Ligand glyoxylic acid

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Basic Ligand Information

Molecular Structure

C₂H₂O₃

glyoxylic acid

HHLFWLYXYJOTON-UHFFFAOYSA-N

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Synonyms:

CHO-COOH, glyocylate, glyoxalate, glyoxalic acid, glyoxylate, oxoacetic acid

Related pathways

BRENDA

allantoin degradation, citric acid cycle, ethylmalonyl-CoA pathway, gluconeogenesis, glycine metabolism

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KEGG

Arginine and proline metabolism, Biosynthesis of secondary metabolites, C5-Branched dibasic acid metabolism, Caffeine metabolism, Carbon fixation pathways in prokaryotes

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MetaCyc

2,4,5-trichlorophenoxyacetate degradation, 2,4-dichlorophenoxyacetate degradation, 3-hydroxypropanoate cycle, 4-chloro-2-methylphenoxyacetate degradation, allantoin degradation to glyoxylate I

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Show all BRENDA pathways known for glyoxylic acid

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Roles as Enzyme Ligand

In Vivo Substrate in Enzyme-catalyzed Reactions (60 results)

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glyoxylic acid + O2 + H2O = oxalate + H2O2

288396, 288397, 724143

1.4.1.1

glyoxylate + NH3 + NADH + H+ = glycine + H2O + NAD+

762684

1.4.1.10

glyoxylate + NH3 + NADH = glycine + H2O + NAD+

propanoyl-CoA + glyoxylate = 2-hydroxyglutarate + CoA

488127, 488124, 488125

2.3.3.7

butanoyl-CoA + H2O + glyoxylate = 3-ethylmalate + CoA

488180, 488129, 488126

glyoxylate + L-aspartate = glycine + oxaloacetate

639968, 639967, 639966

2.6.1.4

glyoxylate + L-glutamate = glycine + 2-oxoglutarate

639986, 639988, 636731, 639991, 639987

an aromatic amino acid + glyoxylate = an aromatic oxo acid + glycine

4-aminobutanoate + glyoxylate = succinate semialdehyde + glycine

704874, 720325, 704882

In Vivo Product in Enzyme-catalyzed Reactions (57 results)

nitrilotriacetate + FMNH2 + H+ + O2 = iminodiacetate + glyoxylate + FMN + H2O

1.14.14.33

ethylenediaminetetraacetate + 2 FMNH2 + 2 O2 = ethylenediamine-N,N'-diacetate + 2 glyoxylate + 2 FMN + 2 H2O

1.14.17.3

2 entries

1.2.3.15

glyoxal + H2O + O2 = glyoxylate + H2O2

1.4.1.1

glycine + H2O + NAD+ = glyoxylate + NH3 + NADH + H+

1.4.2.1

glycine + ferricytochrome c = glyoxylate + ferrocytochrome c + NH3

Gly + H2O + O2 = glyoxylate + NH3 + H2O2

3.5.1.116

3 entries

3.5.3.9

allantoate + 3 H2O = glyoxylate + 4 NH3 + 2 CO2

4.1.3.1

14 entries

4.1.3.16

4-Hydroxy-2-oxoglutarate = Pyruvate + glyoxylate

Substrate in Enzyme-catalyzed Reactions (364 results)

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1.1.1.215

glyoxylate + NADPH = glycolate + NADP+

286273

1.1.1.237

glyoxylate + NADPH + H+ = glycolate + NADP+

glyoxylate + NADH + H+ = 2-hydroxypropanoate + NAD+

719359

1.1.1.428

glyoxylate + NADH + H+ = ?

764063

1.1.1.71

glyoxylic acid + NADPH + H+ = ? + NADP+

glyoxylate + NAD(P)H = glycolic acid + NAD(P)+

glyoxylate + O2 = oxalate + H2O2

746024

1.1.99.14

glyoxylate + acceptor = oxalate + reduced acceptor

348285, 348286

1.17.1.9

glyoxylate + NAD+ = ? + NADH

glyoxylate + NADH = glyoxal + NAD+

390215

1.2.1.24

glyoxylic acid + NAD+ + H2O = 2-phenylbenzoate + NADH + H+

700082

1.2.1.88

glyoxylic acid + NAD+ + H2O = oxalic acid + NADH

392065

1.2.3.13

glyoxylate + O2 = CO2 + CO2

288040

1.2.3.15

glyoxylic acid + H2O + O2 = ?

738490, 739561, 763111

1.2.3.4

2 entries

1.2.3.5

glyoxylic acid + O2 + H2O = oxalate + H2O2

288396, 288397, 724143

1.2.7.1

glyoxylate + CoA + 2 oxidized methyl viologen = ?

673610

1.2.7.10

glyoxylate + methyl viologen = ?

715568

1.2.7.11

glyoxylate + CoA + 2 oxidized methyl viologen = formyl-CoA + CO2 + 2 reduced methyl viologen + 2 H+

673610

1.2.7.7

glyoxylate + CoA + oxidized ferredoxin = formyl-CoA + CO2 + reduced ferredoxin

644696

1.2.99.6

glyoxylate + benzyl viologen = oxalic acid + reduced benzyl viologen

L-Arg + glyoxylate + NADPH = ?

13323

1.5.1.17

L-Ala + glyoxylate + NADH = ?

13374, 13370, 13365

1.5.1.22

3 entries

1.5.1.23

Taurine + glyoxylate + NADH = ?

13437, 13439, 13440

1.5.1.24

L-ornithine + glyoxylic acid + NADPH + H+ = ? + NADP+ + H2O

712294

1.5.1.25

glyocylate + methylamine + NADPH + H+ = sarcosine + NADP+

741584

1.5.1.28

L-Met + glyoxylate + NADH = ?

94167

1.5.1.52

(2S)-2-amino-4-[[(1R)-1-carboxy-2-(1H-imidazol-4-yl)ethyl]amino]butanoate + glyoxylate + NADPH + H+ = ? + NADP+ + H2O

748236

1.5.1.7

L-lysine + glyoxylate + NADH = ?

685171

1.5.1.B8

(2S)-2-amino-4-([(1S)-1-carboxy-2-(1H-imidazol-4-yl)ethyl]amino)butanoate + glyoxylate + NADPH + H+ = ? + NADP+ + H2O

glyoxylate + 2-oxoglutarate = 5-hydroxy-4-oxopentanoic acid + 2 CO2

pentanoyl-CoA + glyoxylate + H2O = 3-propylmalate + CoA

488126, 488128, 488129

2.3.3.21

acetyl-CoA + glyoxylate + H2O = ?

685015

2.3.3.7

butanoyl-CoA + H2O + glyoxylate = 3-ethylmalate + CoA

488180, 488129, 488126

2.3.3.9

35 entries

2.5.1.54

phosphoenolpyruvate + glyoxylate = S-4-hydroxy-2-oxo-1,5-pentanedioate + R-4-hydroxy-2-oxo-1,5-pentanedioate + phosphate

639780

2.6.1.112

(S)-ureidoglycine + glyoxylate = N-carbamoyl-2-oxoglycine + glycine

741043

2.6.1.116

6-aminohexanoate + glyoxylate = 6-oxohexanoate + glycine

752570

2.6.1.12

L-alanine + glyoxylate = pyruvate + glycine

636593

2.6.1.13

L-ornithine + glyoxylate = DELTA1-pyrroline-5-carboxylate + glycine

637103, 637098, 637126, 637111, 637130

4-aminobutanoate + glyoxylate = 4-oxobutanoate + glycine

637056, 704882, 704874, 723611

2.6.1.2

8 entries

2.6.1.27

L-tryptophan + glyoxylate = 3-indole-2-oxopropanoate + glycine

L-histidine + glyoxylate = imidazol-5-yl-pyruvate + glycine

(R)-3-amino-2-methylpropanoate + glyoxylate = 2-methyl-3-oxopropanoate + glycine

644426, 644428, 644430, 644431, 636964

L-glutamine + glyoxalate = 2-oxoglutaramate + glycine

L-phenylalanine + glyoxylate = phenylpyruvate + glycine

glyoxylate + (S)-(-)-1-phenylethylamine = ?

taurine + glyoxylate = 2-sulfoacetaldehyde + glycine

737516

2.6.1.78

glyoxylate + L-aspartate = glycine + oxaloacetate

L-alanine + glyoxylate = pyruvate + glycine

Pyruvate + glyoxylate = ?

4971

4.1.2.55

Pyruvate + glyoxylate = ?

Oxaloacetate + glyoxylate = 3-Oxalomalate

pyruvate + glyoxylate = 4-hydroxy-2-oxoglutarate

ATP + glyoxalate + CoA = ?

654636

Product in Enzyme-catalyzed Reactions (237 results)

glycolate + ferricytochrome c = glyoxylate + ferrocytochrome c

1.1.3.13

glycolate + O2 = glyoxylate + H2O2

glycine + O2 = oxoacetic acid + NH3

1.14.12.11

trichloroethylene + O2 + NADPH = formate + glyoxylate + NADP+

oxalate + NADH = glyoxylate + NAD+

390215

1.2.1.46

glyoxal + NAD+ + H2O = glyoxylate + NADH

1.2.1.65

glyoxal + NAD+ + H2O = glyoxylate + NADH + H+

1.2.3.1

glyoxal + H2O + O2 = glyoxylate + H2O2

1.2.3.15

glyoxal + H2O + O2 = glyoxylate + H2O2

1.2.5.2

glyoxal + ferricyanide = oxoacetic acid + ferrocyanide + H+

glycine + H2O + O2 = glyoxylate + NH3 + H2O2

1.5.3.20

3 entries

1.5.3.23

2 glyphosate + O2 = 2 aminomethylphosphonate + 2 glyoxylate

2.2.1.1

2 hydroxypyruvate = 2 glyoxylic acid + erythrulose

2.5.1.18

dichloroacetate + glutathione = glyoxylate + HCl + ?

2.6.1.1

glycine + 2-oxoglutarate = glyoxylate + L-glutamate

2.6.1.15

2-oxoglutaramate + glycine = L-glutamine + glyoxylate

639898

2.6.1.18

pyruvate + glycine = L-alanine + glyoxylate

288059

2.6.1.2

glycine + 2-oxoglutarate = glyoxylate + glutamate

636718

2.6.1.33

dTDP-4-dehydro-6-deoxy-D-glucose + glycine = dTDP-4-amino-4,6-dideoxy-D-galactose + glyoxylate

2.6.1.40

glycine + pyruvate = glyoxylate + L-alanine

2.6.1.42

2 entries

2.6.1.43

glycine + 4,5-dioxopentanoate = 5-aminolevulinate + glyoxylate

glycine + 2-oxoglutarate = glyoxalate + L-glutamate

2.6.1.51

3 entries

2.6.1.B16

pyruvate + glycine = L-alanine + glyoxylate

(-)-ureidoglycolate = glyoxylate + urea

172151, 172154, 172149, 172142, 172152, 172153, 172137, 34475, 172139, 172140, 172150, 246655, 34473, 34471, 172141, 172147, 172143, 172144, -

3.5.3.9

allantoate + 3 H2O = glyoxylate + 4 NH3 + 2 CO2

chlorofluoroacetic acid + ? = glyoxylate + ?

Activator in Enzyme-catalyzed Reactions (4 results)

50 mM, increasing enzyme activity by 30%

activates

Inhibitor in Enzyme-catalyzed Reactions (121 results)

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1.1.1.154

non-competitive inhibition, Ki: 83 mM

287162, 287165, 287166

strain CETC 978, competitive inhibition

2-oxoglutarate dehydrogenase complex

349020, 349030

1.2.1.15

competitive inhibitor

1 mM, 33% inhibition

20 mM, about 40% of the original activity is lost. 2 mM glyoxylate inhibits 6%

weak

5 mM, 30% inhibition of reductive amination

391513

1.4.1.4

at 20 mM, 30% inhibition

20 mM, more than 60% inhibition

inhibitor of octopine formation

weak

isozyme AHAS II

competitive, analysis of pH-dependence of inhibition

alpha-keto acid acceptor, inhibitor at high concentrations

637098, 637107

2.6.1.15

at high concentration, transamination between albizziin and glyoxylate

weak

at high concentrations

5 mM, 79% of activity remaining; 5 mM, 83% of activity remaining

isoenzyme II, french bean

35343

3.1.3.43

at concentrations greater than 0.05 mM

50% activity loss with 0.02 mM glycolate for 10 min at 30°C; strong inhibitor, 50% inhibition at 0.02 mM

7.2% residual activity at 8 mM

748094

4.1.2.43

12% inhibition at 4 mM

691118

4.1.2.52

competitive inhibition

competitive inhibition

702377

4.2.1.130

determmination of an enzyme crystal structure with the inhibitor bound to the active Cys residue of the enzyme as a hemithioacetal, detailed binding structure analysis, overview

20 mM: 54.1% inhibition, not reversed by 5 mM AMP

20 mM, 27% inhibition

32% residual activity at 10 mM

744820

6.2.1.B11

inhibits the activity in the acetate-forming direction

3D Structure of Enzyme-Ligand-Complex (PDB) (222 results)

Enzyme Kinetic Parameters

k_cat Value (Turnover Number) (118 results)

pH 6.5, 25°C

0.0133

pH 6.9, 85°C, under argon

644696

1.5.1.52

0.074

pH 8.0, 22°C

748236

1.5.1.B8

0.22

recombinant enzyme, with NADPH and L-histidine nicotianamine, pH 8.0, 22°C

748236

2.2.1.5

5.29

at pH 6.5 and 37°C

48.2

pH 7.5, 30°C

113

3.6

pH 7.5, 25°C, recombinant enzyme

727039

K_M Value (294 results)

0.38

18.9

pH 6.5, 25°C

pH 8.0, 70°C

isoform A

3.7

8.8

L-Met and NADH as cosubstrate

pH 8.0, 22°C

6.4

at pH 7.0

685171

1.5.1.B8

1.9

recombinant enzyme, with NADPH and L-histidine nicotianamine, pH 8.0, 22°C

3.6

cytosolic isozyme DS-Co, pH 8.6, 37°C

639780

2.6.1.13

6.7

pH 7.1, 37°C

637098

2.6.1.14

0.077

cosubstrate L-asparagine

pH 8.4, 37ºC

0.43

pH 7.1, 25°C, with substrate L-aspartate

7.04

pH 7.0, 22°C

0.43

14.3

K_i Value (30 results)

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1.1.1.28

pH 7.0, 30°C, recombinant enzyme

739841

1.1.1.40

0.6

at pH 7.5 and 33°C

0.01

1.8

0.27

pH 7.0, 20°C

739954

1.2.3.4

in citrate buffer, at pH 4.0 and 22°C

724114

2.2.1.5

53.1

at pH 6.5 and 37°C

736420

2.3.3.14

0.4

pH 7.2

672072

2.6.1.43

0.5

pH 8.0, 37°C

640050

2.6.1.45

0.4

pH 8.1, 30°C

636689

4.1.2.52

0.4

pH 8.0, 25°C

702377

4.1.3.1

4.3

recombinant detagged enzyme, pH 7.0, 37°C

0.21

pH 8.0, 25°C

702377

4.2.1.130

0.14

pH and temperature not specified in the publication

0.04

IC₅₀ Value (1 result)

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4.1.2.22

1.93

at pH 6.0 and 37°C

748094

References & Links

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Show Reference (656 entries)

Links to other databases for glyoxylic acid

Ligand glyoxylic acid

Basic Ligand Information

Related pathways

Roles as Enzyme Ligand

In Vivo Substrate in Enzyme-catalyzed Reactions (60 results)

In Vivo Product in Enzyme-catalyzed Reactions (57 results)

Substrate in Enzyme-catalyzed Reactions (364 results)

Product in Enzyme-catalyzed Reactions (237 results)

Activator in Enzyme-catalyzed Reactions (4 results)

Inhibitor in Enzyme-catalyzed Reactions (121 results)

3D Structure of Enzyme-Ligand-Complex (PDB) (222 results)

Enzyme Kinetic Parameters

kcat Value (Turnover Number) (118 results)

KM Value (294 results)

Ki Value (30 results)

IC50 Value (1 result)

References & Links

Literature References (656)

Links to other databases for glyoxylic acid

k_cat Value (Turnover Number) (118 results)

K_M Value (294 results)

K_i Value (30 results)

IC₅₀ Value (1 result)