Ligand (S)-2-hydroxyglutarate

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Basic Ligand Information

Molecular Structure
Picture of (S)-2-hydroxyglutarate (click for magnification)
Molecular Formula
BRENDA Name
InChIKey
C5H8O5
(S)-2-hydroxyglutarate
HWXBTNAVRSUOJR-VKHMYHEASA-N
Synonyms:
L-(-)alpha-hydroxyglutarate, L-2-hydroxyglutarate, L-2-hydroxyglutaric acid, L-alpha-hydroxyglutarate, L-alpha-hydroxyglutaric acid

Roles as Enzyme Ligand

In Vivo Substrate in Enzyme-catalyzed Reactions (9 results)

EC NUMBER
PROVEN IN VIVO REACTION
REACTION DIAGRAM
LITERATURE
ENZYME 3D STRUCTURE

Substrate in Enzyme-catalyzed Reactions (23 results)

EC NUMBER
REACTION
REACTION DIAGRAM
LITERATURE
ENZYME 3D STRUCTURE
(S)-2-hydroxyglutarate + NAD+ = 2-oxoglutarate + NADH + H+
show the reaction diagram
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(S)-2-hydroxyglutarate + NAD+ = 2-oxoglutarate + NADH + H+
show the reaction diagram
-
glutaconyl-CoA + (S)-2-hydroxyglutarate = glutaconate + (S)-2-hydroxyglutaryl-CoA
show the reaction diagram
-

Product in Enzyme-catalyzed Reactions (7 results)

EC NUMBER
REACTION
REACTION DIAGRAM
LITERATURE
ENZYME 3D STRUCTURE
2-oxoglutarate + NADH + H+ = L-2-hydroxyglutarate + NAD+
show the reaction diagram
-
-
2-oxoglutarate + NADH + H+ = (S)-2-hydroxyglutarate + NAD+
show the reaction diagram
-
-
glutarate + 2-oxoglutarate + O2 = (S)-2-hydroxyglutarate + succinate + CO2
show the reaction diagram
-
-
(S)-5-oxo-2-tetrahydrofurancarboxylic acid + H2O = L-alpha-hydroxyglutaric acid
show the reaction diagram
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(S)-5-oxo-2-tetrahydrofurancarboxylic acid + H2O = L-alpha-hydroxyglutaric acid
show the reaction diagram
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-
L-2-hydroxyglutaramate + H2O = L-2-hydroxyglutarate + NH3
show the reaction diagram
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-
(S)-5-oxo-2-tetrahydrofurancarboxylic acid = L-alpha-hydroxyglutaric acid
show the reaction diagram
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-

Inhibitor in Enzyme-catalyzed Reactions (5 results)

EC NUMBER
COMMENTARY
LITERATURE
ENZYME 3D STRUCTURE
the enzyme activity is inhibited by L-alpha-hydroxyglutarate but not its enantiomer D-alpha-hydroxyglutarate
-
weak product inhibition
-

3D Structure of Enzyme-Ligand-Complex (PDB) (2 results)

EC NUMBER
ENZYME 3D STRUCTURE

Enzyme Kinetic Parameters

kcat Value (Turnover Number) (5 results)

EC NUMBER
TURNOVER NUMBER [1/S]
TURNOVER NUMBER MAXIMUM [1/S]
COMMENTARY
LITERATURE
613
-
at pH 7.4 and 30°C
0.05
-
pH 7.0

KM Value (13 results)

EC NUMBER
KM VALUE [MM]
KM VALUE MAXIMUM [MM]
COMMENTARY
LITERATURE
14
-
cosubstrate glutaconyl-CoA
1.2
-
pH 7.0

Ki Value (1 result)

EC NUMBER
KI VALUE [MM]
KI VALUE MAXIMUM [MM]
COMMENTARY
LITERATURE
0.25
-
-

IC50 Value (2 results)

EC NUMBER
IC50 VALUE
IC50 VALUE MAXIMUM
COMMENTARY
LITERATURE
2
-
in 50 mM Tris-HCl (pH 8.0) with 50 mM NaCl, 1 mM dithiothreitol, at 22°C
0.097
-
pH and temperature not specified in the publication

References & Links

Links to other databases for (S)-2-hydroxyglutarate

ChEBI
PubChem
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PubChem