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Literature summary for 4.1.2.48 extracted from

  • Gutierrez, M.L.; Garrabou, X.; Agosta, E.; Servi, S.; Parella, T.; Joglar, J.; Clapes, P.
    Serine hydroxymethyl transferase from Streptococcus thermophilus and L-threonine aldolase from Escherichia coli as stereocomplementary biocatalysts for the synthesis of beta-hydroxy-alpha,omega-diamino acid derivatives (2008), Chemistry, 14, 4647-4656.
    View publication on PubMed
Search for more literature for 4.1.2.48

Organism

Organism UniProt Comment Textmining
Escherichia coli
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-
-
Streptococcus thermophilus
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-
-

Substrates and Products (Substrate)

Substrates Comment Substrates Organism Products Comment (Products) Rev. Reac.
(R)-N-Cbz-alaninal + glycine conversion: 40%, glycine concentration: 70 mM, reaction temperature: 4°C, yield: 30%, L-erythro/L-threo: 16:84 Escherichia coli (2S,3R,4R)-2-amino-4-(benzyloxycarbonylamino)-3-hydroxypentanoic acid
-
 ?
(R)-N-Cbz-alaninal + glycine conversion: 60%, glycine concentration: 70 mM, reaction temperature: 4°C, yield: 30%, L-erythro/L-threo: 100:0 Streptococcus thermophilus (2S,3R,4R)-2-amino-4-(benzyloxycarbonylamino)-3-hydroxypentanoic acid
-
 ?
(R)-N-Cbz-alaninal + glycine conversion: 40%, glycine concentration: 70 mM, reaction temperature: 4°C, yield: 30%, L-erythro/L-threo: 16:84 Escherichia coli (2S,3S,4R)-2-amino-4-(benzyloxycarbonylamino)-3-hydroxypentanoic acid
-
 ?
benzyloxyacetaldehyde + glycine conversion: 45%, glycine concentration: 140 mM, reaction temperature: 25°C, yield: 30%, L-erythro/L-threo: 40:60 Escherichia coli (2S,3R)-2-amino-4-(benzyloxy)-3-hydroxybutanoic acid
-
 ?
benzyloxyacetaldehyde + glycine conversion: 68%, glycine concentration: 70 mM, reaction temperature: 4°C, yield: 40%, L-erythro/L-threo: 97:3 Streptococcus thermophilus (2S,3R)-2-amino-4-(benzyloxy)-3-hydroxybutanoic acid
-
 ?
benzyloxyacetaldehyde + glycine conversion: 45%, glycine concentration: 140 mM, reaction temperature: 25°C, yield: 30%, L-erythro/L-threo: 40:60 Escherichia coli (2S,3S)-2-amino-4-(benzyloxy)-3-hydroxybutanoic acid
-
 ?
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 Streptococcus thermophilus ?
-
 ?
N-(S)-benzyloxycarbonyl-alaninal + glycine conversion: 48%, glycine concentration: 280 mM, reaction temperature: 4°C, yield: 30%, L-erythro/L-threo: 100:0 Streptococcus thermophilus (2S,3R,4S)-2-amino-4-(benzyloxycarbonylamino)-3-hydroxypentanoic acid
-
 ?
N-(S)-benzyloxycarbonyl-alaninal + glycine conversion: 54%, glycine concentration: 140 mM, reaction temperature: 25°C, yield: 27%, L-erythro/L-threo: 18:82 Escherichia coli (2S,3R,4S)-2-amino-4-(benzyloxycarbonylamino)-3-hydroxypentanoic acid
-
 ?
N-(S)-benzyloxycarbonyl-alaninal + glycine conversion: 54%, glycine concentration: 140 mM, reaction temperature: 25°C, yield: 27%, L-erythro/L-threo: 18:82 Escherichia coli (2S,3S,4S)-2-amino-4-(benzyloxycarbonylamino)-3-hydroxypentanoic acid
-
 ?
N-benzyloxycarbonyl-3-aminopropanal + glycine conversion: 34%, glycine concentration: 70 mM, reaction temperature: 25°C, yield: 10%, L-erythro/L-threo: 50:50 Streptococcus thermophilus (2S,3R)-2-amino-5-(benzyloxycarbonylamino)-3-hydroxypentanoic acid
-
 ?
N-benzyloxycarbonyl-3-aminopropanal + glycine conversion: 49%, glycine concentration: 70 mM, reaction temperature: 25°C, yield: 11%, L-erythro/L-threo: 50:50 Escherichia coli (2S,3R)-2-amino-5-(benzyloxycarbonylamino)-3-hydroxypentanoic acid
-
 ?
N-benzyloxycarbonyl-3-aminopropanal + glycine conversion: 20%, glycine concentration: 70 mM, reaction temperature: 4°C, yield: 3%, L-erythro/L-threo: 100:0 Streptococcus thermophilus (2S,3S)-2-amino-5-(benzyloxycarbonylamino)-3-hydroxypentanoic acid
-
 ?
N-benzyloxycarbonyl-3-aminopropanal + glycine conversion: 49%, glycine concentration: 70 mM, reaction temperature: 25°C, yield: 11%, L-erythro/L-threo: 50:50 Escherichia coli (2S,3S)-2-amino-5-(benzyloxycarbonylamino)-3-hydroxypentanoic acid
-
 ?
N-benzyloxycarbonyl-glycinal + glycine conversion: 35%, glycine concentration: 70 mM, reaction temperature: 4°C, yield: 13%, L-erythro/L-threo: 86:14 Streptococcus thermophilus (2S,3R)-2-amino-4-(benzyloxycarbonylamino)-3-hydroxybutanoic acid
-
 ?
N-benzyloxycarbonyl-glycinal + glycine conversion: 60%, glycine concentration: 140 mM, reaction temperature: 25°C, yield: 18%, L-erythro/L-threo: 30:70 Escherichia coli (2S,3R)-2-amino-4-(benzyloxycarbonylamino)-3-hydroxybutanoic acid
-
 ?
N-benzyloxycarbonyl-glycinal + glycine conversion: 35%, glycine concentration: 70 mM, reaction temperature: 4°C, yield: 13%, L-erythro/L-threo: 86:14 Streptococcus thermophilus (2S,3S)-2-amino-4-(benzyloxycarbonylamino)-3-hydroxybutanoic acid
-
 ?
N-benzyloxycarbonyl-glycinal + glycine conversion: 60%, glycine concentration: 140 mM, reaction temperature: 25°C, yield: 18%, L-erythro/L-threo: 30:70 Escherichia coli (2S,3S)-2-amino-4-(benzyloxycarbonylamino)-3-hydroxybutanoic acid
-
 ?

Synonyms

Synonyms Comment Organism
L-threonine aldolase
-
 Escherichia coli
LTA
-
 Escherichia coli
serine hydroxy-methyl transferase
-
 Streptococcus thermophilus
SHMT
-
 Streptococcus thermophilus

pH Optimum

pH Optimum Minimum pH Optimum Maximum Comment Organism
6.5
-
 assay at Streptococcus thermophilus
8
-
 assay at Escherichia coli

Cofactor

Cofactor Comment Organism Structure
pyridoxal 5'-phosphate
-
 Escherichia coli
pyridoxal 5'-phosphate
-
 Streptococcus thermophilus