Information on EC 4.1.2.42 - D-threonine aldolase

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The enzyme appears in viruses and cellular organisms

EC NUMBER
COMMENTARY hide
4.1.2.42
-
RECOMMENDED NAME
GeneOntology No.
D-threonine aldolase
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REACTION
REACTION DIAGRAM
COMMENTARY hide
ORGANISM
UNIPROT
LITERATURE
D-allothreonine = glycine + acetaldehyde
show the reaction diagram
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-
-
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D-threonine = glycine + acetaldehyde
show the reaction diagram
REACTION TYPE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
aldol condensation
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SYSTEMATIC NAME
IUBMB Comments
D-threonine acetaldehyde-lyase (glycine-forming)
A pyridoxal-phosphate protein that is activated by divalent metal cations (e.g. Co2+, Ni2+, Mn2+ or Mg2+) [1,2]. The reaction is reversible, which can lead to the interconversion of D-threonine and D-allothreonine [1]. Several other D-beta-hydroxy-alpha-amino acids, such as D-beta-phenylserine, D-beta-hydroxy-alpha-aminovaleric acid and D-beta-3,4-dihydroxyphenylserine, can also act as substrate [1].
CAS REGISTRY NUMBER
COMMENTARY hide
87588-22-5
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9024-06-0
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SUBSTRATE
PRODUCT                       
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate) hide
LITERATURE
(Substrate)
COMMENTARY
(Product) hide
LITERATURE
(Product)
Reversibility
r=reversible
ir=irreversible
?=not specified
2-bromobenzaldehyde + glycine
D-2-bromophenylserine
show the reaction diagram
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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 5C, 4 h, ee >99% (D) for all reactions
-
-
?
2-chlorobenzaldehyde + glycine
D-2-chlorophenylserine
show the reaction diagram
-
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 5C, 4 h, ee >99% (D) for all reactions
-
-
?
2-fluorobenzaldehyde + glycine
D-2-fluorophenylserine
show the reaction diagram
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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 5C, 4 h, ee >99% (D) for all reactions
-
-
?
2-nitrobenzaldehyde + glycine
D-2-nitrophenylserine
show the reaction diagram
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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 5C, 4 h, ee >99% (D) for all reactions
-
-
?
3,4-methylenedioxybenzaldehyde + glycine
D-3,4-methylenedioxyphenylserine
show the reaction diagram
-
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 5C, 4 h, ee >99% (D) for all reactions
-
-
?
3-bromobenzaldehyde + glycine
D-3-bromophenylserine
show the reaction diagram
-
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 5C, 4 h, ee >99% (D) for all reactions
-
-
?
3-chlorobenzaldehyde + glycine
D-3-chlorophenylserine
show the reaction diagram
-
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 5C, 4 h, ee >99% (D) for all reactions
-
-
?
3-fluorobenzaldehyde + glycine
D-3-fluorophenylserine
show the reaction diagram
-
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 5C, 4 h, ee >99% (D) for all reactions
-
-
?
3-hydroxybenzaldehyde + glycine
D-3-hydroxyphenylserine
show the reaction diagram
-
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 5C, 4 h, ee >99% (D) for all reactions
-
-
?
3-nitrobenzaldehyde + glycine
D-3-nitrophenylserine
show the reaction diagram
-
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 5C, 4 h, ee >99% (D) for all reactions
-
-
?
4-(methylsulfonyl)benzaldehyde + glycine
D-3-(4-methylsulfonylphenyl)serine
show the reaction diagram
-
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 5C, 4 h, ee >99% (D) for all reactions
-
-
?
4-bromobenzaldehyde + glycine
D-4-bromophenylserine
show the reaction diagram
-
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 5C, 4 h, ee >99% (D) for all reactions
-
-
?
4-chlorobenzaldehyde + glycine
D-4-chlorophenylserine
show the reaction diagram
-
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 5C, 4 h, ee >99% (D) for all reactions
-
-
?
4-fluorobenzaldehyde + glycine
D-4-fluorophenylserine
show the reaction diagram
-
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 5C, 4 h, ee >99% (D) for all reactions
-
-
?
4-formylbenzenesulfonamide + glycine
D-2-amino-3-hydroxy-3-(4-sulfamoylphenyl)-propanoic acid
show the reaction diagram
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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 5C, 4 h, ee >99% (D) for all reactions
-
-
?
4-hydroxybenzaldehyde + glycine
D-4-hydroxyphenylserine
show the reaction diagram
-
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 5C, 4 h, ee >99% (D) for all reactions
-
-
?
4-nitrobenzaldehyde + glycine
D-4-nitrophenylserine
show the reaction diagram
-
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 5C, 4 h, ee >99% (D) for all reactions
-
-
?
benzaldehyde + glycine
D-phenylserine
show the reaction diagram
-
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 5C, 4 h, ee >99% (D) for all reactions
-
-
?
D-alanine + 3-nitrobenzaldehyde
(betaS)-beta-hydroxy-alpha-methyl-3-nitro-D-phenylalanine
show the reaction diagram
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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
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r
D-allo-threonine
glycine + acetaldehyde
show the reaction diagram
D-beta-3,4-dihydroxyphenylserine
?
show the reaction diagram
D-beta-3,4-methylenedioxyphenylserine
?
show the reaction diagram
D-beta-hydroxy-alpha-aminovaleric acid
glycine + propionaldehyde
show the reaction diagram
D-beta-phenylserine
glycine + benzaldehyde
show the reaction diagram
-
-
-
-
?
D-threonine
glycine + acetaldehyde
show the reaction diagram
DL-erythro-beta-(3,4-methylenedioxyphenylserine)
?
show the reaction diagram
DL-erythro-phenylserine
glycine + benzaldehyde
show the reaction diagram
DL-threo-beta-(3,4-dihydroxyphenylserine)
?
show the reaction diagram
DL-threo-beta-(3,4-methylenedioxyphenylserine)
?
show the reaction diagram
-
-
-
r
DL-threo-phenylserine
glycine + benzaldehyde
show the reaction diagram
-
-
-
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
show the reaction diagram
-
-
-
-
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
show the reaction diagram
-
-
-
-
?
glycine + 2-aminobenzaldehyde
(betaS)-2-amino-beta-hydroxy-D-phenylalanine
show the reaction diagram
-
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-methylpropanal
(2R,3S)-2-amino-3-hydroxy-4-methylpentanoic acid + (2R,3R)-2-amino-3-hydroxy-4-methylpentanoic acid
show the reaction diagram
-
-
-
-
r
glycine + 2-nitrobenzaldehyde
(2R,3S)-2-amino-3-hydroxy-3-(2-nitrophenyl)propanoic acid + (2R,3R)-2-amino-3-hydroxy-3-(4-nitrophenyl)propanoic acid
show the reaction diagram
-
-
-
-
r
glycine + 2-nitrobenzaldehyde
(betaS)-beta-hydroxy-2-nitro-D-phenylalanine
show the reaction diagram
-
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
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r
glycine + 3-hydroxybenzaldehyde
(2R,3S)-2-amino-3-hydroxy-3-(3-hydroxyphenyl)propanoic acid + (2R,3R)-2-amino-3-hydroxy-3-(4-nitrophenyl)propanoic acid
show the reaction diagram
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-
-
-
r
glycine + 3-hydroxybenzaldehyde
(betaS)-beta,3-dihydroxy-D-phenylalanine
show the reaction diagram
-
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
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-
r
glycine + 3-nitrobenzaldehyde
(betaS)-beta-hydroxy-3-nitro-D-phenylalanine
show the reaction diagram
-
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
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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
show the reaction diagram
-
-
-
-
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
show the reaction diagram
-
-
-
-
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
show the reaction diagram
-
-
-
-
r
glycine + 4-nitrobenzaldehyde
(betaS)-beta-hydroxy-4-nitro-D-phenylalanine
show the reaction diagram
-
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
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r
glycine + acetaldehyde
D-threonine + D-allo-threonine
show the reaction diagram
glycine + benzaldehyde
(2R,3S)-2-amino-3-hydroxy-3-phenylpropanoic acid + (2R,3R)-2-amino-3-hydroxy-3-phenylpropanoic acid
show the reaction diagram
-
-
-
-
r
glycine + benzaldehyde
(betaS)-beta-hydroxy-D-phenylalanine
show the reaction diagram
-
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
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r
glycine + butyraldehyde
(2R,3S)-2-amino-3-hydroxyhexanoic acid + (2R,3R)-2-amino-3-hydroxyhexanoic acid
show the reaction diagram
-
-
-
-
r
glycine + hexanaldehyde
(2R,3R)-2-amino-3-hydroxyoctanoic acid + (2R,3S)-2-amino-3-hydroxyoctanoic acid
show the reaction diagram
-
-
-
-
r
glycine + octanaldehyde
(2R,3R)-2-amino-3-hydroxydecanoic acid + (2R,3S)-2-amino-3-hydroxydecanoic acid
show the reaction diagram
-
-
-
-
r
glycine + phenylacetaldehyde
(2R,3S)-2-amino-3-hydroxy-4-phenylbutanoic acid + (2R,3R)-2-amino-3-hydroxy-4-phenylbutanoic acid
show the reaction diagram
-
-
-
-
r
glycine + piperonal
(3S)-3-(1,3-benzodioxol-5-yl)-D-serine
show the reaction diagram
-
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
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-
r
additional information
?
-
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
D-threonine
glycine + acetaldehyde
show the reaction diagram
COFACTOR
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
pyridoxal 5'-phosphate
METALS and IONS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
Ni2+
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divalent cation required: Co2+, Ni2+, Mg2+ or Mn2+
additional information
-
Mg2+ ions show no effect on both selectivity and activity
INHIBITORS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
acetonitrile
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inactivates
dimethylformamide
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inactivates
additional information
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enzyme completely loses activity in absence of either pyridoxal 5'-phosphate or divalent cations
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KM VALUE [mM]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.99 - 14
D-allo-threonine
0.94 - 8.8
D-threonine
2 - 2.5
DL-erythro-beta-(3,4-methylenedioxyphenylserine)
4.9 - 5.3
DL-erythro-phenylserine
1.2 - 1.4
DL-threo-beta-(3,4-dihydroxyphenylserine)
1.8
DL-threo-beta-(3,4-methylenedioxyphenylserine)
pH 8.0, 30C, with Mn2+; pH 8.0, 30C, without Mn2+
5.4 - 5.9
DL-threo-phenylserine
SPECIFIC ACTIVITY [µmol/min/mg]
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
pH OPTIMUM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
7.5
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aldol addition
8
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cleavage reaction
9.5
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pH-optimum for yield, but less diastereoselectivity
pH RANGE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
6.5 - 9.5
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D-threonine aldolase shows little activity at pH 6.0. However, by increasing the pH to 9.5 the analytical yield of D-phenylserine is doubled retaining high diastereoselectivity as compared to pH 8.0
TEMPERATURE OPTIMUM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
50
-
temperature-optimum for yield, but less diastereoselectivity, origin thermophilic organism
TEMPERATURE RANGE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
30 - 50
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only this range tested, at constant pH half of maximum yield achieved at 30C, but 97% diastereoselectivity, at constant pH maximum yield achieved at 50C, but only 87% diastereoselectivity
additional information
-
for the synthesis of D-phenylserine employing D-threonine aldolase, the rate of the aldol reaction is studied from 5 to 40C. Lowering the temperature to 5C results in an increase of diastereoselectivity (up to 98%) as well as in a higher analytical yield (79%) after 4 h
LOCALIZATION
ORGANISM
UNIPROT
COMMENTARY hide
GeneOntology No.
LITERATURE
SOURCE
PDB
SCOP
CATH
ORGANISM
UNIPROT
Alcaligenes xylosoxydans xylosoxydans
MOLECULAR WEIGHT
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
SUBUNITS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
monomer
TEMPERATURE STABILITY
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
50
-
100% activity after 15 min
Purification/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
recombinant
Cloned/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
cloned in Escherichia coli
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expression in Escherichia coli
overexpression in Escherichia coli
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ENGINEERING
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
alrY265A
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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
APPLICATION
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
medicine
synthesis
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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
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