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Enzyme Nomenclature
Information on EC 4.1.2.42 - D-threonine aldolase
for references in articles please use BRENDA:EC4.1.2.42
Word Map on EC 4.1.2.42
- 4.1.2.42
- arthrobacter
- 5'-phosphate
- alcaligenes
-
low-specificity
-
d-specific
- xylosoxidans
-
erythro
-
alpha-position
-
beta-position
- l-threonine
-
plp-dependent
-
reinhardtii
-
pyridoxal-p
- medicine
-
chlamydomonas
-
dehydratase
- synthesis
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The enzyme appears in viruses and cellular organisms
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EC NUMBER 
COMMENTARY 
4.1.2.42
-
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RECOMMENDED NAME
GeneOntology No.
D-threonine aldolase
-
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REACTION
REACTION DIAGRAM
COMMENTARY
ORGANISM
UNIPROT
LITERATURE
D-allothreonine = glycine + acetaldehyde
-
-
-
-
D-threonine = glycine + acetaldehyde
-
-
-
-
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REACTION TYPE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
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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].
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CAS REGISTRY NUMBER
COMMENTARY
87588-22-5
-
9024-06-0
-
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ORGANISM
COMMENTARY
LITERATURE
UNIPROT
SEQUENCE DB
SOURCE
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SUBSTRATE
PRODUCT
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate)
(Substrate)
LITERATURE
(Substrate)
(Substrate)
COMMENTARY
(Product)
(Product)
LITERATURE
(Product)
(Product)
Reversibility
r=reversible
ir=irreversible
?=not specified
r=reversible
ir=irreversible
?=not specified
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
-
-
?
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
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-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-(4-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 + 3-hydroxybenzaldehyde
(2R,3S)-2-amino-3-hydroxy-3-(3-hydroxyphenyl)propanoic acid + (2R,3R)-2-amino-3-hydroxy-3-(4-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 + 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-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 + benzaldehyde
(2R,3S)-2-amino-3-hydroxy-3-phenylpropanoic acid + (2R,3R)-2-amino-3-hydroxy-3-phenylpropanoic acid
-
-
-
-
r
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
D-beta-hydroxy-alpha-aminovaleric acid
glycine + propionaldehyde
-
-
-
-
?
D-threonine
glycine + acetaldehyde
-
stereospecific for D-beta-hydroxyamino acids
-
?
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
?
-
-
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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NATURAL SUBSTRATES
NATURAL PRODUCTS
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate)
(Substrate)
LITERATURE
(Substrate)
(Substrate)
COMMENTARY
(Product)
(Product)
LITERATURE
(Product)
(Product)
REVERSIBILITY
r=reversible
ir=irreversible
?=not specified
r=reversible
ir=irreversible
?=not specified
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COFACTOR
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
pyridoxal 5'-phosphate
binds 1 mol of pyridoxal 5'-phosphate per mol of subunit, Lys59 is the cofactor binding site
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METALS and IONS
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
Co2+
Mg2+
Mn2+
additional information
-
Mg2+ ions show no effect on both selectivity and activity
Mn2+
-
requirement for a divalent cation, binds 1 mol Mn2+ per mol of subunit
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INHIBITORS
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
additional information
-
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
LITERATURE
IMAGE
1.8
DL-threo-beta-(3,4-methylenedioxyphenylserine)
pH 8.0, 30°C, with Mn2+; pH 8.0, 30°C, without Mn2+
2
DL-erythro-beta-(3,4-methylenedioxyphenylserine)
pH 8.0, 30°C, without Mn2+
2.5
DL-erythro-beta-(3,4-methylenedioxyphenylserine)
pH 8.0, 30°C, with Mn2+
1.2
DL-threo-beta-(3,4-dihydroxyphenylserine)
pH 8.0, 30°C, with Mn2+
1.4
DL-threo-beta-(3,4-dihydroxyphenylserine)
pH 8.0, 30°C, without Mn2+
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SPECIFIC ACTIVITY [µmol/min/mg]
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
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pH OPTIMUM
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
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pH RANGE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
6.5 - 9.5
-
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
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TEMPERATURE OPTIMUM
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
50
-
temperature-optimum for yield, but less diastereoselectivity, origin thermophilic organism
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TEMPERATURE RANGE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
30 - 50
-
only this range tested, at constant pH half of maximum yield achieved at 30°C, but 97% diastereoselectivity, at constant pH maximum yield achieved at 50°C, 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 40°C. Lowering the temperature to 5°C results in an increase of diastereoselectivity (up to 98%) as well as in a higher analytical yield (79%) after 4 h
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PDB
SCOP
CATH
ORGANISM
UNIPROT
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MOLECULAR WEIGHT
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
40000
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SUBUNITS
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
monomer
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TEMPERATURE STABILITY
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
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Purification/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
recombinant
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Cloned/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
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ENGINEERING
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
alrY265A
-
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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APPLICATION
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
medicine
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
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
-
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
-
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LINKS TO OTHER DATABASES (specific for EC-Number 4.1.2.42)
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