Ligand L-asparagine

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Basic Ligand Information

Molecular Structure
Picture of L-asparagine (click for magnification)
Molecular Formula
BRENDA Name
InChIKey
C4H8N2O3
L-asparagine
DCXYFEDJOCDNAF-REOHCLBHSA-N
Synonyms:
Asn, asparagine, L-Asn, L-asparagin


Show all pahtways known for Show all BRENDA pathways known for L-asparagine

Roles as Enzyme Ligand

In Vivo Substrate in Enzyme-catalyzed Reactions (12 results)

EC NUMBER
PROVEN IN VIVO REACTION
REACTION DIAGRAM
LITERATURE
ENZYME 3D STRUCTURE
L-asparagine + 2-oxoglutarate + O2 = (2S,3S)-3-hydroxyasparagine + succinate + CO2
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L-asparagine + H2O + O2 = 4-amino-2,4-dioxobutanoate + NH3 + H2O2
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L-Asn + H2O + O2 = 2-oxosuccinamic acid + NH3 + H2O2
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L-asparagine + H2O = L-aspartate + NH3
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L-asparagine + H2O = L-aspartate + NH3
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L-asparagine + H2O = L-aspartate + NH3
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L-asparagine = D-asparagine
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ATP + L-asparagine + tRNAAsn = AMP + diphosphate + L-asparaginyl-tRNAAsn
show the reaction diagram
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In Vivo Product in Enzyme-catalyzed Reactions (10 results)

EC NUMBER
PROVEN IN VIVO REACTION
REACTION DIAGRAM
LITERATURE
ENZYME 3D STRUCTURE
Asn-Leu + H2O = Asn + Leu
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Asn-Leu + H2O = Asn + Leu
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beta-Cyano-L-alanine + H2O = L-Asparagine
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ATP + L-aspartate + NH3 = AMP + diphosphate + L-asparagine
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ATP + L-aspartate + NH3 = ADP + phosphate + L-asparagine
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Substrate in Enzyme-catalyzed Reactions (99 results)

EC NUMBER
REACTION
REACTION DIAGRAM
LITERATURE
ENZYME 3D STRUCTURE
L-asparagine + 2-oxoglutarate + O2 = (2S,3S)-3-hydroxyasparagine + succinate + CO2
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L-asparagine + H2O + O2 = ?
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carbamoyl phosphate + L-asparagine = phosphate + N-carbamoyl-L-asparagine
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phenylacetyl-CoA + L-asparagine = ? + CoA
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benzoyl-CoA + L-asparagine = CoA + N-benzoylasparagine
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L-asparagine + 2-oxoglutarate = 4-amino-2,4-dioxobutanoate + L-glutamate
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L-asparagine + glyoxylate = 4-amino-2,4-dioxobutanoate + glycine
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L-asparagine + 2-oxoglutarate = 2,4-dioxo-4-aminobutanoate + L-glutamate
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L-asparagine + 4,5-dioxopentanoate = 5-aminolevulinate + 4-amino-2,4-dioxobutanoic acid
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L-asparagine + glyoxylate = 4-amino-2,4-dioxobutanoate + glycine
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L-asparagine + 2-oxoglutarate = 2-oxosuccinamate + L-glutamate
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asparagine + glyoxylate = 2-oxosuccinamate + glycine
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L-asparagine + phenylpyruvate = 2-oxosuccinamate + L-phenylalanine
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chorismate + L-asparagine = 4-amino-4-deoxychorismate + L-aspartate
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4-methyl-2-oxopentanoate + L-asparagine = L-leucine + 2-oxosuccinamic acid
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ATP + L-asparagine = ?
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Asn + H2O = Asp + NH3
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L-asparagine + H2O = L-aspartate + NH3
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asparagine + H2O = aspartic acid + NH3
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L-asparagine + H2O = L-aspartate + NH3
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L-asparagine + H2O = L-aspartate + NH3
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L-asparagine + H2O = L-aspartate + NH3
show the reaction diagram
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L-asparagine + H2O = L-aspartate + NH3
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L-asparagine + H2O = ?
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L-asparagine = ?
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L-asparagine + H2O = ?
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L-asparagine = D-asparagine
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ATP + L-asparagine + tRNAAsp = AMP + diphosphate + L-asparaginyl-tRNAAsp
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2 ATP + 2 L-Val + L-Asn = 2 ADP + 2 phosphate + L-Val-L-Val-L-Asn
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ATP + ribose 5-phosphate + Asn = ADP + phosphate + 5-phosphoribosylamine + Asp
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ATP + deamido-NAD+ + Asn = AMP + diphosphate + NAD+ + Asp
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ATP + H2O + L-asparagine/out = ADP + phosphate + L-asparagine
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Product in Enzyme-catalyzed Reactions (69 results)

EC NUMBER
REACTION
REACTION DIAGRAM
LITERATURE
ENZYME 3D STRUCTURE
L-leucine + oxaloacetate = 2-oxoisohexanoate + L-asparagine
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L-serine + 2-oxosuccinamate = 3-hydroxypyruvate + L-asparagine
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GlcNAcAsn + H2O = N-acetyl-D-glucosamine + L-asparagine
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1-beta-aspartyl-2-acetamido-1,2-dideoxy-D-glucosylamine + H2O = N-acetylglucosamine + asparagine
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Asn-Leu + H2O = Asn + Leu
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L-Asn-7-amido-4-methylcoumarin + H2O = L-Asn + 7-amino-4-methylcoumarin
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L-Asn-L-Pro-L-Thr-L-Asn-L-Leu-L-His + H2O = L-Asn + L-Pro-L-Thr-L-Asn-L-Leu-L-His
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Asn-7-amido-4-methylcoumarin + H2O = Asn + 7-amino-4-methylcoumarin
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L-Asn-D-Glu + H2O = L-Asn + D-Glu
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2-aminobenzoyl-Phe-Arg-Asn + H2O = 2-aminobenzoyl-Phe-Arg + Asn
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acetyl-Met-Asn + H2O = acetyl-Met + Asn
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phenylacetyl-L-asparagine + H2O = L-asparagine + phenylacetic acid
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Nalpha-acetyl-L-asparagine + H2O = L-asparagine + acetate
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Nalpha-benzyloxycarbonyl-L-Asn + H2O = benzyl alcohol + CO2 + L-Asn
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N-carbamoyl-L-asparagine + H2O = L-asparagine + CO2 + NH3
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3-cyano-L-alanine + H2O = L-aspartate + asparagine
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beta-cyano-L-alanine + H2O = asparagine + aspartic acid
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beta-Cyano-L-alanine + H2O = L-Asparagine
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ATP + H2O + L-asparagine/out = ADP + phosphate + L-asparagine
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Activator in Enzyme-catalyzed Reactions (15 results)

EC NUMBER
COMMENTARY
LITERATURE
ENZYME 3D STRUCTURE
enzyme induction when used as sole nitrogen source during growth
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stimulation, 112% of non-stimulated activity
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required
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slight activation
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Inhibitor in Enzyme-catalyzed Reactions (39 results)

EC NUMBER
COMMENTARY
LITERATURE
ENZYME 3D STRUCTURE
76% inhibition at 10 mM asparagine in the growth medium
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weak
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competitive vs. serine
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competitive inhibition, Ki: 0.454 mM
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competitive inhibition of glutaminase activity, Ki: 0.02 mM
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strong inhibition, 8 mM: 76% of activity compared to H2O
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very slight inhibition, 20 mM: 3% inhibition
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inhibition via chelating Mn2+, allantoate protects and reverses, competitive or mixed-type inhibition
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competitive inhibition, 10 mM
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inhibits 4% at 1 mM
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weak
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less effective inhibitor, Ki-value above 150 mM
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35% cell growth, 70% viability of cells
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Enzyme Kinetic Parameters

kcat Value (Turnover Number) (60 results)

EC NUMBER
TURNOVER NUMBER [1/S]
TURNOVER NUMBER MAXIMUM [1/S]
COMMENTARY
LITERATURE
4.98
-
pH 7.5, 25°C
0.13
-
pH 8.0, 25°C
1606
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at pH 9.0 and 50°C
5.8
-
-
0.027
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37°C, pH 7.2, amidotransferase activity
0.027
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37°C, pH 7.2, amidotransferase activity

KM Value (174 results)

EC NUMBER
KM VALUE [MM]
KM VALUE MAXIMUM [MM]
COMMENTARY
LITERATURE
0.479
-
pH 7.5, 25°C
18.1
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apparent value, at pH 8.0 and 37°C
122
-
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129
-
acyl donor benzoyl-CoA
7.14
-
-
1
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cosubstrate phenylpyruvate
1
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pH 8.0, 25°C
16
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pH 8.0, 25°C, aspartokinase III
0.0224
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37°C, pH 7.2, amidotransferase activity

Ki Value (9 results)

EC NUMBER
KI VALUE [MM]
KI VALUE MAXIMUM [MM]
COMMENTARY
LITERATURE
14
-
-
110
-
-
3
-
pH 8.1, 30°C
0.454
-
competitive inhibition
0.02
-
competitive inhibition of glutaminase activity
1.13
-
pH 8.0, 37°C

IC50 Value (8 results)

EC NUMBER
IC50 VALUE
IC50 VALUE MAXIMUM
COMMENTARY
LITERATURE

References & Links

Links to other databases for L-asparagine

ChEBI
PubChem
ChEBI
PubChem