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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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medicine
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efficient biocatalyst for resolution of L-X-3,4-methylenedioxyphenylserine, an intermediate for production of a therapeutic drug for Parkinson's disease
medicine
-
low-specificity threonine aldolase can be used in production of L-threo-3-[4-(methylthio)phenylserine], an intermediate for synthesis of antibiotics florfenicol and thiamphenicol
medicine
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low-specificity threonine aldolase can be used in production of L-threo-3-[4-(methylthio)phenylserine], an intermediate for synthesis of antibiotics florfenicol and thiamphenicol
-
pharmacology
efficient, environmentally friendly process for the production of (2R,3S)-2-amino-3-hydroxy-3-(pyridin-4-yl)-propanoic acid by a recombinant D-threonine aldolase catalyzed aldol addition of glycine and pyridine 4-carboxaldehyde. (2R,3S)-2-amino-3-hydroxy-3-(pyridin-4-yl)-propanoic acid, is a key intermediate in the synthesis of the (2R,3S)-2-amino-3-hydroxy-3-(pyridin-4-yl)-1-(pyrrolidin-1-yl)propan-1-one, a developmental drug candidate. The aldol addition product directly crystallizes out from the reaction mixture in high purity and high diastereo- and enantioselectivity, contributing to high yield and allowing easy isolation, processing, and downstream utilization
pharmacology
efficient, environmentally friendly process for the production of (2R,3S)-2-amino-3-hydroxy-3-(pyridin-4-yl)-propanoic acid by a recombinant D-threonine aldolase catalyzed aldol addition of glycine and pyridine 4-carboxaldehyde. (2R,3S)-2-amino-3-hydroxy-3-(pyridin-4-yl)-propanoic acid, is a key intermediate in the synthesis of the (2R,3S)-2-amino-3-hydroxy-3-(pyridin-4-yl)-1-(pyrrolidin-1-yl)propan-1-one, a developmental drug candidate. The aldol addition product directly crystallizes out from the reaction mixture in high purity and high diastereo- and enantioselectivity, contributing to high yield and allowing easy isolation, processing, and downstream utilization
pharmacology
the enzyme has a considerable potential in biocatalysis for the stereospecific synthesis of various beta-hydroxy amino acids, which are valuable building blocks for the production of pharmaceuticals
pharmacology
-
efficient, environmentally friendly process for the production of (2R,3S)-2-amino-3-hydroxy-3-(pyridin-4-yl)-propanoic acid by a recombinant D-threonine aldolase catalyzed aldol addition of glycine and pyridine 4-carboxaldehyde. (2R,3S)-2-amino-3-hydroxy-3-(pyridin-4-yl)-propanoic acid, is a key intermediate in the synthesis of the (2R,3S)-2-amino-3-hydroxy-3-(pyridin-4-yl)-1-(pyrrolidin-1-yl)propan-1-one, a developmental drug candidate. The aldol addition product directly crystallizes out from the reaction mixture in high purity and high diastereo- and enantioselectivity, contributing to high yield and allowing easy isolation, processing, and downstream utilization
-
pharmacology
-
efficient, environmentally friendly process for the production of (2R,3S)-2-amino-3-hydroxy-3-(pyridin-4-yl)-propanoic acid by a recombinant D-threonine aldolase catalyzed aldol addition of glycine and pyridine 4-carboxaldehyde. (2R,3S)-2-amino-3-hydroxy-3-(pyridin-4-yl)-propanoic acid, is a key intermediate in the synthesis of the (2R,3S)-2-amino-3-hydroxy-3-(pyridin-4-yl)-1-(pyrrolidin-1-yl)propan-1-one, a developmental drug candidate. The aldol addition product directly crystallizes out from the reaction mixture in high purity and high diastereo- and enantioselectivity, contributing to high yield and allowing easy isolation, processing, and downstream utilization
-
synthesis
-
alanine racemase with engineered function of D-threonine aldolase, capable of synthesizing beta-hydroxy-alpha-amino acids, stereoselectivity is comparable to that of D-threonine aldolase
synthesis
efficient, environmentally friendly process for the production of (2R,3S)-2-amino-3-hydroxy-3-(pyridin-4-yl)-propanoic acid by a recombinant D-threonine aldolase catalyzed aldol addition of glycine and pyridine 4-carboxaldehyde. (2R,3S)-2-amino-3-hydroxy-3-(pyridin-4-yl)-propanoic acid, is a key intermediate in the synthesis of the (2R,3S)-2-amino-3-hydroxy-3-(pyridin-4-yl)-1-(pyrrolidin-1-yl)propan-1-one, a developmental drug candidate. The aldol addition product directly crystallizes out from the reaction mixture in high purity and high diastereo- and enantioselectivity, contributing to high yield and allowing easy isolation, processing, and downstream utilization
synthesis
efficient, environmentally friendly process for the production of (2R,3S)-2-amino-3-hydroxy-3-(pyridin-4-yl)-propanoic acid by a recombinant D-threonine aldolase catalyzed aldol addition of glycine and pyridine 4-carboxaldehyde. (2R,3S)-2-amino-3-hydroxy-3-(pyridin-4-yl)-propanoic acid, is a key intermediate in the synthesis of the (2R,3S)-2-amino-3-hydroxy-3-(pyridin-4-yl)-1-(pyrrolidin-1-yl)propan-1-one, a developmental drug candidate. The aldol addition product directly crystallizes out from the reaction mixture in high purity and high diastereo- and enantioselectivity, contributing to high yield and allowing easy isolation, processing, and downstream utilization
synthesis
-
the enzyme can be used for the asymmetric synthesis alpha-quaternary alpha-amino acids
synthesis
the enzyme has a considerable potential in biocatalysis for the stereospecific synthesis of various beta-hydroxy amino acids, which are valuable building blocks for the production of pharmaceuticals
synthesis
the enzyme is a powerful tool for the stereospecific synthesis of various beta-hydroxy amino acids in synthetic organic chemistry
synthesis
the enzyme might be a promising biocatalyst for producing chiral aromatic beta-hydroxy-alpha-amino acids
synthesis
-
the enzyme might be a promising biocatalyst for producing chiral aromatic beta-hydroxy-alpha-amino acids
-
synthesis
-
efficient, environmentally friendly process for the production of (2R,3S)-2-amino-3-hydroxy-3-(pyridin-4-yl)-propanoic acid by a recombinant D-threonine aldolase catalyzed aldol addition of glycine and pyridine 4-carboxaldehyde. (2R,3S)-2-amino-3-hydroxy-3-(pyridin-4-yl)-propanoic acid, is a key intermediate in the synthesis of the (2R,3S)-2-amino-3-hydroxy-3-(pyridin-4-yl)-1-(pyrrolidin-1-yl)propan-1-one, a developmental drug candidate. The aldol addition product directly crystallizes out from the reaction mixture in high purity and high diastereo- and enantioselectivity, contributing to high yield and allowing easy isolation, processing, and downstream utilization
-
synthesis
-
efficient, environmentally friendly process for the production of (2R,3S)-2-amino-3-hydroxy-3-(pyridin-4-yl)-propanoic acid by a recombinant D-threonine aldolase catalyzed aldol addition of glycine and pyridine 4-carboxaldehyde. (2R,3S)-2-amino-3-hydroxy-3-(pyridin-4-yl)-propanoic acid, is a key intermediate in the synthesis of the (2R,3S)-2-amino-3-hydroxy-3-(pyridin-4-yl)-1-(pyrrolidin-1-yl)propan-1-one, a developmental drug candidate. The aldol addition product directly crystallizes out from the reaction mixture in high purity and high diastereo- and enantioselectivity, contributing to high yield and allowing easy isolation, processing, and downstream utilization
-
Please wait a moment until the data is sorted. This message will disappear when the data is sorted.
Liu, J.Q.; Odani, M.; Dairi, T.; Itoh, N.; Shimizu, S.; Yamada, H.
A new route to L-threo-3-[4-(methylthio)phenylserine], a key intermediate for the synthesis of antibiotics: recombinant low-specificity D-threonine aldolase-catalyzed stereospecific resolution
Appl. Microbiol. Biotechnol.
51
586-591
1999
Arthrobacter sp., Arthrobacter sp. DK-38
brenda
Liu, J.Q.; Odani, M.; Yasuoka, T.; Dairi, T.; Itoh, N.; Kataoka, M.; Shimizu, S.; Yamada, H.
Gene cloning and overproduction of low-specificity D-threonine aldolase from Alcaligenes xylosoxidans and its application for production of a key intermediate for parkinsonism drug
Appl. Microbiol. Biotechnol.
54
44-51
2000
Achromobacter xylosoxidans
brenda
Paiardini, A.; Contestabile, R.; D'Aguanno, S.; Pascarella, S.; Bossa, F.
Threonine aldolase and alanine racemase: novel examples of convergent evolution in the superfamily of vitamin B6-dependent enzymes
Biochim. Biophys. Acta
1647
214-219
2003
Arthrobacter sp.
brenda
Liu, J.Q.; Dairi, T.; Itoh, N.; Kataoka, M.; Shimizu, S.; Yamada, H.
Diversity of microbial threonine aldolases and their application
J. Mol. Catal. B
10
107-115
2000
Arthrobacter sp., Arthrobacter sp. DK-38
-
brenda
Kataoka, M.; Ikemi, M.; Morikawa, T.; Miyoshi, T.; Nishi, K.I.; Wada, M.; Yamada, H.; Shimizu, S.
Isolation and characterization of D-threonine aldolase, a pyridoxal-5'-phosphate-dependent enzyme from Arthrobacter sp. DK-38
Eur. J. Biochem.
248
385-393
1997
Arthrobacter sp., Arthrobacter sp. DK-38
brenda
Kimura, T.; Vassilev, V.P.; Shen, G.J.; Wong, C.H.
Enzymic synthesis of beta-hydroxy-alpha-amino acids based on recombinant D- and L-threonine aldolases
J. Am. Chem. Soc.
119
11734-11742
1997
Xanthomonas oryzae
-
brenda
Liu, J.Q.; Dairi, T.; Itoh, N.; Kataoka, M.; Shimizu, S.; Yamada, H.
A novel metal-activated pyridoxal enzyme with a unique primary structure, low specificity D-threonine aldolase from Arthrobacter sp. strain DK-38. Molecular cloning and cofactor characterization
J. Biol. Chem.
273
16678-16685
1998
Arthrobacter sp. (O82872), Arthrobacter sp., Arthrobacter sp. DK-38 (O82872)
brenda
Steinreiber, J.; Fesko, K.; Reisinger, C.; Schuermann, M.; van Assema, F.; Wolberg, M.; Mink, D.; Griengl, H.
Threonine aldolases-an emerging tool for organic synthesis
Tetrahedron
63
918-926
2006
Achromobacter xylosoxidans
-
brenda
Fesko, K.; Giger, L.; Hilvert, D.
Synthesis of beta-hydroxy-alpha-amino acids with a reengineered alanine racemase
Bioorg. Med. Chem. Lett.
18
5987-5990
2008
Geobacillus stearothermophilus
brenda
Hirato, Y.; Goto, M.; Tokuhisa, M.; Tanigawa, M.; Nishimura, K.
Crystallization and X-ray analysis of D-threonine aldolase from Chlamydomonas reinhardtii
Acta Crystallogr. Sect. F
73
86-89
2017
Chlamydomonas reinhardtii (A0A1C9ZZ39), Chlamydomonas reinhardtii
brenda
Fesko, K.; Strohmeier, G.A.; Breinbauer, R.
Expanding the threonine aldolase toolbox for the asymmetric synthesis of tertiary alpha-amino acids
Appl. Microbiol. Biotechnol.
99
9651-9661
2015
Pseudomonas sp.
brenda
Chen, Q.; Chen, X.; Cui, Y.; Ren, J.; Lu, W.; Feng, J.; Wu, Q.; Zhu, D.
A new D-threonine aldolase as a promising biocatalyst for highly stereoselective preparation of chiral aromatic beta-hydroxy-alpha-amino acids
Catal. Sci. Technol.
7
5964-5973
2017
Delftia sp. (A0A031HCH9), Delftia sp. RIT313 (A0A031HCH9)
-
brenda
Blesl, J.; Trobe, M.; Anderl, F.; Breinbauer, R.; Strohmeier, G.; Fesko, K.
Application of threonine aldolases for the asymmetric synthesis alpha-quaternary alpha-amino acids
ChemCatChem
53
1-7
2018
Pseudomonas sp.
-
brenda
Goldberg, S.; Goswami, A.; Guo, Z.; Chan, Y.; Lo, E.; Lee, A.; Truc, V.; Natalie, K.; Hang, C.; Rossano, L.; Schmidt, M.
Preparation of beta-hydroxy-alpha-amino acid using recombinant beta-threonine aldolase
Org. Process Res. Dev.
19
1308-1316
2015
Arthrobacter sp. (O82872), Achromobacter xylosoxidans (Q9RBG6), Arthrobacter sp. DK-38 (O82872), Achromobacter xylosoxidans IFO 12699 (Q9RBG6)
-
brenda
Hirato, Y.; Tokuhisa, M.; Tanigawa, M.; Ashida, H.; Tanaka, H.; Nishimura, K.
Cloning and characterization of D-threonine aldolase from the green alga Chlamydomonas reinhardtii
Phytochemistry
135
18-23
2017
Chlamydomonas reinhardtii (A0A1C9ZZ39), Chlamydomonas reinhardtii
brenda
Uhl, M.K.; Oberdorfer, G.; Steinkellner, G.; Riegler-Berket, L.; Mink, D.; van Assema, F.; Schuermann, M.; Gruber, K.
The crystal structure of D-threonine aldolase from Alcaligenes xylosoxidans provides insight into a metal ion assisted PLP-dependent mechanism
PLoS ONE
10
e0124056
2015
Achromobacter xylosoxidans (A0A0J9X243), Achromobacter xylosoxidans
brenda