4.1.2.48: low-specificity L-threonine aldolase
This is an abbreviated version!
For detailed information about low-specificity L-threonine aldolase, go to the full flat file.
Word Map on EC 4.1.2.48
Reaction
Synonyms
GLY1, GlyA, L-TA, L-threonine aldolase, low specificity L-TA, low specificity threonine aldolase, Low-specificity L-threonine aldolase, LTA, LtaE, serine hydroxy-methyl transferase, SHMT, threonine aldolase
ECTree
4.1.2.48 low-specificity L-threonine aldolaseAdvanced search results
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results (Substrates Products
Substrates Products on EC 4.1.2.48 - low-specificity L-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
-
-
?
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
-
-
r
L-4-hydroxythreonine
glycine + glycolaldehyde
-
cleavage of L-4-hydroxythreonine is as efficient as cleavage of L-allo-threonine
-
-
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
-
-
?
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
-
-
?
DL-threo-phenylserine
glycine + benzaldehyde
180% of the activity with L-threonine
-
-
?
glycine + 3,4-dihydroxybenzaldehyde
L-threo-3,4-dihydroxyphenylserine
-
-
-
-
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
-
-
?
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
-
-
?
glycine + 3,4-dihydroxybenzaldehyde
L-threo-3,4-dihydroxyphenylserine + L-erythro-3,4-dihydroxyphenylserine
-
-
-
-
r
glycine + 3,4-dihydroxybenzaldehyde
L-threo-3,4-dihydroxyphenylserine + L-erythro-3,4-dihydroxyphenylserine
-
-
-
-
r
L-allo-threonine
glycine + acetaldehyde
291% of the activity with L-threonine
-
-
?
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
-
-
?
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
-
-
?
