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Information on EC 4.1.2.48 - low-specificity L-threonine aldolase
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4.1.2.48 low-specificity L-threonine aldolaseIUBMB Comments
Requires pyridoxal phosphate. The low-specificity L-threonine aldolase can act on both L-threonine and L-allo-threonine [1,2]. The enzyme from Escherichia coli can also act on L-threo-phenylserine and L-erythro-phenylserine . The enzyme can also catalyse the aldol condensation of glycolaldehyde and glycine to form 4-hydroxy-L-threonine, an intermediate of pyridoxal phosphate biosynthesis . Different from EC 4.1.2.5, L-threonine aldolase, and EC 4.1.2.49, L-allo-threonine aldolase.
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Word Map
The expected taxonomic range for this enzyme is: Bacteria, Eukaryota, Archaea
Reaction Schemes
Synonyms
threonine aldolase, low-specificity l-threonine aldolase, serine hydroxy-methyl transferase, 
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SYNONYM 
ORGANISM
UNIPROT
COMMENTARY 
LITERATURE
L-TA
L-threonine aldolase
LtaE
LtaE
-
-
-
-
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REACTION
REACTION DIAGRAM
COMMENTARY
ORGANISM
UNIPROT
LITERATURE
L-allo-threonine = glycine + acetaldehyde
-
-
-
-
L-threonine = glycine + acetaldehyde
(1)
-
-
-
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PATHWAY SOURCE
PATHWAYS
KEGG
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SYSTEMATIC NAME
IUBMB Comments
L-threonine/L-allo-threonine acetaldehyde-lyase (glycine-forming)
Requires pyridoxal phosphate. The low-specificity L-threonine aldolase can act on both L-threonine and L-allo-threonine [1,2]. The enzyme from Escherichia coli can also act on L-threo-phenylserine and L-erythro-phenylserine [4]. The enzyme can also catalyse the aldol condensation of glycolaldehyde and glycine to form 4-hydroxy-L-threonine, an intermediate of pyridoxal phosphate biosynthesis [3]. Different from EC 4.1.2.5, L-threonine aldolase, and EC 4.1.2.49, L-allo-threonine aldolase.
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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
(R)-N-Cbz-alaninal + glycine
(2S,3R,4R)-2-amino-4-(benzyloxycarbonylamino)-3-hydroxypentanoic acid
(R)-N-Cbz-alaninal + glycine
(2S,3S,4R)-2-amino-4-(benzyloxycarbonylamino)-3-hydroxypentanoic acid
-
conversion: 40%, glycine concentration: 70 mM, reaction temperature: 4°C, yield: 30%, L-erythro/L-threo: 16:84
-
-
?
benzyloxyacetaldehyde + glycine
(2S,3S)-2-amino-4-(benzyloxy)-3-hydroxybutanoic acid
-
conversion: 45%, glycine concentration: 140 mM, reaction temperature: 25°C, yield: 30%, L-erythro/L-threo: 40:60
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-
?
DL-threo-(3-methylsulfonylphenyl)serine
glycine + 3-methylsulfonylbenzaldehyde
121% of the activity with L-threonine
-
-
?
DL-threo-(3-nitrophenyl)serine
glycine + 3-nitrobenzaldehyde
143% of the activity with L-threonine
-
-
?
glycine + 3,4-dihydroxybenzaldehyde
L-threo-3,4-dihydroxyphenylserine + L-erythro-3,4-dihydroxyphenylserine
glycine + glycolaldehyde
L-4-hydroxythreonine
-
low-specificity L-threonine aldolase is involved in a serendipitous pathway that converts 3-phosphohydroxypyruvate, an intermediate in the serine biosynthesis pathway, to L-4-phosphohydroxythreonine, an intermediate in the pyridoxal-5'-phosphate synthesis pathway in a strain of Escherichia coli that lacks 4-phosphoerythronate dehydrogenase
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-
r
L-4-hydroxythreonine
glycine + glycolaldehyde
-
cleavage of L-4-hydroxythreonine is as efficient as cleavage of L-allo-threonine
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-
r
N-(S)-benzyloxycarbonyl-alaninal + glycine
(2S,3R,4S)-2-amino-4-(benzyloxycarbonylamino)-3-hydroxypentanoic acid
N-(S)-benzyloxycarbonyl-alaninal + glycine
(2S,3S,4S)-2-amino-4-(benzyloxycarbonylamino)-3-hydroxypentanoic acid
-
conversion: 54%, glycine concentration: 140 mM, reaction temperature: 25°C, yield: 27%, L-erythro/L-threo: 18:82
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-
?
N-benzyloxycarbonyl-3-aminopropanal + glycine
(2S,3R)-2-amino-5-(benzyloxycarbonylamino)-3-hydroxypentanoic acid
N-benzyloxycarbonyl-3-aminopropanal + glycine
(2S,3S)-2-amino-5-(benzyloxycarbonylamino)-3-hydroxypentanoic acid
N-benzyloxycarbonyl-glycinal + glycine
(2S,3R)-2-amino-4-(benzyloxycarbonylamino)-3-hydroxybutanoic acid
N-benzyloxycarbonyl-glycinal + glycine
(2S,3S)-2-amino-4-(benzyloxycarbonylamino)-3-hydroxybutanoic acid
(R)-N-Cbz-alaninal + glycine
(2S,3R,4R)-2-amino-4-(benzyloxycarbonylamino)-3-hydroxypentanoic acid
-
conversion: 40%, glycine concentration: 70 mM, reaction temperature: 4°C, yield: 30%, L-erythro/L-threo: 16:84
-
-
?
(R)-N-Cbz-alaninal + glycine
(2S,3R,4R)-2-amino-4-(benzyloxycarbonylamino)-3-hydroxypentanoic acid
-
conversion: 60%, glycine concentration: 70 mM, reaction temperature: 4°C, yield: 30%, L-erythro/L-threo: 100:0
-
-
?
benzyloxyacetaldehyde + glycine
(2S,3R)-2-amino-4-(benzyloxy)-3-hydroxybutanoic acid
-
conversion: 45%, glycine concentration: 140 mM, reaction temperature: 25°C, yield: 30%, L-erythro/L-threo: 40:60
-
-
?
benzyloxyacetaldehyde + glycine
(2S,3R)-2-amino-4-(benzyloxy)-3-hydroxybutanoic acid
-
conversion: 68%, glycine concentration: 70 mM, reaction temperature: 4°C, yield: 40%, L-erythro/L-threo: 97:3
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-
?
DL-threo-phenylserine
glycine + benzaldehyde
180% of the activity with L-threonine
-
-
?
glycine + 3,4-dihydroxybenzaldehyde
L-threo-3,4-dihydroxyphenylserine
-
-
-
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r
glycine + 3,4-dihydroxybenzaldehyde
L-threo-3,4-dihydroxyphenylserine
-
L-threo-3,4-dihydroxyphenylserine synthesis activity is dramatically decreased when the condensation reaction is repeated
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-
?
glycine + 3,4-dihydroxybenzaldehyde
L-threo-3,4-dihydroxyphenylserine
-
L-threo-3,4-dihydroxyphenylserine synthesis activity is dramatically decreased when the condensation reaction is repeated
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-
?
glycine + 3,4-dihydroxybenzaldehyde
L-threo-3,4-dihydroxyphenylserine + L-erythro-3,4-dihydroxyphenylserine
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-
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r
glycine + 3,4-dihydroxybenzaldehyde
L-threo-3,4-dihydroxyphenylserine + L-erythro-3,4-dihydroxyphenylserine
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-
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r
L-allo-threonine
glycine + acetaldehyde
291% of the activity with L-threonine
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-
?
L-threo-3,4-dihydroxyphenylserine
glycine + 3,4-dihydroxybenzaldehyde
-
-
-
-
?
L-threo-3,4-dihydroxyphenylserine
glycine + 3,4-dihydroxybenzaldehyde
-
-
-
-
?
L-threo-beta-3,4-dihydroxyphenylserine
glycine + 3,4-dihydroxybenzaldehyde
-
-
-
?
L-threo-beta-3,4-dihydroxyphenylserine
glycine + 3,4-dihydroxybenzaldehyde
-
-
-
?
N-(S)-benzyloxycarbonyl-alaninal + glycine
(2S,3R,4S)-2-amino-4-(benzyloxycarbonylamino)-3-hydroxypentanoic acid
-
conversion: 54%, glycine concentration: 140 mM, reaction temperature: 25°C, yield: 27%, L-erythro/L-threo: 18:82
-
-
?
N-(S)-benzyloxycarbonyl-alaninal + glycine
(2S,3R,4S)-2-amino-4-(benzyloxycarbonylamino)-3-hydroxypentanoic acid
-
conversion: 48%, glycine concentration: 280 mM, reaction temperature: 4°C, yield: 30%, L-erythro/L-threo: 100:0
-
-
?
N-benzyloxycarbonyl-3-aminopropanal + glycine
(2S,3R)-2-amino-5-(benzyloxycarbonylamino)-3-hydroxypentanoic acid
-
conversion: 49%, glycine concentration: 70 mM, reaction temperature: 25°C, yield: 11%, L-erythro/L-threo: 50:50
-
-
?
N-benzyloxycarbonyl-3-aminopropanal + glycine
(2S,3R)-2-amino-5-(benzyloxycarbonylamino)-3-hydroxypentanoic acid
-
conversion: 34%, glycine concentration: 70 mM, reaction temperature: 25°C, yield: 10%, L-erythro/L-threo: 50:50
-
-
?
N-benzyloxycarbonyl-3-aminopropanal + glycine
(2S,3S)-2-amino-5-(benzyloxycarbonylamino)-3-hydroxypentanoic acid
-
conversion: 49%, glycine concentration: 70 mM, reaction temperature: 25°C, yield: 11%, L-erythro/L-threo: 50:50
-
-
?
N-benzyloxycarbonyl-3-aminopropanal + glycine
(2S,3S)-2-amino-5-(benzyloxycarbonylamino)-3-hydroxypentanoic acid
-
conversion: 20%, glycine concentration: 70 mM, reaction temperature: 4°C, yield: 3%, L-erythro/L-threo: 100:0
-
-
?
N-benzyloxycarbonyl-glycinal + glycine
(2S,3R)-2-amino-4-(benzyloxycarbonylamino)-3-hydroxybutanoic acid
-
conversion: 60%, glycine concentration: 140 mM, reaction temperature: 25°C, yield: 18%, L-erythro/L-threo: 30:70
-
-
?
N-benzyloxycarbonyl-glycinal + glycine
(2S,3R)-2-amino-4-(benzyloxycarbonylamino)-3-hydroxybutanoic acid
-
conversion: 35%, glycine concentration: 70 mM, reaction temperature: 4°C, yield: 13%, L-erythro/L-threo: 86:14
-
-
?
N-benzyloxycarbonyl-glycinal + glycine
(2S,3S)-2-amino-4-(benzyloxycarbonylamino)-3-hydroxybutanoic acid
-
conversion: 60%, glycine concentration: 140 mM, reaction temperature: 25°C, yield: 18%, L-erythro/L-threo: 30:70
-
-
?
N-benzyloxycarbonyl-glycinal + glycine
(2S,3S)-2-amino-4-(benzyloxycarbonylamino)-3-hydroxybutanoic acid
-
conversion: 35%, glycine concentration: 70 mM, reaction temperature: 4°C, yield: 13%, L-erythro/L-threo: 86:14
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-
?
additional information
?
-
-
by manipulating reaction parameters, SHMT yields exclusively L-erythro diastereomers in 34-60% conversion. SHMT is among the most stereoselective L-threonine aldolases described. This is due to its activity-temperature dependence: at 4°C SHMT has high synthetic activity but negligible retro-aldol activity on l-threonine. Thus, the kinetic l-erythro isomer is largely favored and the reactions are virtually irreversible, highly stereoselective, and in turn, give excellent conversion
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-
?
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NATURAL SUBSTRATE
NATURAL 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
glycine + glycolaldehyde
L-4-hydroxythreonine
-
low-specificity L-threonine aldolase is involved in a serendipitous pathway that converts 3-phosphohydroxypyruvate, an intermediate in the serine biosynthesis pathway, to L-4-phosphohydroxythreonine, an intermediate in the pyridoxal-5'-phosphate synthesis pathway in a strain of Escherichia coli that lacks 4-phosphoerythronate dehydrogenase
-
-
r
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COFACTOR
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
pyridoxal 5'-phosphate
-
contains 6 mol of pyridoxal 5'-phosphate per mol of enzyme
pyridoxal 5'-phosphate
2 mol pyridoxal 5'-phosphate per 4 mol of subunit
pyridoxal 5'-phosphate
contains 1 mol of pyridoxal 5'-phosphate as cofactor per mol of 36500 Da subunit
pyridoxal 5'-phosphate
contains 1 mol of pyridoxal 5'-phosphate per mol of 38000 da subunit. Lys207 probably functions as an essential catalytic residue, forming an internal Schiff base with the pyridoxal 5'-phosphate of the enzyme to catalyze the reversible aldol reaction
pyridoxal 5'-phosphate
-
Km: 0.00025 mM, 1 mol of pyridoxal phosphate binds 46000 g of protein
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METALS and IONS
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
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INHIBITOR
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
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ACTIVATING COMPOUND
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
sodium sulfite
addition of sodium sulfite stimulates the production of L-threo-3,4-dihydroxyphenylserine without affecting the diastereoselectivity ratio, especially at 50 mM
Triton X-100
highest conversion yield at a 0.75% without affecting the diastereoselectivity ratio
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DISEASE
TITLE OF PUBLICATION
LINK TO PUBMED
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KM VALUE [mM]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
0.000002
L-phenylserine
-
recombinant wild type enzyme, in 50 mM Tris-HCl buffer (pH 8.0)
0.0000026
L-phenylserine
-
mutant enzyme H177Y, in 50 mM Tris-HCl buffer (pH 8.0)
0.00016
L-Thr
-
mutant enzyme H177Y, in 50 mM Tris-HCl buffer (pH 8.0)
0.00018
L-Thr
-
recombinant wild type enzyme, in 50 mM Tris-HCl buffer (pH 8.0)
0.0002
L-threo-3,4-dihydroxyphenylserine
-
recombinant wild type enzyme, in 50 mM Tris-HCl buffer (pH 8.0)
0.00023
L-threo-3,4-dihydroxyphenylserine
-
mutant enzyme H177Y, in 50 mM Tris-HCl buffer (pH 8.0)
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TURNOVER NUMBER [1/s]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
0.000107
L-phenylserine
-
recombinant wild type enzyme, in 50 mM Tris-HCl buffer (pH 8.0)
0.000113
L-phenylserine
-
mutant enzyme H177Y, in 50 mM Tris-HCl buffer (pH 8.0)
0.0178
L-Thr
-
mutant enzyme H177Y, in 50 mM Tris-HCl buffer (pH 8.0)
0.0195
L-Thr
-
recombinant wild type enzyme, in 50 mM Tris-HCl buffer (pH 8.0)
0.00022
L-threo-3,4-dihydroxyphenylserine
-
recombinant wild type enzyme, in 50 mM Tris-HCl buffer (pH 8.0)
0.00023
L-threo-3,4-dihydroxyphenylserine
-
mutant enzyme H177Y, in 50 mM Tris-HCl buffer (pH 8.0)
0.33