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Literature summary extracted from

  • ST.Maurice, M.; Bearne, S.L.
    Reaction intermediate analogues for mandelate racemase: interaction between Asn 197 and the alpha-hydroxyl of the substrate promotes catalysis (2000), Biochemistry, 39, 13324-13335.
    View publication on PubMed

Protein Variants

EC Number Protein Variants Comment Organism
5.1.2.2 N197A turnover number is reduced 30fold for (R)-mandelate and 179fold for (S)-mandelate relative to wild-type enzyme. The ratio of turnover number to Km-value is reduced 208fold for (R)-mandelate and 556fold for (S)-mandelate, 3.5fold reduction in affinity for the substrate analogue (R)-atrolactate, but 51fold and 18fold reduction in affinity for alpha-hydroxybenzylphosphonate and benzohydroxamate, respectively Pseudomonas putida

Inhibitors

EC Number Inhibitors Comment Organism Structure
5.1.2.2 (R)-atrolactate
-
 Pseudomonas putida
5.1.2.2 (R,S)-alpha-hydroxybenzylphosphonate
-
 Pseudomonas putida
5.1.2.2 (R,S)-methyl-alpha-hydroxybenzylphosphonate
-
 Pseudomonas putida
5.1.2.2 benzohydroxamate
-
 Pseudomonas putida
5.1.2.2 benzoylformate
-
 Pseudomonas putida
5.1.2.2 benzoylhydroxamate
-
 Pseudomonas putida
5.1.2.2 benzoylphosphonate
-
 Pseudomonas putida
5.1.2.2 benzylphosphonate
-
 Pseudomonas putida
5.1.2.2 phenylacetate
-
 Pseudomonas putida

KM Value [mM]

EC Number KM Value [mM] KM Value Maximum [mM] Substrate Comment Organism Structure
5.1.2.2 0.62
-
 (S)-Mandelate
-
 Pseudomonas putida
5.1.2.2 0.62
-
 (S)-Mandelate 25°C, pH 7.5, wild-type enzyme Pseudomonas putida
5.1.2.2 0.81
-
 (R)-mandelate
-
 Pseudomonas putida
5.1.2.2 0.81
-
 (R)-mandelate 25°C, pH 7.5, wild-type enzyme Pseudomonas putida
5.1.2.2 1.4
-
 (S)-Mandelate 25°C, pH 7.5, mutant enzyme N197A Pseudomonas putida
5.1.2.2 5.4
-
 (R)-mandelate 25°C, pH 7.5, mutant enzyme N197A Pseudomonas putida

Metals/Ions

EC Number Metals/Ions Comment Organism Structure
5.1.2.2 Mg2+ Km: 0.65 mM for wild-type enzyme and 0.34 mM for mutant enzyme N197A Pseudomonas putida

Natural Substrates/ Products (Substrates)

EC Number Natural Substrates Organism Comment (Nat. Sub.) Natural Products Comment (Nat. Pro.) Rev. Reac.
5.1.2.2 D-mandelate Pseudomonas putida
-
 L-mandelate
-
 r

Organism

EC Number Organism UniProt Comment Textmining
5.1.2.2 Pseudomonas putida
-
-
-

Reaction

EC Number Reaction Comment Organism Reaction ID
5.1.2.2 (S)-mandelate = (R)-mandelate free energy profile for racemization Pseudomonas putida
a

Substrates and Products (Substrate)

EC Number Substrates Comment Substrates Organism Products Comment (Products) Rev. Reac.
5.1.2.2 (R)-mandelate
-
 Pseudomonas putida (S)-mandelate
-
 ?
5.1.2.2 D-mandelate
-
 Pseudomonas putida L-mandelate
-
 r

Synonyms

EC Number Synonyms Comment Organism
5.1.2.2 MR
-
 Pseudomonas putida

Turnover Number [1/s]

EC Number Turnover Number Minimum [1/s] Turnover Number Maximum [1/s] Substrate Comment Organism Structure
5.1.2.2 2.5
-
 (S)-Mandelate 25°C, pH 7.5, mutant enzyme N197A Pseudomonas putida
5.1.2.2 16.9
-
 (R)-mandelate 25°C, pH 7.5, mutant enzyme N197A Pseudomonas putida
5.1.2.2 447
-
 (S)-Mandelate
-
 Pseudomonas putida
5.1.2.2 447
-
 (S)-Mandelate 25°C, pH 7.5, wild-type enzyme Pseudomonas putida
5.1.2.2 514
-
 (R)-mandelate
-
 Pseudomonas putida
5.1.2.2 514
-
 (R)-mandelate 25°C, pH 7.5, wild-type enzyme Pseudomonas putida

Ki Value [mM]

EC Number Ki Value [mM] Ki Value maximum [mM] Inhibitor Comment Organism Structure
5.1.2.2 0.0047
-
 (R,S)-alpha-hydroxybenzylphosphonate 25°C, pH 7.5, wild-type enzyme Pseudomonas putida
5.1.2.2 0.0087
-
 (R,S)-alpha-hydroxybenzylphosphonate
-
 Pseudomonas putida
5.1.2.2 0.0093
-
 benzohydroxamic acid
-
 Pseudomonas putida
5.1.2.2 0.0117
-
 benzohydroxamate 25°C, pH 7.5, wild-type enzyme Pseudomonas putida
5.1.2.2 0.2
-
 phenylacetate
-
 Pseudomonas putida
5.1.2.2 0.216
-
 benzohydroxamate 25°C, pH 7.5, mutant enzyme N197A Pseudomonas putida
5.1.2.2 0.238
-
 (R,S)-alpha-hydroxybenzylphosphonate 25°C, pH 7.5, mutant enzyme N197A Pseudomonas putida
5.1.2.2 0.3
-
 benzoylphosphonate
-
 Pseudomonas putida
5.1.2.2 0.65
-
 benzoylformate
-
 Pseudomonas putida
5.1.2.2 0.95
-
 (R)-atrolactate wild-type enzyme Pseudomonas putida
5.1.2.2 0.95
-
 (R)-atrolactate 25°C, pH 7.5, wild-type enzyme Pseudomonas putida
5.1.2.2 3.3
-
 (R)-atrolactate mutant N197A Pseudomonas putida
5.1.2.2 3.3
-
 (R)-atrolactate 25°C, pH 7.5, mutant enzyme N197A Pseudomonas putida
5.1.2.2 3.5
-
 benzylphosphonate
-
 Pseudomonas putida
5.1.2.2 5.1
-
 (R,S)-methyl-alpha-hydroxybenzylphosphonate
-
 Pseudomonas putida