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BRENDA support

Ligand glycolic acid

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Basic Ligand Information

Molecular Structure
Picture of glycolic acid (click for magnification)
Molecular Formula
BRENDA Name
InChIKey
C2H4O3
glycolic acid
AEMRFAOFKBGASW-UHFFFAOYSA-N
Synonyms:
2-hydroxyacetate, glycolate, hydroxyacetate, hydroxyacetic acid


Show all pahtways known for Show all BRENDA pathways known for glycolic acid

Roles as Enzyme Ligand

In Vivo Substrate in Enzyme-catalyzed Reactions (10 results)

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

In Vivo Product in Enzyme-catalyzed Reactions (63 results)

EC NUMBER
PROVEN IN VIVO REACTION
REACTION DIAGRAM
LITERATURE
ENZYME 3D STRUCTURE
glycolaldehyde + NAD+ + H2O = glycolate + NADH + 2 H+
show the reaction diagram
-
S-glycolyltrypanothione + H2O = glycolate + trypanothione
show the reaction diagram
-
3-oxoisoapionate 4-phosphate + H2O = glycolate + 3-phospho-D-glycerate
show the reaction diagram
-

Substrate in Enzyme-catalyzed Reactions (27 results)

EC NUMBER
REACTION
REACTION DIAGRAM
LITERATURE
ENZYME 3D STRUCTURE
glycolate + ferricytochrome c = glyoxylate + ferrocytochrome c
show the reaction diagram
-
glycolate + ferricytochrome c = ?
show the reaction diagram
-
glycolate + O2 = glyoxylate + H2O2
show the reaction diagram
-
glycolate + 2,6-dichlorophenolindophenol = ?
show the reaction diagram
-
glycolate + O2 + H2O = ?
show the reaction diagram
-
GDP-mannose + glycolic acid = ?
show the reaction diagram
-
ATP + glycolic acid = ADP + ?
show the reaction diagram
-
acetyl-CoA + glycolate = acetate + glycolyl-CoA
show the reaction diagram
-
ATP + glycolate + CoA = ADP + phosphate + glycolyl-CoA
show the reaction diagram
-

Product in Enzyme-catalyzed Reactions (137 results)

EC NUMBER
REACTION
REACTION DIAGRAM
LITERATURE
ENZYME 3D STRUCTURE
glyoxylate + NADPH = glycolate + NADP+
show the reaction diagram
-
glyoxylate + NADPH + H+ = glycolate + NADP+
show the reaction diagram
-
glyoxylate + NAD(P)H = glycolic acid + NAD(P)+
show the reaction diagram
-
4-hydroxyphenoxyacetate + ? = hydroquinone + glycolate + ?
show the reaction diagram
-
glycoaldehyde + NAD+ + H2O = glycolate + NADH
show the reaction diagram
-
glycolaldehyde + NADP+ + H2O = glycolate + NADPH + H+
show the reaction diagram
-
glycolaldehyde + NADP+ + H2O = glycolate + NADPH + H+
show the reaction diagram
-
glycoaldehyde + NAD+ + H2O = glycolate + NADH + H+
show the reaction diagram
-
glycolaldehyde + NADP+ = glycolate + NADPH + H+
show the reaction diagram
-
glycolaldehyde + H2O + O2 = hydroxyacetate + H2O2
show the reaction diagram
-
alpha-ketobutyrate + Fe(CN)63- + H2O = hydroxyacetate + CO2 + Fe(CN)64-
show the reaction diagram
-
glycolaldehyde + ferricyanide = hydroxyacetic acid + ferrocyanide + H+
show the reaction diagram
-
Glycolaldehyde + benzyl viologen = Glycolate + reduced benzyl viologen
show the reaction diagram
-
glycoaldehyde + H2O + benzylviologen = glycolate + reduced benzylviologen
show the reaction diagram
-
methyl hydroxyacetate + H2O = methanol + hydroxyacetate
show the reaction diagram
-
phosphoglycolate + H2O = glycolate + phosphate
show the reaction diagram
-
phosphoglycolate + H2O = glycolate + phosphate
show the reaction diagram
-
N-(phenylacetyl)thioglycylglycolic acid + H2O = phenylacetylglycine + glycolate
show the reaction diagram
-
glycolonitrile + 2 H2O = glycolic acid + NH3
show the reaction diagram
-
glycolonitrile + H2O = glycolic acid + NH3
show the reaction diagram
-
glycolonitrile + 2 H2O = glycolic acid + NH3
show the reaction diagram
-
3-oxoisoapionate 4-phosphate + H2O = glycolate + 3-phospho-D-glycerate
show the reaction diagram
-
monochloroacetic acid + H2O = glycolate + chloride
show the reaction diagram
-
carboxymethyloxysuccinate = fumarate + glycolate
show the reaction diagram
-

Activator in Enzyme-catalyzed Reactions (2 results)

EC NUMBER
COMMENTARY
LITERATURE
ENZYME 3D STRUCTURE
activates, chelates and stabilizes Mn3+
-
0.030 mM
-

Inhibitor in Enzyme-catalyzed Reactions (36 results)

EC NUMBER
COMMENTARY
LITERATURE
ENZYME 3D STRUCTURE
18% inhibition at 17 mM
-
5 mM, 15% of NADPH linked reduction
-
tyrosinase inhibitor
-
substrate inhibition
-
20 mM, more than 60% inhibition
-
50% activity loss with 0.06 mM glycolate for 10 min at 30°C; strong inhibitor, 50% inhibition at 0.06 mM
-
88% residual activity at 20 mM
-
glycolic acid inhibits the enzyme competitively with respect to formaldehyde
-
in direction of malyl-CoA synthesis: competitive with respect to glyoxylate and noncompetitive with respect to acetyl-CoA.In direction of malyl-CoA cleavage: competitive with respect to malyl-CoA
-
weak
-
30% inhibition at 1 mM
-

3D Structure of Enzyme-Ligand-Complex (PDB) (178 results)

EC NUMBER
ENZYME 3D STRUCTURE

Enzyme Kinetic Parameters

kcat Value (Turnover Number) (13 results)

EC NUMBER
TURNOVER NUMBER [1/S]
TURNOVER NUMBER MAXIMUM [1/S]
COMMENTARY
LITERATURE
0.00167
-
-
1.93
-
with 2,6-dichlorophenolindophenol as cosubstrate, at pH 8.0 and 30°C
0.0052
-
pH 7.8, 25°C, cosubstrate: GDP-mannose

KM Value (38 results)

EC NUMBER
KM VALUE [MM]
KM VALUE MAXIMUM [MM]
COMMENTARY
LITERATURE
0.432
-
-
167
-
at pH 5.5 and 30°C
23.7
-
pH 7.8, 25°C, cosubstrate: GDP-mannose

Ki Value (18 results)

EC NUMBER
KI VALUE [MM]
KI VALUE MAXIMUM [MM]
COMMENTARY
LITERATURE
28
-
in citrate buffer, at pH 4.0 and 22°C

IC50 Value (2 results)

EC NUMBER
IC50 VALUE
IC50 VALUE MAXIMUM
COMMENTARY
LITERATURE
58
-
apparent value, at pH 8.0, temperature not specified in the publication
58
-
pH 8.0, temperature not specified in the publication

References & Links

Links to other databases for glycolic acid

ChEBI
PubChem
ChEBI
PubChem