Ligand glycolaldehyde

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Basic Ligand Information

Molecular Structure
Picture of glycolaldehyde (click for magnification)
Molecular Formula
BRENDA Name
InChIKey
C2H4O2
glycolaldehyde
WGCNASOHLSPBMP-UHFFFAOYSA-N
Synonyms:
2-hydroxyacetaldehyde, glycoaldehyde, Hydroxyacetaldehyde


Show all pahtways known for Show all BRENDA pathways known for glycolaldehyde

Roles as Enzyme Ligand

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

EC NUMBER
PROVEN IN VIVO REACTION
REACTION DIAGRAM
LITERATURE
ENZYME 3D STRUCTURE
6-hydroxymethyl-7,8-dihydropterin + glycolaldehyde = 7,8-dihydroneopterin + 7,8-dihydromonapterin
show the reaction diagram
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glycine + glycolaldehyde = L-4-hydroxythreonine
show the reaction diagram
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In Vivo Product in Enzyme-catalyzed Reactions (6 results)

EC NUMBER
PROVEN IN VIVO REACTION
REACTION DIAGRAM
LITERATURE
ENZYME 3D STRUCTURE
7,8-dihydroneopterin + O2 = 7,8-dihydroxanthopterin + formate + glycolaldehyde
show the reaction diagram
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ethanolamine + H2O + O2 = glycolaldehyde + NH3 + H2O2
show the reaction diagram
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Substrate in Enzyme-catalyzed Reactions (77 results)

EC NUMBER
REACTION
REACTION DIAGRAM
LITERATURE
ENZYME 3D STRUCTURE
glycolaldehyde + NADH + H+ = glycol + NAD+
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glycolaldehyde + NADPH = ethane-1,2-diol + NADP+
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glycoaldehyde + NADPH + H+ = ?
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glycolaldehyde + NADPH = ethyleneglycol + NADP+
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glycolaldehyde + nitro blue tetrazolium = ? + reduced nitro blue tetrazolium
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glycolaldehyde + CoA + NAD+ = hydroxyacetyl-CoA + NADH
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glycoaldehyde + NAD+ + H2O = glycolate + NADH
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glycolaldehyde + NADP+ + H2O = glycolate + NADPH + H+
show the reaction diagram
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glycolaldehyde + NADP+ + H2O = glycolate + NADPH + H+
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glycoaldehyde + NAD+ + H2O = glycolate + NADH + H+
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glycolaldehyde + coenzyme A + NADP+ = ? + NADPH + H+
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glycolaldehyde + NADP+ = glycolate + NADPH + H+
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glycolaldehyde + O2 + H2O = ?
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glycolaldehyde + ferricyanide = hydroxyacetic acid + ferrocyanide + H+
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Glycolaldehyde + benzyl viologen = Glycolate + reduced benzyl viologen
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glycoaldehyde + H2O + benzylviologen = glycolate + reduced benzylviologen
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pyruvate + glycolaldehyde = 1-deoxy-L-erythrulose + CO2
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L-threonine + glycolaldehyde = acetaldehyde + 4-hydroxyl-L-threonine
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phosphoenolpyruvate + glycolaldehyde = (S)-2-oxo-4,5-dihydroxypentanoate + phosphate
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taurine + glycolaldehyde = 2-sulfoacetaldehyde + ?
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beta-hydroxypyruvate + glycolaldehyde = 1,3,4-trihydroxy-2-butanone
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pyruvate + glycoaldehyde = ?
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Glycerone phosphate + glycolaldehyde = L-Xylulose 1-phosphate
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pyruvate + glycolaldehyde = 2-oxo-4,5-dihydroxy-L-pentanoic acid
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6-hydroxymethyl-7,8-dihydropterin + glycolaldehyde = 7,8-dihydroneopterin + 7,8-dihydromonapterin
show the reaction diagram
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glycine + glycolaldehyde = L-4-hydroxythreonine
show the reaction diagram
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pyruvate + glycolaldehyde = ?
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pyruvate + glycolaldehyde = ?
show the reaction diagram
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pyruvate + glycolaldehyde = ?
show the reaction diagram
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glycolaldehyde = ?
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Product in Enzyme-catalyzed Reactions (35 results)

EC NUMBER
REACTION
REACTION DIAGRAM
LITERATURE
ENZYME 3D STRUCTURE
1,2-ethanediol + NADP+ = hydroxyacetaldehyde + NADPH
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glyoxal + NADPH = glycolaldehyde + NADP+
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ethanediol + NAD+ = glycolaldehyde + NADH
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ethylene glycol + NAD+ = glycolaldehyde + NAD+
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glyoxal + NADH = glycolaldehyde + NAD+
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1,2-ethanediol + ferricyanide = hydroxyacetaldehyde + ferrocyanide
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7,8-dihydroneopterin + O2 = 7,8-dihydroxanthopterin + formate + glycolaldehyde
show the reaction diagram
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isethionate + FMNH2 + O2 = hydroxyacetaldehyde + FMN + sulfite + H2O
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ethanolamine + H2O + O2 = glycolaldehyde + NH3 + H2O2
show the reaction diagram
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ethanolamine + H2O + O2 = glycolaldehyde + NH3 + H2O2
show the reaction diagram
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ethanolamine + H2O + O2 = glycolaldehyde + NH3 + H2O2
show the reaction diagram
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laminarin + H2O = glycerol + glycoaldehyde + D-glucose
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Hydroxypyruvate = Glycolaldehyde + CO2
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D-ribose 1-phosphate = glycerone phosphate + glycolaldehyde
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Xylulose 1-phosphate = Glycerone phosphate + glycoaldehyde
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2-dehydro-3-deoxy-D-pentonate = pyruvate + glycolaldehyde
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Glyceraldehyde phosphate + acetaldehyde = Hydroxyacetaldehyde + glyceraldehyde 3-phosphate
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L-4-hydroxythreonine = glycine + glycolaldehyde
show the reaction diagram
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Inhibitor in Enzyme-catalyzed Reactions (10 results)

EC NUMBER
COMMENTARY
LITERATURE
ENZYME 3D STRUCTURE
substrate inhibition
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substrate inhibition
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weak
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49% inhibition at 4 mM
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competitive, Ki for 2-keto-4-hydroxybutyrate cleavage: 2.7 mM, Ki for 2-keto-4-hydroxyglutarate cleavage: 2.4 mM
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about 60% inhibition at 10 mM
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inactivates
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3D Structure of Enzyme-Ligand-Complex (PDB) (1 result)

EC NUMBER
ENZYME 3D STRUCTURE

Enzyme Kinetic Parameters

kcat Value (Turnover Number) (14 results)

EC NUMBER
TURNOVER NUMBER [1/S]
TURNOVER NUMBER MAXIMUM [1/S]
COMMENTARY
LITERATURE
18.65
-
pH 7.0, 30°C
18.3
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100 mM H2NaPO4 pH 7.5, 100 mM NaCl, 20 mM 2-mercaptoethanol, 2 mM NAD+
5.3
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pH 7.5, 70°C
1.2
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0.024
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at pH 7.5 and 28°C
175.5
-
Kcat(app) with pyruvate as carbonyl donor, pH 8.0 and 25°C
0.4
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app. kcat-value with pyruvate as carbonyl donor, pH 8.0 and 25°C

KM Value (51 results)

EC NUMBER
KM VALUE [MM]
KM VALUE MAXIMUM [MM]
COMMENTARY
LITERATURE
88.32
-
pH 7.0, 30°C
9.9
-
AR2
13.2
-
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20
-
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0.37
-
pH 6.0, 70°C, native enzyme form xylose-grown cells
2.2
-
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0.15
-
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1
-
pH 7.0, 30°C
0.357
-
at pH 7.5 and 28°C
8.6
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cytosolic isozyme DS-Co, pH 8.6, 37°C
10
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apparent value
33.3
-
Km(app) with pyruvate as carbonyl donor, pH 8.0 and 25°C
124.6
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app. Km-value with pyruvate as carbonyl donor, pH 8.0 and 25°C

Ki Value (4 results)

EC NUMBER
KI VALUE [MM]
KI VALUE MAXIMUM [MM]
COMMENTARY
LITERATURE
0.37
-
37°C, pH 7.6, mutant enzyme H97N, with L-ribulose 5-phosphate as substrate

References & Links

Links to other databases for glycolaldehyde

ChEBI
PubChem
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PubChem