Ligand thioglycolic acid

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Basic Ligand Information

Molecular Structure
Picture of thioglycolic acid (click for magnification)
Molecular Formula
BRENDA Name
InChIKey
C2H4O2S
thioglycolic acid
CWERGRDVMFNCDR-UHFFFAOYSA-N
Synonyms:
2-mercaptoacetate, 2-mercaptoacetic acid, 2-thioacetate, beta-mercaptoacetate, carboxymethylthiol, HS-CH2-COOH, Mercaptoacetate, Mercaptoacetic acid, thioglycolate, Thioglycollate, Thioglycollic acid, thiolglycolic acid
Pathway Source
Pathways

Roles as Enzyme Ligand

Substrate in Enzyme-catalyzed Reactions (12 results)

EC NUMBER
REACTION
REACTION DIAGRAM
LITERATURE
ENZYME 3D STRUCTURE
thioglycolate + O2 = ? + H2O
show the reaction diagram
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thioglycolic acid + protein disulfide = ?
show the reaction diagram
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O-acetyl-L-Ser + mercaptoacetic acid = S-carboxymethyl-L-cysteine
show the reaction diagram
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O-acetyl-L-homoserine + thioglycolic acid = ?
show the reaction diagram
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L-homoserine + thioglycolate = S-carboxymethyl-L-homocysteine
show the reaction diagram
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L-Cys + thioglycolate = ?
show the reaction diagram
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3-chloro-D-alanine + thioglycolic acid = S-carboxymethyl-D-cysteine
show the reaction diagram
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3-chloro-L-alanine + thioglycolate = S-carboxymethyl-L-cysteine + Cl-
show the reaction diagram
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ATP + thioglycolate + CoA = ADP + phosphate + thioglycolyl-CoA
show the reaction diagram
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ATP + thioglycolate + CoA = ADP + phosphate + thioglycolyl-CoA
show the reaction diagram
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Product in Enzyme-catalyzed Reactions (5 results)

EC NUMBER
REACTION
REACTION DIAGRAM
LITERATURE
ENZYME 3D STRUCTURE
hippuryl-mercaptoacetic acid = hippuric acid + mercaptoacetate
show the reaction diagram
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-
S-carboxymethyl-D-cysteine + H2O = mercaptoacetic acid + pyruvate + NH3
show the reaction diagram
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Activator in Enzyme-catalyzed Reactions (15 results)

EC NUMBER
COMMENTARY
LITERATURE
ENZYME 3D STRUCTURE
thiol compound required
-
activation
-
activates at 0.01 M
-
1 mM, activation, inhibition at 5 mM
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greater reactivation at 33 mM than at 3.3 mM
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1.0 mM, relative activity 101%
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stimulation
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reduction is essential for catalytic activity
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activates, synergistic with EDTA
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maximal activity in presence of various reducing compounds, e.g. Cys, 2,3-dimercaptopropanol, thioglycolic acid, glutathione
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increase of activity
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sulfhydryl compound is required for maximal activity
-
best activator among sulfhydryl reagents
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Inhibitor in Enzyme-catalyzed Reactions (47 results)

EC NUMBER
COMMENTARY
LITERATURE
ENZYME 3D STRUCTURE
competitive
-
96% inhibition at 10 mM
-
inhibition by administration in vivo
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weak
-
74% inhibition
-
slight
-
60% loss of activity at 10 mM
-
Zn2+ reverses, bovine serum albumin as substrate
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5 mM, isoform LeARG1, 28% residual activity, LeARG2, 26% residual activity; 5 mM, isoform LeARG1, 28% residual activity, LeARG2, 26% residual activity
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strong mixed-type inhibitor
-
0.7 mM 88% relative activity, complete inhibition at 7 mM
-
competitive
-
weak
-
weak
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3D Structure of Enzyme-Ligand-Complex (PDB) (26 results)

Enzyme Kinetic Parameters

kcat Value (Turnover Number) (2 results)

EC NUMBER
TURNOVER NUMBER [1/S]
TURNOVER NUMBER MAXIMUM [1/S]
COMMENTARY
LITERATURE
26.1
-
at pH 6.5 and 55°C
-999
-
pH 6.5, 55°C, kinetic constant according to Adair-Pauling kinetic model: 26.1/s

KM Value (4 results)

EC NUMBER
KM VALUE [MM]
KM VALUE MAXIMUM [MM]
COMMENTARY
LITERATURE
0.19
-
-
15.4
-
pH 7.8, 37°C
0.322
-
at pH 6.5 and 55°C
-999
-
pH 6.5, 55°C, kinetic constant according to Adair-Pauling kinetic model: 0.322 mM

Ki Value (1 result)

EC NUMBER
KI VALUE [MM]
KI VALUE MAXIMUM [MM]
COMMENTARY
LITERATURE
0.802
-
pH 4.5, 25°C

References & Links

Links to other databases for thioglycolic acid

ChEBI
PubChem
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PubChem