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Literature summary for 4.1.2.42 extracted from

  • Steinreiber, J.; Fesko, K.; Reisinger, C.; Schuermann, M.; van Assema, F.; Wolberg, M.; Mink, D.; Griengl, H.
    Threonine aldolases-an emerging tool for organic synthesis (2006), Tetrahedron, 63, 918-926.
No PubMed abstract available
Search for more literature for 4.1.2.42

Cloned(Commentary)

Cloned (Comment) Organism
cloned in Escherichia coli Achromobacter xylosoxidans

Metals/Ions

Metals/Ions Comment Organism Structure
MnCl2
-
 Achromobacter xylosoxidans

Organism

Organism UniProt Comment Textmining
Achromobacter xylosoxidans
-
-
-

Substrates and Products (Substrate)

Substrates Comment Substrates Organism Products Comment (Products) Rev. Reac.
2-bromobenzaldehyde + glycine 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 Achromobacter xylosoxidans D-2-bromophenylserine
-
 ?
2-chlorobenzaldehyde + glycine 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 Achromobacter xylosoxidans D-2-chlorophenylserine
-
 ?
2-fluorobenzaldehyde + glycine 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 Achromobacter xylosoxidans D-2-fluorophenylserine
-
 ?
2-nitrobenzaldehyde + glycine 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 Achromobacter xylosoxidans D-2-nitrophenylserine
-
 ?
3,4-methylenedioxybenzaldehyde + glycine 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 Achromobacter xylosoxidans D-3,4-methylenedioxyphenylserine
-
 ?
3-bromobenzaldehyde + glycine 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 Achromobacter xylosoxidans D-3-bromophenylserine
-
 ?
3-chlorobenzaldehyde + glycine 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 Achromobacter xylosoxidans D-3-chlorophenylserine
-
 ?
3-fluorobenzaldehyde + glycine 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 Achromobacter xylosoxidans D-3-fluorophenylserine
-
 ?
3-hydroxybenzaldehyde + glycine 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 Achromobacter xylosoxidans D-3-hydroxyphenylserine
-
 ?
3-nitrobenzaldehyde + glycine 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 Achromobacter xylosoxidans D-3-nitrophenylserine
-
 ?
4-(methylsulfonyl)benzaldehyde + glycine 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 Achromobacter xylosoxidans D-3-(4-methylsulfonylphenyl)serine
-
 ?
4-bromobenzaldehyde + glycine 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 Achromobacter xylosoxidans D-4-bromophenylserine
-
 ?
4-chlorobenzaldehyde + glycine 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 Achromobacter xylosoxidans D-4-chlorophenylserine
-
 ?
4-fluorobenzaldehyde + glycine 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 Achromobacter xylosoxidans D-4-fluorophenylserine
-
 ?
4-formylbenzenesulfonamide + glycine 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 Achromobacter xylosoxidans D-2-amino-3-hydroxy-3-(4-sulfamoylphenyl)-propanoic acid
-
 ?
4-hydroxybenzaldehyde + glycine 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 Achromobacter xylosoxidans D-4-hydroxyphenylserine
-
 ?
4-nitrobenzaldehyde + glycine 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 Achromobacter xylosoxidans D-4-nitrophenylserine
-
 ?
benzaldehyde + glycine 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 Achromobacter xylosoxidans D-phenylserine
-
 ?
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 Achromobacter xylosoxidans ?
-
 ?
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 Achromobacter xylosoxidans ?
-
 ?

Synonyms

Synonyms Comment Organism
D-threonine aldolase
-
 Achromobacter xylosoxidans
DTA
-
 Achromobacter xylosoxidans

Temperature Optimum [°C]

Temperature Optimum [°C] Temperature Optimum Maximum [°C] Comment Organism
5
-
-
 Achromobacter xylosoxidans

Temperature Range [°C]

Temperature Minimum [°C] Temperature Maximum [°C] Comment Organism
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 Achromobacter xylosoxidans

pH Optimum

pH Optimum Minimum pH Optimum Maximum Comment Organism
8
-
 assay at Achromobacter xylosoxidans

pH Range

pH Minimum pH Maximum Comment Organism
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 Achromobacter xylosoxidans

Cofactor

Cofactor Comment Organism Structure
pyridoxal 5'-phosphate
-
 Achromobacter xylosoxidans