Ligand (S)-mandelic acid

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Basic Ligand Information

Molecular Structure
Picture of (S)-mandelic acid (click for magnification)
Molecular Formula
BRENDA Name
InChIKey
C8H8O3
(S)-mandelic acid
IWYDHOAUDWTVEP-ZETCQYMHSA-N
Synonyms:
(2S)-hydroxy(phenyl)acetic acid, (2S)-hydroxy(phenyl)ethanoic acid, (S)-(+)-mandelate, (S)-2-Hydroxy-2-phenylacetate, (S)-alpha-hydroxyphenylacetic acid, (S)-Mandelate, L-Mandelate, S-mandelate

Roles as Enzyme Ligand

In Vivo Substrate in Enzyme-catalyzed Reactions (7 results)

EC NUMBER
PROVEN IN VIVO REACTION
REACTION DIAGRAM
LITERATURE
ENZYME 3D STRUCTURE
L-mandelate + O2 = ? + H2O2
show the reaction diagram
-
(S)-2-hydroxy-2-phenylacetate + tetrahydropteridine + O2 = ?
show the reaction diagram
-

In Vivo Product in Enzyme-catalyzed Reactions (2 results)

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

Substrate in Enzyme-catalyzed Reactions (29 results)

EC NUMBER
REACTION
REACTION DIAGRAM
LITERATURE
ENZYME 3D STRUCTURE
(S)-mandelate + ferricytochrome c = hydroxy(phenyl)acetate + ferrocytochrome c
show the reaction diagram
-
(2S)-hydroxy(phenyl)acetic acid + acceptor = oxo(phenyl)acetic acid + reduced acceptor
show the reaction diagram
-

Product in Enzyme-catalyzed Reactions (11 results)

EC NUMBER
REACTION
REACTION DIAGRAM
LITERATURE
ENZYME 3D STRUCTURE
(R,S)-2-O-butyryl-2-phenylacetate + H2O = (R)-2-O-butyryl-2-phenylacetate + (2S)-hydroxy(phenyl)ethanoic acid + butyrate
show the reaction diagram
-
-
(acetyloxy)(phenyl)acetic acid + H2O = (S)-mandelic acid + (2R)-(acetyloxy)(phenyl)ethanoic acid
show the reaction diagram
-
-
2-hydroxy-2-phenylmalonic acid = (2S)-hydroxy(phenyl)ethanoic acid + CO2
show the reaction diagram
-
-

Inhibitor in Enzyme-catalyzed Reactions (8 results)

EC NUMBER
COMMENTARY
LITERATURE
ENZYME 3D STRUCTURE
competitive
-
competitive
-
competitive
-

3D Structure of Enzyme-Ligand-Complex (PDB) (5 results)

Enzyme Kinetic Parameters

kcat Value (Turnover Number) (78 results)

EC NUMBER
TURNOVER NUMBER [1/S]
TURNOVER NUMBER MAXIMUM [1/S]
COMMENTARY
LITERATURE
1.2
-
at pH 7.5 and 28°C

KM Value (79 results)

EC NUMBER
KM VALUE [MM]
KM VALUE MAXIMUM [MM]
COMMENTARY
LITERATURE
44
-
at pH 7.5 and 28°C
64.9
-
pH 8.0, 30°C
0.1
-
-

Ki Value (10 results)

EC NUMBER
KI VALUE [MM]
KI VALUE MAXIMUM [MM]
COMMENTARY
LITERATURE
8.2
-
pH 9.5, 27°C
0.0026
-
-
11
-
-
2.4
-
in 50 mM Tris-HCl, at 25°C

References & Links

Links to other databases for (S)-mandelic acid

ChEBI
PubChem
ChEBI
PubChem