Ligand L-alanine

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Basic Ligand Information

Molecular Structure
Picture of L-alanine (click for magnification)
Molecular Formula
BRENDA Name
InChIKey
C3H7NO2
L-alanine
QNAYBMKLOCPYGJ-REOHCLBHSA-N
Synonyms:
(S)-2-aminopropanoic acid, (S)-alanine, Ala, alanine, alpha-alanine, L-2-aminopropionic acid, L-Ala, L-alanin, L-alpha-alanine, L-alpha-aminopropionic acid

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

Roles as Enzyme Ligand

In Vivo Substrate in Enzyme-catalyzed Reactions (40 results)

EC NUMBER
PROVEN IN VIVO REACTION
REACTION DIAGRAM
LITERATURE
ENZYME 3D STRUCTURE
L-alanine + O2 = ? + H2O2
show the reaction diagram
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anthranilic acid + alanine + O2 = catechol + CO2 + NH3 + ?
show the reaction diagram
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L-alanine + pyruvate + NADH + H+ = 2,2'-iminodipropanoate + NAD+ + H2O
show the reaction diagram
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palmitoyl-CoA + L-alanine = CoA + (2S)-2-aminooctadecan-3-one + CO2
show the reaction diagram
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L-alanine + 4-(hydroxymethyl)-2-furancarboxaldehyde phosphate = pyruvate + 5-(aminomethyl)-3-furanmethanol phosphate
show the reaction diagram
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L-alanine + 2-oxoglutarate = pyruvate + L-glutamate
show the reaction diagram
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L-alanine + 4,5-dioxopentanoate = 5-aminolevulinate + pyruvate
show the reaction diagram
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L-alanine + glyoxylate = pyruvate + glycine
show the reaction diagram
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L-alanine + 3-hydroxypyruvate = pyruvate + L-serine
show the reaction diagram
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L-alanine + 1D-1-guanidino-1-deoxy-3-dehydro-scyllo-inositol = pyruvate + 1D-1-guanidino-3-amino-1,3-dideoxy-scyllo-inositol
show the reaction diagram
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L-alanine + 3-methyl-2-oxobutanoate = L-valine + pyruvate
show the reaction diagram
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L-alanine + pyridoxal 5'-phosphate = pyruvate + pyridoxamine 5'-phosphate
show the reaction diagram
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L-alanine + pyridoxal 5'-phosphate = pyruvate + pyridoxamine 5'-phosphate
show the reaction diagram
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L-alanine = D-alanine
show the reaction diagram
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ATP + L-alanine + tRNAPro = AMP + diphosphate + L-alanyl-tRNAPro
show the reaction diagram
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ATP + L-alanine + [acyl-carrier protein Atu2571] = AMP + diphosphate + L-alanyl-[acyl-carrier protein Atu2571]
show the reaction diagram
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ATP + Ala + Ala = ?
show the reaction diagram
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ATP + H2O + alanine/out = ADP + phosphate + alanine/in
show the reaction diagram
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In Vivo Product in Enzyme-catalyzed Reactions (57 results)

EC NUMBER
PROVEN IN VIVO REACTION
REACTION DIAGRAM
LITERATURE
ENZYME 3D STRUCTURE
(3S)-3-aminobutanoyl-CoA + pyruvate = acetoacetyl-CoA + L-alanine
show the reaction diagram
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L-glutamine + pyruvate = 2-oxoglutaramate + L-alanine
show the reaction diagram
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pyridoxamine + pyruvate = pyridoxal + L-alanine
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(2-aminoethyl)phosphonate + pyruvate = 2-phosphonoacetaldehyde + L-alanine
show the reaction diagram
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(R)-3-amino-2-methylpropanoate + pyruvate = 2-methyl-3-oxopropanoate + L-alanine
show the reaction diagram
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D-methionine + pyruvate = 4-methylthio-2-oxobutanoate + L-alanine
show the reaction diagram
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L-2,4-diaminobutanoate + pyruvate = L-2-amino-4-oxobutanoate + L-alanine
show the reaction diagram
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L-serine + pyruvate = 3-hydroxypyruvate + L-alanine
show the reaction diagram
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L-phenylalanine + pyruvate = phenylpyruvate + L-alanine
show the reaction diagram
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L-lysine + pyruvate = 2-aminoadipate 6-semialdehyde + L-alanine
show the reaction diagram
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L-arginine + pyruvate = 5-guanidino-2-oxopentanoate + L-alanine
show the reaction diagram
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4-aminobutanoate + pyruvate = succinate semialdehyde + L-alanine
show the reaction diagram
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L-tryptophan + pyruvate = indole-3-pyruvate + L-alanine
show the reaction diagram
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(2S,3S,5R,10S,12R,14R,15S,16S)-2-amino-12,16-dimethylicosane-3,5,10,14,15-pentol + pyruvate = (3S,5R,10S,12R,14R,15S,16S)-3,5,10,14,15-pentahydroxy-12,16-dimethylicosan-2-one + L-alanine
show the reaction diagram
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Ala-Leu + H2O = Ala + Leu
show the reaction diagram
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Ala-Leu + H2O = Ala + Leu
show the reaction diagram
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indole-3-acetic-acid-L-alanine + H2O = indole-3-acetic-acid + L-alanine
show the reaction diagram
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N-acetyl-L-alanine + H2O = acetate + L-alanine
show the reaction diagram
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N-acetylmuramoyl-L-alanine + H2O = N-acetylmuramate + L-alanine
show the reaction diagram
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N-carbamoyl-L-alanine + H2O = L-alanine + CO2 + NH3
show the reaction diagram
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L-aspartate = L-alanine + CO2
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2,2-dialkylglycine + pyruvate = dialkyl ketone + CO2 + L-alanine
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L-selenocysteine + reduced acceptor = selenide + L-alanine + acceptor
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D-alanine = L-alanine
show the reaction diagram
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ATP + H2O + alanine/out = ADP + phosphate + alanine/in
show the reaction diagram
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Substrate in Enzyme-catalyzed Reactions (235 results)

EC NUMBER
REACTION
REACTION DIAGRAM
LITERATURE
ENZYME 3D STRUCTURE
L-alanine + O2 = ? + H2O2
show the reaction diagram
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L-alanine + O2 = 2-oxo-propanoic acid + NH3
show the reaction diagram
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L-alanine + O2 = acetamide + CO2 + H2O
show the reaction diagram
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L-Ala + O2 = ? + CO2 + H2O
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L-alanine + L-ascorbate + O2 = ?
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alanine + H2O + NAD(P)+ = pyruvate + NH3 + NAD(P)H
show the reaction diagram
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L-alanine + H2O + NAD+ = ? + NH3 + NADH
show the reaction diagram
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L-alanine + H2O + NAD+ = pyruvate + NH3 + NADH
show the reaction diagram
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L-Ala + H2O + NAD+ = 2-oxopropanoate + NH3 + NADH
show the reaction diagram
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L-alanine + O2 + H2O = ?
show the reaction diagram
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L-Ala + H2O + oxidized 2,6-dichlorophenolindophenol = ?
show the reaction diagram
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Ala + pyruvate + NADH = ?
show the reaction diagram
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L-Ala + pyruvate + NADH = N-[1-(R)-(Carboxy)ethyl]-(S)-Ala + NAD+
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L-alanine + glycine = ?
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benzoyl-CoA + L-alanine = CoA + N-benzoyl-L-alanine
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acetyl-CoA + L-alanine = CoA + ?
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acetyl-CoA + L-alanine = CoA + N-acetyl-L-alanine
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benzoyl-CoA + alanine = CoA + N-benzoylalanine
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L-alanine + 2-oxoglutarate = pyruvate + L-glutamate
show the reaction diagram
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2-oxosuccinamic acid + L-alanine = L-asparagine + pyruvate
show the reaction diagram
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dTDP-4-dehydro-6-deoxy-D-glucose + L-alanine = dTDP-4-amino-4,6-dideoxy-D-galactose + pyruvate
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L-alanine + 2-oxoglutarate = pyruvate + L-glutamate
show the reaction diagram
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alpha-ketoglutarate + L-alanine = L-glutamate + pyruvate
show the reaction diagram
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L-alanine + 4,5-dioxopentanoate = 5-aminolevulinate + pyruvate
show the reaction diagram
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L-alanine + 3-phosphonooxypyruvate = O-phospho-L-serine + pyruvate
show the reaction diagram
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L-alanine + 1D-1-guanidino-1-deoxy-3-dehydro-scyllo-inositol = pyruvate + 1D-1-guanidino-3-amino-1,3-dideoxy-scyllo-inositol
show the reaction diagram
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L-alanine + alpha-ketomethiobutyrate = pyruvate + L-methionine
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phenylpyruvate + L-alanine = L-phenylalanine + pyruvate
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L-alanine + 3-methyl-2-oxobutanoate = L-valine + pyruvate
show the reaction diagram
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4-methyl-2-oxopentanoate + L-alanine = L-leucine + pyruvate
show the reaction diagram
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glyoxylate + L-alanine = ?
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L-alanine + glyoxylate = pyruvate + glycine
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L-alanine + pyridoxal 5'-phosphate = pyruvate + pyridoxamine 5'-phosphate
show the reaction diagram
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Ala = Ethylamine + CO2
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L-alanine = ?
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L-alanine = ?
show the reaction diagram
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L-alanine = ?
show the reaction diagram
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L-alanine + H2O = ?
show the reaction diagram
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L-Ala = D-Ala
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L-alanine = D-alanine
show the reaction diagram
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L-alanine = D-alanine
show the reaction diagram
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L-alanine = beta-alanine
show the reaction diagram
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ATP + L-alanine + tRNAPro = AMP + diphosphate + L-alanyl-tRNAPro
show the reaction diagram
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ATP + L-alanine + tRNAPhe = AMP + diphosphate + L-alanyl-tRNAPhe
show the reaction diagram
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ATP + L-alanine + tRNALys = AMP + L-alanyl-tRNALys + diphosphate
show the reaction diagram
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ATP + L-alanine + [acyl-carrier protein Atu2571] = AMP + diphosphate + L-alanyl-[acyl-carrier protein Atu2571]
show the reaction diagram
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ATP + Ala + Ala = ?
show the reaction diagram
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ATP + L-Arg + L-Ala = ADP + phosphate + L-Arg-L-Ala
show the reaction diagram
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ATP + L-asparagine + L-alanine = ADP + phosphate + L-asparaginyl-L-alanine + L-asparaginyl-L-asparagine
show the reaction diagram
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2 ATP + 2 L-Val + L-Ala = 2 ADP + 2 phosphate + L-Val-L-Val-L-Ala
show the reaction diagram
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ATP + L-alanine + UDP-MurNAc = ADP + phosphate + UDP-N-acetylmuramoyl-L-alanine
show the reaction diagram
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ATP + H2O + L-alanine/out = ADP + phosphate + L-alanine/in
show the reaction diagram
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ATP + H2O + alanine/out = ADP + phosphate + alanine/in
show the reaction diagram
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Product in Enzyme-catalyzed Reactions (692 results)

EC NUMBER
REACTION
REACTION DIAGRAM
LITERATURE
ENZYME 3D STRUCTURE
pyruvate + NADPH + NH3 = L-alanine + NADP+ + H2O
show the reaction diagram
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pyruvate + NH3 + NADPH + H+ = L-alanine + NADP+
show the reaction diagram
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N-methyl-L-alanine + acceptor + H2O = L-alanine + formaldehyde + reduced acceptor
show the reaction diagram
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N-methyl-L-alanine + acceptor + H2O = formaldehyde + L-alanine + reduced acceptor
show the reaction diagram
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N-methyl L-alanine + 2,6-dichlorophenolindophenol + H2O = L-alanine + formaldehyde + reduced 2,6-dichlorophenolindophenol
show the reaction diagram
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L-aspartate + pyruvate = oxaloacetate + L-alanine
show the reaction diagram
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(3S)-3-aminobutanoyl-CoA + pyruvate = acetoacetyl-CoA + L-alanine
show the reaction diagram
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L-ornithine + pyruvate = DELTA1-pyrroline-5-carboxylate + L-alanine
show the reaction diagram
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(S)-3-amino-2-methylpropanoate + pyruvate = D-methylmalonate semialdehyde + L-alanine
show the reaction diagram
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L-3,5,3'-triiodothyronine + pyruvate = 3-[4-(4-hydroxy-3-iodophenoxy)-3,5-diiodophenyl]-2-oxopropanoate + L-alanine
show the reaction diagram
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D-tryptophan + pyruvate = 3-indole-2-oxopropanoate + L-alanine
show the reaction diagram
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putrescine + pyruvate = 4-aminobutanal + L-alanine
show the reaction diagram
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L-lysine + pyruvate = 2-aminoadipate 6-semialdehyde + L-alanine
show the reaction diagram
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L-histidine + pyruvate = imidazol-5-yl-pyruvate + L-alanine
show the reaction diagram
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L-glutamate + pyruvate = 2-oxoglutarate + L-alanine
show the reaction diagram
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L-phenylalanine + pyruvate = phenylpyruvate + L-alanine
show the reaction diagram
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L-kynurenine + pyruvate = 4-(2-aminophenyl)-2,4-dioxobutanoate + L-alanine
show the reaction diagram
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6-acetamido-3-aminohexanoate + pyruvate = 6-acetamido-3-oxohexanoate + L-alanine
show the reaction diagram
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L-methionine + pyruvate = 4-methylsulfanyl-2-oxobutanoate + L-alanine
show the reaction diagram
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pyruvate + L-aspartate = L-alanine + oxaloacetate
show the reaction diagram
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pyruvate + L-glutamate = L-alanine + 2-oxoglutarate
show the reaction diagram
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pyruvate + putrescine = L-alanine + 4-aminobutanal
show the reaction diagram
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L-histidinol phosphate + pyruvate = 3-(imidazol-4-yl)-2-oxopropyl phosphate + L-Ala
show the reaction diagram
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4-aminobutanoate + pyruvate = succinate semialdehyde + L-alanine
show the reaction diagram
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L-tryptophan + pyruvate = indole-3-pyruvate + L-alanine
show the reaction diagram
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(2S,3S,5R,10S,12R,14R,15S,16S)-2-amino-12,16-dimethylicosane-3,5,10,14,15-pentol + pyruvate = (3S,5R,10S,12R,14R,15S,16S)-3,5,10,14,15-pentahydroxy-12,16-dimethylicosan-2-one + L-alanine
show the reaction diagram
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L-cysteine = L-alanine + sulfide
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Ala-tRNA + H2O = Ala + tRNA
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L-Ala benzyl ester + H2O = L-Ala + benzoic acid
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Ala-Trp + H2O = Ala + Trp
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Met-Ala + H2O = Met + Ala
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Asp-Ala + H2O = Asp + Ala
show the reaction diagram
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Ala-Leu + H2O = Ala + Leu
show the reaction diagram
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L-alanyl 4-nitroanilide + H2O = L-alanine + 4-nitroaniline
show the reaction diagram
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L-Ala-7-amido-4-methylcoumarin + H2O = L-Ala + 7-amino-4-methylcoumarin
show the reaction diagram
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L-alanyl 4-nitroanilide + H2O = L-alanine + 4-nitroaniline
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L-Asp-L-Ala + H2O = L-Asp + L-Ala
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Ser-His-Ala + H2O = Ser-His + Ala
show the reaction diagram
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Ala-Phe-Ala + H2O = Ala-Phe + Ala
show the reaction diagram
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N-benzyloxycarbonyl-Pro-Ala + H2O = N-benzyloxycarbonyl-Pro + Ala
show the reaction diagram
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Carbobenzoxy-Gly-Ala + H2O = Carbobenzoxy-Gly + Ala
show the reaction diagram
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N-benzyloxycarbonyl-Ala-Ala + H2O = N-benzyloxycarbonyl-Ala + L-alanine
show the reaction diagram
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N-carboxybenzoyl-Ala-Ala + H2O = N-carboxybenzoyl-Ala + L-alanine
show the reaction diagram
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N-succinyl-Ala-Phe-Ala + H2O = N-succinyl-Ala-Phe + alanine
show the reaction diagram
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GLQRA + H2O = GLQR + Ala
show the reaction diagram
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Carbobenzoxy-Gly-Ala + H2O = Carbobenzoxy-Gly + Ala
show the reaction diagram
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FVNQHLCGSHLVEALYLVCGERGFFYTPKA + H2O = L-Phe + VNQH + LCGSH + L-Leu + L-Val + L-Glu + L-Ala + L-Leu + L-Tyr + LVCG + ERG + L-Phe + L-Phe + YTPKA
show the reaction diagram
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Ala-Leu + H2O = Alanine + leucine
show the reaction diagram
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Abz-TTKLKAAK(Dnp)-NH2 + H2O = Abz-TTKL + L-Lys + L-Ala + AK(Dnp)-NH2
show the reaction diagram
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L-alanine amide + H2O = L-alanine + NH3
show the reaction diagram
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N-acetylalanine + H2O = acetate + alanine
show the reaction diagram
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Nalpha-acetyl-L-alanine + H2O = L-alanine + acetate
show the reaction diagram
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L-gamma-glutamyl-L-Ala + hydroxylamine = gamma-glutamyl hydroxamate + Ala
show the reaction diagram
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N-acetylmuramoyl-L-alanine + H2O = N-acetylmuramate + L-alanine
show the reaction diagram
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N-formyl-alanine + H2O = formate + alanine
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beta-cyanoalanine + H2O = alanine + NH3
show the reaction diagram
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L-alaninamide + H2O = L-alanine + NH3
show the reaction diagram
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N-carbamoyl-L-alanine + H2O = L-alanine + CO2 + NH3
show the reaction diagram
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N-feruloyl-L-alanine + H2O = ferulate + L-alanine
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N-Benzoyl-Ala + H2O = Benzoate + Ala
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ATP + aspartate = ADP + alanine + CO2
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gamma-glutamyl-L-alanine = 5-oxo-L-proline + L-alanine
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D-alanine = L-alanine
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D-Ala = L-Ala
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D-alanine = L-alanine
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D-Ala = L-Ala
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D-alanine = L-alanine
show the reaction diagram
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ATP + H2O + L-alanine/out = ADP + phosphate + L-alanine/in
show the reaction diagram
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ATP + H2O + alanine/out = ADP + phosphate + alanine/in
show the reaction diagram
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Activator in Enzyme-catalyzed Reactions (14 results)

EC NUMBER
COMMENTARY
LITERATURE
ENZYME 3D STRUCTURE
activation
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800% activation
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stimulates, stimulation pattern of MtrA is similar to that of MtrB
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13fold activation at 2.5 mM; 3fold activation at 2.5 mM
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activation
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activation of isoforms prolidase I and prolidase II
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infusion of alanine at 50% of resting energy expenditure for 36 h increases the enzyme activity more than twofold
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Inhibitor in Enzyme-catalyzed Reactions (115 results)

EC NUMBER
COMMENTARY
LITERATURE
ENZYME 3D STRUCTURE
slight inhibition
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weak inhibition at pH 8.5, strong inhibition at pH 10.0
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10% inhibition at 250 mM, with dimethylglycine
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slight inhibition
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noncompetitive against acetyl-CoA
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inhibition of serine utilization
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weak, asparagine/pyruvate reaction
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competitive
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with beta-alanine + glyoxylate as substrate, not (R)-isomer
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competitive vs. L-serine
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noncompetitive inhibition with respect to delta-aminovalerate, competitive inhibition to 2-oxoglutarate
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feed-back inhibition, no growth of the organism in presence of L-alanine
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35% inhibition at 10 mM
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no significant effect on AK activity at 5 and 20 mM
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27-34% inhibition of the reaction
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93% residual activity at 1 mM
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isoenzyme II, french bean
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poor competitive inhibitor of Ala-Gly hydrolysis
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weak
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5.0 mM
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competitive
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weak
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weak
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inhibits glutamine hydrolysis and Gln-dependent carbamoyl phosphate synthesis
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Enzyme Kinetic Parameters

kcat Value (Turnover Number) (141 results)

EC NUMBER
TURNOVER NUMBER [1/S]
TURNOVER NUMBER MAXIMUM [1/S]
COMMENTARY
LITERATURE
0.000317
-
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1084.6
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pH and temperature not specified in the publication
51.7
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apparent value, isozyme St/AlDH1, with 0.3 mM NADH and 5 mM pyruvate, in 0.1 M PIPES-NaOH (pH 7.2), at 30C
15.4
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with 4-oxobutanoate as cosubstrate, in 50 mM TABS (pH 9), 1.5 mM dithiothreitol, 0.625 mM EDTA, 0.1 mM pyridoxal 5'-phosphate, 10% (v/v) glycerol, at 30C
41
-
; 30C, pH 9.0
9.3
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pH 8.5, 25C, synthesis of (2-aminoethyl)phosphonate
131
-
-