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Literature summary extracted from

  • Fesko, K.; Giger, L.; Hilvert, D.
    Synthesis of beta-hydroxy-alpha-amino acids with a reengineered alanine racemase (2008), Bioorg. Med. Chem. Lett., 18, 5987-5990.
    View publication on PubMed

Application

EC Number Application Comment Organism
4.1.2.42 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 Geobacillus stearothermophilus

Protein Variants

EC Number Protein Variants Comment Organism
4.1.2.42 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 Geobacillus stearothermophilus

Metals/Ions

EC Number Metals/Ions Comment Organism Structure
4.1.2.42 additional information Mg2+ ions show no effect on both selectivity and activity Geobacillus stearothermophilus

Organism

EC Number Organism UniProt Comment Textmining
4.1.2.42 Geobacillus stearothermophilus
-
-
-

Substrates and Products (Substrate)

EC Number Substrates Comment Substrates Organism Products Comment (Products) Rev. Reac.
4.1.2.42 D-alanine + 3-nitrobenzaldehyde 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 Geobacillus stearothermophilus (betaS)-beta-hydroxy-alpha-methyl-3-nitro-D-phenylalanine
-
 r
4.1.2.42 glycine + 2-aminobenzaldehyde 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 Geobacillus stearothermophilus (betaS)-2-amino-beta-hydroxy-D-phenylalanine
-
 r
4.1.2.42 glycine + 2-nitrobenzaldehyde 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 Geobacillus stearothermophilus (betaS)-beta-hydroxy-2-nitro-D-phenylalanine
-
 r
4.1.2.42 glycine + 3-hydroxybenzaldehyde 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 Geobacillus stearothermophilus (betaS)-beta,3-dihydroxy-D-phenylalanine
-
 r
4.1.2.42 glycine + 3-nitrobenzaldehyde 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 Geobacillus stearothermophilus (betaS)-beta-hydroxy-3-nitro-D-phenylalanine
-
 r
4.1.2.42 glycine + 4-nitrobenzaldehyde 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 Geobacillus stearothermophilus (betaS)-beta-hydroxy-4-nitro-D-phenylalanine
-
 r
4.1.2.42 glycine + benzaldehyde 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 Geobacillus stearothermophilus (betaS)-beta-hydroxy-D-phenylalanine
-
 r
4.1.2.42 glycine + piperonal 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 Geobacillus stearothermophilus (3S)-3-(1,3-benzodioxol-5-yl)-D-serine
-
 r
4.1.2.42 additional information no aldol condensation of glycine with n-pentanal or 2-methylpropanal Geobacillus stearothermophilus ?
-
 ?

Temperature Optimum [°C]

EC Number Temperature Optimum [°C] Temperature Optimum Maximum [°C] Comment Organism
4.1.2.42 50
-
 temperature-optimum for yield, but less diastereoselectivity, origin thermophilic organism Geobacillus stearothermophilus

Temperature Range [°C]

EC Number Temperature Minimum [°C] Temperature Maximum [°C] Comment Organism
4.1.2.42 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 Geobacillus stearothermophilus

pH Optimum

EC Number pH Optimum Minimum pH Optimum Maximum Comment Organism
4.1.2.42 9.5
-
 pH-optimum for yield, but less diastereoselectivity Geobacillus stearothermophilus

Cofactor

EC Number Cofactor Comment Organism Structure
4.1.2.42 pyridoxal 5'-phosphate
-
 Geobacillus stearothermophilus