nitrophenyl)propanoic acid
-
-
-
-
r
glycine + 4-nitrobenzaldehyde
(betaS)-beta-hydroxy-4-nitro-D-phenylalanine
-
high concentrations of both substrates and 10fold excess of glycine over 4-nitrobenzaldehyde, 3 hours test time give 12% yield and 40% D-isomer, 24 hours test time give 36% yield and 40% D-isomer
-
-
r
glycine + 4-nitrobenzaldehyde
D-3-(4-nitrophenyl)serine
-
-
-
r
glycine + acetaldehyde
D-allothreonine
glycine + acetaldehyde
D-threonine
glycine + acetaldehyde
D-threonine + D-allo-threonine
glycine + benzaldehyde
(2R,3S)-2-amino-3-hydroxy-3-phenylpropanoic acid + (2R,3R)-2-amino-3-hydroxy-3-phenylpropanoic acid
glycine + benzaldehyde
(betaS)-beta-hydroxy-D-phenylalanine
-
high concentrations of both substrates and 10fold excess of glycine over benzaldehyde, 3 hours test time give 10% yield and 97% D-isomer, 24 hours test time give 17% yield and 76% D-isomer
-
-
r
glycine + butyraldehyde
(2R,3S)-2-amino-3-hydroxyhexanoic acid + (2R,3R)-2-amino-3-hydroxyhexanoic acid
-
-
-
-
r
glycine + hexanaldehyde
(2R,3R)-2-amino-3-hydroxyoctanoic acid + (2R,3S)-2-amino-3-hydroxyoctanoic acid
-
-
-
-
r
glycine + octanaldehyde
(2R,3R)-2-amino-3-hydroxydecanoic acid + (2R,3S)-2-amino-3-hydroxydecanoic acid
-
-
-
-
r
glycine + phenylacetaldehyde
(2R,3S)-2-amino-3-hydroxy-4-phenylbutanoic acid + (2R,3R)-2-amino-3-hydroxy-4-phenylbutanoic acid
-
-
-
-
r
glycine + piperonal
(3S)-3-(1,3-benzodioxol-5-yl)-D-serine
-
high concentrations of both substrates and 10fold excess of glycine over piperonal, 3 hours test time give less than 1% yield and no data about D-isomer, 24 hours test time give 5% yield and 70% D-isomer
-
-
r
glycine + pyridine-4-carboxaldehyde
(2R,3S)-2-amino-3-hydroxy-3-(pyridin-4-yl)-propanoic acid
additional information
?
-
D-allo-threonine

glycine + acetaldehyde
-
-
-
-
r
D-allo-threonine
glycine + acetaldehyde
-
-
-
r
D-allo-threonine
glycine + acetaldehyde
-
-
-
-
r
D-allo-threonine
glycine + acetaldehyde
-
-
-
r
D-allo-threonine
glycine + acetaldehyde
-
-
-
r
D-allo-threonine
glycine + acetaldehyde
-
-
-
?
D-allo-threonine
glycine + acetaldehyde
-
-
-
?
D-allo-threonine
glycine + acetaldehyde
-
-
-
-
r
D-beta-3,4-dihydroxyphenylserine

?
-
-
-
-
?
D-beta-3,4-dihydroxyphenylserine
?
-
-
-
-
?
D-beta-3,4-methylenedioxyphenylserine

?
-
-
-
-
?
D-beta-3,4-methylenedioxyphenylserine
?
-
-
-
-
?
D-beta-hydroxy-alpha-aminovaleric acid

glycine + propionaldehyde
-
-
-
-
?
D-beta-hydroxy-alpha-aminovaleric acid
glycine + propionaldehyde
-
-
-
-
?
D-beta-phenylserine

glycine + benzaldehyde
-
-
-
-
?
D-beta-phenylserine
glycine + benzaldehyde
-
-
-
-
?
D-threonine

glycine + acetaldehyde
-
-
-
?, r
D-threonine
glycine + acetaldehyde
-
-
-
?
D-threonine
glycine + acetaldehyde
-
-
-
?, r
D-threonine
glycine + acetaldehyde
-
-
-
-
r
D-threonine
glycine + acetaldehyde
-
-
-
r
D-threonine
glycine + acetaldehyde
-
stereospecific for D-beta-hydroxyamino acids
-
?
D-threonine
glycine + acetaldehyde
-
-
-
-
r
D-threonine
glycine + acetaldehyde
-
-
-
?, r
D-threonine
glycine + acetaldehyde
-
-
-
r
D-threonine
glycine + acetaldehyde
-
-
-
r
D-threonine
glycine + acetaldehyde
-
-
-
-
r
D-threonine
glycine + acetaldehyde
-
-
-
r
D-threonine
glycine + acetaldehyde
-
-
-
r
D-threonine
glycine + acetaldehyde
-
-
-
-
?
D-threonine
glycine + acetaldehyde
-
-
-
-
r
DL-erythro-beta-(3,4-methylenedioxyphenylserine)

?
-
-
-
r
DL-erythro-beta-(3,4-methylenedioxyphenylserine)
?
-
-
-
r
DL-erythro-phenylserine

glycine + benzaldehyde
-
-
-
r
DL-erythro-phenylserine
glycine + benzaldehyde
-
-
-
r
DL-threo-beta-(3,4-dihydroxyphenylserine)

?
-
-
-
r
DL-threo-beta-(3,4-dihydroxyphenylserine)
?
-
-
-
r
glycine + 2-chlorobenzaldehyde

D-3-(2-chlorophenyl)serine
the reaction conversion and the diastereomeric excess of the 2-substituted substrates decrease in the order of F, H, Cl, Br
-
-
r
glycine + 2-chlorobenzaldehyde
D-3-(2-chlorophenyl)serine
the reaction conversion and the diastereomeric excess of the 2-substituted substrates decrease in the order of F, H, Cl, Br
-
-
r
glycine + acetaldehyde

D-allothreonine
the enzyme catalyzes the synthesis of D- and D-allothreonine from a mixture of glycine and acetaldehyde. The diastereomer excess of D-threonine is 18%
-
-
r
glycine + acetaldehyde
D-allothreonine
-
-
-
r
glycine + acetaldehyde

D-threonine
-
-
-
r
glycine + acetaldehyde
D-threonine
the enzyme catalyzes the synthesis of D- and D-allothreonine from a mixture of glycine and acetaldehyde. The diastereomer excess of D-threonine is 18%
-
-
r
glycine + acetaldehyde
D-threonine
-
-
-
r
glycine + acetaldehyde

D-threonine + D-allo-threonine
-
-
-
-
r
glycine + acetaldehyde
D-threonine + D-allo-threonine
-
-
-
r
glycine + acetaldehyde
D-threonine + D-allo-threonine
-
-
-
-
r
glycine + benzaldehyde

(2R,3S)-2-amino-3-hydroxy-3-phenylpropanoic acid + (2R,3R)-2-amino-3-hydroxy-3-phenylpropanoic acid
the erythro isomer is obtained as the major product when the temperature is above 15°C, and lowering the temperature result in an increase in threo isomer.Water-miscible organic solvents exert limited effect on the conversion, but greatly enhance the diastereomeric excess of the product, with 10% CH3CN giving the highest diastereomeric excess. For other organic solvents (THF, ethyl acetate, 2-methoxy-2-methylpropan, 1,4-dioxane, dichloromethane and toluene), lower stereoselectivity at the beta-carbon is observed
-
-
r
glycine + benzaldehyde
(2R,3S)-2-amino-3-hydroxy-3-phenylpropanoic acid + (2R,3R)-2-amino-3-hydroxy-3-phenylpropanoic acid
the erythro isomer is obtained as the major product when the temperature is above 15°C, and lowering the temperature result in an increase in threo isomer.Water-miscible organic solvents exert limited effect on the conversion, but greatly enhance the diastereomeric excess of the product, with 10% CH3CN giving the highest diastereomeric excess. For other organic solvents (THF, ethyl acetate, 2-methoxy-2-methylpropan, 1,4-dioxane, dichloromethane and toluene), lower stereoselectivity at the beta-carbon is observed
-
-
r
glycine + benzaldehyde
(2R,3S)-2-amino-3-hydroxy-3-phenylpropanoic acid + (2R,3R)-2-amino-3-hydroxy-3-phenylpropanoic acid
-
-
-
-
r
glycine + pyridine-4-carboxaldehyde

(2R,3S)-2-amino-3-hydroxy-3-(pyridin-4-yl)-propanoic acid
-
-
-
?
glycine + pyridine-4-carboxaldehyde
(2R,3S)-2-amino-3-hydroxy-3-(pyridin-4-yl)-propanoic acid
-
-
-
?
glycine + pyridine-4-carboxaldehyde
(2R,3S)-2-amino-3-hydroxy-3-(pyridin-4-yl)-propanoic acid
-
-
-
?
glycine + pyridine-4-carboxaldehyde
(2R,3S)-2-amino-3-hydroxy-3-(pyridin-4-yl)-propanoic acid
-
-
-
?
additional information

?
-
-
a high excess of glycine shifts the equilibrium toward the phenylserine side and thus 10 equiv of glycine is utilized (1 M glycine, 100 mM benzaldehyde) throughout the entire study
-
-
?
additional information
?
-
-
in a systematic study, 21 ring-substituted benzaldehydes are reacted with glycine under catalysis with a L-threonine aldolase (LTA) from Pseudomonas putida and a D-threonine aldolase (DTA) from Alcaligenes xylosoxidans to form the corresponding beta-hydroxy-alpha-amino acids
-
-
?
additional information
?
-
the enzyme shows high activity toward aromatic aldehydes with electron-withdrawing substituents. The substrate profiling indicates that the enzyme accepts a wider range of acceptor substrates and is more active toward aromatic aldehydes bearing electron-withdrawing groups than those with electron-donating substituents. Molecular docking studies suggest that the substituent on the benzene ring of the substrate is critical in determining the enzyme activity and stereoselectivity by affecting the interaction between the beta-OH-group of the substrate and the manganese ion
-
-
?
additional information
?
-
the enzyme shows high activity toward aromatic aldehydes with electron-withdrawing substituents. The substrate profiling indicates that the enzyme accepts a wider range of acceptor substrates and is more active toward aromatic aldehydes bearing electron-withdrawing groups than those with electron-donating substituents. Molecular docking studies suggest that the substituent on the benzene ring of the substrate is critical in determining the enzyme activity and stereoselectivity by affecting the interaction between the beta-OH-group of the substrate and the manganese ion
-
-
?
additional information
?
-
-
no aldol condensation of glycine with n-pentanal or 2-methylpropanal
-
-
?
additional information
?
-
-
no activity with but-2-enal, 4-hydroxybenzaldehyde
-
-
?
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