Literature summary for 5.1.2.2 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.

Search for more literature for 5.1.2.2

Protein Variants

Protein Variants	Comment	Organism
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

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

KM Value [mM]

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

Metals/Ions

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

Natural Substrates/ Products (Substrates)

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

Organism

Organism	UniProt	Comment	Textmining
Pseudomonas putida	-	-	-

Reaction

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

Substrates and Products (Substrate)

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

Synonyms

Synonyms	Comment	Organism
MR	-	Pseudomonas putida

Turnover Number [1/s]

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

Ki Value [mM]

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

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Release 2023.1 (January 2023)