Ligand L-glutamine

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Basic Ligand Information

Molecular Structure
Picture of L-glutamine (click for magnification)
Molecular Formula
BRENDA Name
InChIKey
C5H10N2O3
L-glutamine
ZDXPYRJPNDTMRX-VKHMYHEASA-N
Synonyms:
(2S)-2,5-diamino-5-oxopentanoic acid, D-(or L-)glutamine, Gln, glutamine, L-Gln

Show all pahtways known for Show all pathways known for L-glutamine

Roles as Enzyme Ligand

In Vivo Substrate in Enzyme-catalyzed Reactions (68 results)

EC NUMBER
PROVEN IN VIVO REACTION
REACTION DIAGRAM
LITERATURE
ENZYME 3D STRUCTURE
L-glutamine + 2-oxoglutarate + NADPH = L-glutamate + NADP+
show the reaction diagram
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L-glutamine + 2-oxoglutarate + NADH = glutamate + NAD+
show the reaction diagram
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L-glutamine + H2O + O2 = 2-oxo-4-carbamoylbutanoic acid + NH3 + H2O2
show the reaction diagram
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L-glutamine + 2-oxoglutarate + reduced ferredoxin = L-glutamate + oxidized ferredoxin
show the reaction diagram
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phenylacetyl-CoA + L-glutamine = CoA + alpha-N-phenylacetyl-L-glutamine
show the reaction diagram
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4-hydrazinobenzoic acid + L-glutamine = beta-N-(gamma-L-glutamyl)-4-carboxyphenylhydrazine
show the reaction diagram
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L-glutamine + 2-deoxy-scyllo-inosose = 2-oxoglutaramate + 2-deoxy-scyllo-inosamine
show the reaction diagram
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L-glutamine + 3-amino-2,3-dideoxy-scyllo-inosose = 2-oxoglutaramate + 2-deoxystreptamine
show the reaction diagram
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L-glutamine + D-fructose 6-phosphate = L-glutamate + D-glucosamine 6-phosphate
show the reaction diagram
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L-glutamine + phenylpyruvate = 2-oxoglutaramate + L-phenylalanine
show the reaction diagram
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chorismate + L-glutamine = 4-amino-4-deoxychorismate + L-glutamate
show the reaction diagram
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chorismate + L-glutamine = (2S)-2-amino-4-deoxychorismate + L-glutamate
show the reaction diagram
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L-glutamine + 7-cyano-7-carbaguanine15 in tRNA + H2O = L-glutamate + archaeine15 in tRNA
show the reaction diagram
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L-glutamine + H2O = L-glutamate + NH3
show the reaction diagram
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ATP + H2O + L-Gln/out = ADP + phosphate + L-Gln/in
show the reaction diagram
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ATP + H2O + glutamine/out = ADP + phosphate + glutamine/in
show the reaction diagram
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D-ribose 5-phosphate + D-glyceraldehyde 3-phosphate + L-glutamine = pyridoxal 5'-phosphate + L-glutamate + 3 H2O + phosphate
show the reaction diagram
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ATP + deamido-NAD+ + glutamine = AMP + diphosphate + glutamate + NAD+
show the reaction diagram
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ATP + deamido-NAD+ + L-glutamine + H2O = AMP + diphosphate + NAD+ + L-glutamate
show the reaction diagram
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ATP + Ni-sirohydrochlorin + L-glutamine + H2O = ADP + phosphate + Ni-sirohydrochlorin a,c-diamide + L-glutamate
show the reaction diagram
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In Vivo Product in Enzyme-catalyzed Reactions (11 results)

EC NUMBER
PROVEN IN VIVO REACTION
REACTION DIAGRAM
LITERATURE
ENZYME 3D STRUCTURE
2 L-glutamate + NAD+ = L-glutamine + 2-oxoglutarate + NADH + H+
show the reaction diagram
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2 L-glutamate + 2 oxidized ferredoxin = L-glutamine + 2-oxoglutarate + 2 reduced ferredoxin + 2 H+
show the reaction diagram
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5-phospho-beta-D-ribosylamine + diphosphate + L-glutamate = L-glutamine + 5-phospho-alpha-D-ribose 1-diphosphate + H2O
show the reaction diagram
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ATP + H2O + L-Gln/out = ADP + phosphate + L-Gln/in
show the reaction diagram
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ATP + H2O + glutamine/out = ADP + phosphate + glutamine/in
show the reaction diagram
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Substrate in Enzyme-catalyzed Reactions (303 results)

EC NUMBER
REACTION
REACTION DIAGRAM
LITERATURE
ENZYME 3D STRUCTURE
glutamine + a quinone = ? + a quinol
show the reaction diagram
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L-glutamine + H2O + NAD+ = 2-oxoglutaramate + NH3 + NADH
show the reaction diagram
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L-glutamine + H2O + O2 = ?
show the reaction diagram
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L-Gln + pyruvate + NADPH = N2-(D-1-Carboxyethyl)-L-Gln + NADP+ + H2O
show the reaction diagram
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methylamine + L-glutamine = ?
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phenylacetyl-CoA + L-glutamine = CoA + alpha-N-phenylacetyl-L-glutamine
show the reaction diagram
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L-glutamine + D-glutamic acid = NH3 + gamma-L-glutamyl-D-glutamate
show the reaction diagram
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L-glutamine + KCN = ?
show the reaction diagram
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L-glutamine + 2-deoxy-scyllo-inosose = 2-oxoglutaramate + 2-deoxy-scyllo-inosamine
show the reaction diagram
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L-glutamine + 3-amino-2,3-dideoxy-scyllo-inosose = 2-oxoglutaramate + 2-deoxystreptamine
show the reaction diagram
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glyoxylate + glutamine = glycine + 2-oxosuccinamate
show the reaction diagram
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dTDP-4-dehydro-6-deoxy-D-glucose + L-glutamine = dTDP-4-amino-4,6-dideoxy-D-galactose + 2-oxoglutamine
show the reaction diagram
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glyoxylate + L-glutamine = glycine + 2-oxoglutaramate
show the reaction diagram
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L-glutamine + 2-oxoglutarate = 2,5-dioxo-5-aminopentanoate + L-glutamate
show the reaction diagram
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L-glutamine + 4,5-dioxopentanoate = 5-aminolevulinate + 2-oxoglutaramate
show the reaction diagram
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L-glutamine + 1D-1-guanidino-1-deoxy-3-dehydro-scyllo-inositol = alpha-ketoglutaramate + 1D-1-guanidino-3-amino-1,3-dideoxy-scyllo-inositol
show the reaction diagram
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L-glutamine + phenylpyruvate = 5-amino-2,5-dioxopentanoic acid + L-phenylalanine
show the reaction diagram
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dTDP-4-dehydro-6-deoxy-D-glucose + L-glutamine = dTDP-4-amino-4,6-dideoxy-D-galactose + 2-oxoglutaramate
show the reaction diagram
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glutamine + glyoxylate = 4-carbamoyl-2-oxobutanoate + glycine
show the reaction diagram
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3-(imidazol-4-yl)-2-oxopropyl phosphate + L-glutamine = L-histidinol phosphate + 4-carbamoyl-2-oxobutanoate
show the reaction diagram
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L-glutamine + 7-cyano-7-carbaguanine15 in tRNA + H2O = L-glutamate + archaeine15 in tRNA
show the reaction diagram
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ATP + L-glutamine = ?
show the reaction diagram
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Gln + H2O = Glu + NH3
show the reaction diagram
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L-glutamine + H2O = L-glutamate + NH3
show the reaction diagram
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benzyloxycarbonyl-Gly-methyl ester + Gln = benzyloxycarbonyl-Gly-Gln + ?
show the reaction diagram
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L-glutamine + H2O = L-glutamate + NH3
show the reaction diagram
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L-glutamine + H2O = L-glutamate + NH3
show the reaction diagram
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L-Gln + H2O = L-Glu + NH3
show the reaction diagram
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L-Gln + H2O = L-Glu + NH3
show the reaction diagram
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L-glutamine + H2O = L-glutamate + NH3
show the reaction diagram
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L-glutamine + H2O = L-glutamate + NH3
show the reaction diagram
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L-glutamine + H2O = L-glutamate + NH3
show the reaction diagram
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ATP + H2O + glutamine/out = ADP + phosphate + glutamine/in
show the reaction diagram
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L-glutamine = 5-amino-3,4-dihydro-2H-pyrrole-2-carboxylate + H2O
show the reaction diagram
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L-glutamine = D-glutamine
show the reaction diagram
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ATP + 4-methylene-L-glutamate + glutamine = AMP + diphosphate + glutamate + 4-methylene-L-glutamine
show the reaction diagram
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ATP + L-asparagine + L-glutamine = ADP + phosphate + L-asparaginyl-L-glutamine
show the reaction diagram
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ATP + L-Gln + HCO3- = ADP + phosphate + L-Glu + carbamoyl phosphate
show the reaction diagram
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ATP + ribose 5-phosphate + Gln = ADP + phosphate + 5-phosphoribosylamine + Glu
show the reaction diagram
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ATP + Ni-sirohydrochlorin + L-glutamine + H2O = ADP + phosphate + Ni-sirohydrochlorin a,c-diamide + L-glutamate
show the reaction diagram
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Product in Enzyme-catalyzed Reactions (95 results)

EC NUMBER
REACTION
REACTION DIAGRAM
LITERATURE
ENZYME 3D STRUCTURE
2-oxoglutarate + NH3 + NADH = L-Gln + NAD+ + H2O
show the reaction diagram
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2 L-glutamate + 2 oxidized ferredoxin = L-glutamine + 2-oxoglutarate + 2 reduced ferredoxin + 2 H+
show the reaction diagram
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5-L-glutamyl-L-alanine + 5-L-glutamyl-L-alanine = L-glutamine + 5-L-glutamyl-L-glutamyl-L-alanine
show the reaction diagram
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5-L-glutamyl-L-glutamine = 5-oxoproline + L-glutamine
show the reaction diagram
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L-glutaminyl 2-naphthylamide = L-glutamine + 2-naphthylamine
show the reaction diagram
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N-gamma-L-glutamylcyclohexylamine + NH4+ = cyclohexylamine + glutamine
show the reaction diagram
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5-phospho-beta-D-ribosylamine + diphosphate + L-glutamate = L-glutamine + 5-phospho-alpha-D-ribose 1-diphosphate + H2O
show the reaction diagram
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L-gamma-glutamyl-p-nitroanilide + H2O = L-glutamine + p-nitroaniline
show the reaction diagram
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L-Gln-7-amido-4-methylcoumarin + H2O = 7-amino-4-methylcoumarin + L-Gln
show the reaction diagram
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Gln-Leu + H2O = Gln + Leu
show the reaction diagram
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L-Gln-7-amido-4-methylcoumarin + H2O = 7-amino-4-methylcoumarin + L-Gln
show the reaction diagram
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Gln-7-amido-4-methylcoumarin + H2O = Gln + 7-amino-4-methylcoumarin
show the reaction diagram
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Ser-Met-Gln + H2O = Ser-Met + Gln
show the reaction diagram
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N-benzyloxycarbonyl-L-glutamine + H2O = benzyl carbonate + L-Gln
show the reaction diagram
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2-aminobenzoyl-Phe-Arg-Gln + H2O = 2-aminobenzoyl-Phe-Arg + Gln
show the reaction diagram
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beta-Asp-Gln + H2O = Asp + Gln
show the reaction diagram
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FVNQHLCGSHLVEALYLVCGERGFFYTPKA + H2O = FVN + Gln + HLCGSHL + VEALY + LVCGERGF + FYTPKA
show the reaction diagram
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insulin B chain + H2O = Phe-Val-Asn + Gln + HLCGSH + LVEA + Leu-Tyr + LVCGERGFFYTPKA
show the reaction diagram
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jasmonoyl-L-glutamine + H2O = jasmonic acid + L-glutamine
show the reaction diagram
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N-acetylglutamine + H2O = acetate + glutamine
show the reaction diagram
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Nalpha-acetyl-L-glutamine + H2O = L-glutamine + acetate
show the reaction diagram
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N-acetyl-L-glutamine + H2O = acetic acid + L-glutamine
show the reaction diagram
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beta-citryl-L-glutamine + H2O = citrate + L-glutamine
show the reaction diagram
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ATP + H2O + glutamine/out = ADP + phosphate + glutamine/in
show the reaction diagram
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D-Gln = L-Gln
show the reaction diagram
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Activator in Enzyme-catalyzed Reactions (31 results)

EC NUMBER
COMMENTARY
LITERATURE
ENZYME 3D STRUCTURE
increases enzyme production
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enhanced enzyme activity in jejunal mucosa
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enzyme induction when used as sole nitrogen source during growth
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prevents loss of activity
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activation
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activates
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enhanced enzyme activity in jejunal mucosa
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enhanced enzyme activity in jejunal mucosa of tumor-bearing rats
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activates 18% at 1 mM
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activates
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enhanced enzyme activity in jejunal mucosa
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Inhibitor in Enzyme-catalyzed Reactions (67 results)

EC NUMBER
COMMENTARY
LITERATURE
ENZYME 3D STRUCTURE
activity of NADH-GOGAT I significantly decreases in the presence of 10 mM glutamine
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1 mM, decrease of activity
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substrate inhibition
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competitive inhibition of agaritine hydrolysis
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with gamma-glutamylhydrazone of glyoxylate as substrate
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competitive inhibition of the histidine-pyruvate aminotransferase activity
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11% inhibition at 2 mM
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50 mM, 14% inhibition
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strong inhibition, 8 mM: 75% of activity compared to H2O
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competitive, 20 mM: 50% inhibition, 4-methylene-L-glutamine as substrate
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inhibition of enzyme activity in tumor tissue
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18% cell growth, 70% viability of cells
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competitive inhibition, 10 mM
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liver enzyme
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reaction of component I with NH4+ as substrate
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20 mM, 60% inhibition
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inhibition of enzyme activity in tumor tissue
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inhibition of hydroxylamine-dependent N4-OH CTP synthesis in presence of GTP
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Enzyme Kinetic Parameters

kcat Value (Turnover Number) (230 results)

EC NUMBER
TURNOVER NUMBER [1/S]
TURNOVER NUMBER MAXIMUM [1/S]
COMMENTARY
LITERATURE
1.15
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in 100 mM glycine-KCl-KOH buffer (pH 10.4)
430.4
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pH 8.5, 25°C
137
-
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0.78
-
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830
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pH 8.0, 25°C
7216
-
pH 7.6, 60°C
0.0025
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mutant C229R GlnRS, with tRNAGln
0.16
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pH 7.7, 30°C
0.16
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pH 7.7, wild-type enzyme

KM Value (541 results)

EC NUMBER
KM VALUE [MM]
KM VALUE MAXIMUM [MM]
COMMENTARY
LITERATURE
0.012
-
in 100 mM glycine-KCl-KOH buffer (pH 10.4)
2.7
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with pyruvate and NADPH as cosubstrates
6.1
-
-
280
-
-
353
-
acyl donor benzoyl-CoA
120
-
pH 8.0, 30°C
16
-
-
7
-
pH 8.6, 37°C, AAT I
15.92
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pH 7.6, 60°C
0.041
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wild-type LHT1, pH 5.8, temperature not specified in the publication
0.21
-
mutant C229R GlnRS, with tRNAGln
0.07
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pH 9.0, 37°C