Ligand L-serine

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Basic Ligand Information

Molecular Structure
Picture of L-serine (click for magnification)
Molecular Formula
BRENDA Name
InChIKey
C3H7NO3
L-serine
MTCFGRXMJLQNBG-REOHCLBHSA-N
Synonyms:
L-Ser, S-serine, Ser, serine
Pathway Source
Pathways
MetaCyc
achromobactin biosynthesis, archaetidylserine and archaetidylethanolamine biosynthesis, ceramide de novo biosynthesis, choline biosynthesis I, D-cycloserine biosynthesis more


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

Roles as Enzyme Ligand

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

EC NUMBER
PROVEN IN VIVO REACTION
REACTION DIAGRAM
LITERATURE
ENZYME 3D STRUCTURE
L-serine + NADP+ = 2-aminomalonate semialdehyde + NADPH
show the reaction diagram
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L-serine + NAD+ = ?
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L-serine + H2O + NAD+ = 3-hydroxypyruvate + NH3 + NADH + NH3 + NADH + H+
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L-Ser + H2O + O2 = 2-oxo-3-hydroxypropionic acid + NH3 + H2O2
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L-serine + glyoxylate = 3-hydroxypyruvate + glycine
show the reaction diagram
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L-serine + pyruvate = 3-hydroxypyruvate + L-alanine
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ATP + L-serine = ADP + O-phospho-L-serine
show the reaction diagram
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ADP + L-serine = AMP + O-phospho-L-serine
show the reaction diagram
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diphosphate + L-serine = phosphate + O-phospho-L-serine
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CDP-ethanolamine + L-serine = CMP + L-serine-ethanolamine phosphate
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L-serine + indole = L-tryptophan + H2O
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L-Serine + pyrazole = ?
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L-serine = pyruvate + NH3
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L-serine = D-serine
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ATP + gamma-L-glutamyl-L-cysteine + L-serine = ADP + phosphate + gamma-L-glutamyl-L-cysteinyl-L-serine
show the reaction diagram
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ATP + H2O + serine/out = ADP + phosphate + serine/in
show the reaction diagram
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In Vivo Product in Enzyme-catalyzed Reactions (14 results)

EC NUMBER
PROVEN IN VIVO REACTION
REACTION DIAGRAM
LITERATURE
ENZYME 3D STRUCTURE
L-alanine + 3-hydroxypyruvate = pyruvate + L-serine
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L-cysteine + 'activated' tRNA = L-serine + tRNA containing a thionucleotide
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phospho-L-serine + H2O = L-serine + phosphate
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phosphatidylserine + H2O = serine + phosphatidic acid
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glycerophosphoserine + H2O = sn-glycerol 3-phosphate + serine
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Ser-Leu + H2O = Ser + Leu
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Ser-Leu + H2O = Ser + Leu
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ATP + H2O + serine/out = ADP + phosphate + serine/in
show the reaction diagram
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Substrate in Enzyme-catalyzed Reactions (289 results)

EC NUMBER
REACTION
REACTION DIAGRAM
LITERATURE
ENZYME 3D STRUCTURE
L-serine + NADP+ = 2-aminomalonate semialdehyde + NADPH
show the reaction diagram
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L-serine + NADP+ = ?
show the reaction diagram
-
L-serine + NAD+ = ?
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L-serine + NAD+ = 3-oxo-L-alanine + NADH + H+
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L-serine + H2O + NAD+ = 3-hydroxy-2-oxopropanoate + NH3 + NADH
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L-serine + H2O + NAD+ = 3-hydroxy-2-oxopropanoate + NH3 + NADH
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L-serine + pyruvate + NADPH = N2-(D-1-carboxyethyl)-L-Ser + NADP+ + H2O
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L-Ser + pyruvate + NADH = ?
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L-Ser + pyruvate + NADH = N-[1-(R)-(Carboxy)ethyl]-(S)-Ser + NAD+
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L-serine + 2,6-dichlorophenolindophenol + H2O = ? + reduced 2,6-dichlorophenolindophenol
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succinyl-CoA + L-serine = ?
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6-carboxyhexanoyl-CoA + L-serine = 9-hydroxy-8-amino-7-oxononanoate + CoA
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benzoyl-CoA + serine = CoA + N-benzoylserine
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L-serine + 2-oxoglutarate = 3-hydroxy-2-oxopropionic acid + L-glutamate
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2-oxosuccinamic acid + L-serine = L-asparagine + 3-hydroxy-2-oxopropanoate
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serine + 2-oxoglutarate = 3-hydroxy-2-oxopropanoate + glutamate
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glyoxylate + L-serine = hydroxypyruvate + glycine
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L-serine + glyoxylate = 3-hydroxy-2-oxopropanoate + glycine
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L-serine + 2-oxoglutarate = 3-hydroxy-2-oxopropanoate + L-glutamate
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L-serine + 4,5-dioxopentanoate = 5-aminolevulinate + 3-hydroxy-2-oxopropanoate
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L-serine + phenylpyruvate = 3-hydroxy-2-oxopropanoate + L-phenylalanine
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L-serine + glyoxylate = 3-hydroxy-2-oxopropanoate + glycine
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L-serine + pyruvate = 3-hydroxy-2-oxopropanoate + L-alanine
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pyruvate + L-serine = L-alanine + 3-hydroxy-2-oxopropanoate
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ATP + L-serine = ADP + O-phospho-L-serine
show the reaction diagram
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ADP + L-serine = AMP + O-phospho-L-serine
show the reaction diagram
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diphosphate + L-serine = phosphate + O-phospho-L-serine
show the reaction diagram
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4-nitrophenyl-N-acetyl-beta-D-galactosaminide + L-Ser = ?
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L-serine + H2O = ?
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L-Ser = ?
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L-serine = glycine + formaldehyde
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L-serine = pyruvate + NH3
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L-serine = ?
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L-serine = pyruvate + NH3
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L-serine = ?
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L-serine = pyruvate + NH3
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L-serine + H2O = NH3 + ?
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L-serine + H2O = hydrogen sulfide + pyruvate + NH3
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L-serine = D-serine
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ATP + L-serine + tRNALys = AMP + L-seryl-tRNALys + diphosphate
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ATP + L-serine + tRNAAla = AMP + diphosphate + L-seryl-tRNAAla
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ATP + UDP-N-acetyl-alpha-D-muramoyl-L-alanyl-D-glutamate + L-serine = ADP + phosphate + UDP-N-acetyl-alpha-D-muramoyl-L-alanyl-L-serine
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ATP + gamma-L-glutamyl-L-cysteine + L-serine = ADP + phosphate + gamma-L-glutamyl-L-cysteinyl-L-serine
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ATP + gamma-Glu-L-Cys + Ser = ADP + phosphate + gamma-Glu-Cys-Ser
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ATP + L-Arg + L-Ser = ADP + phosphate + L-Arg-L-Ser
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2 ATP + 2 L-Val + L-Ser = 2 ADP + 2 phosphate + L-Val-L-Val-L-Ser
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ATP + H2O + serine/out = ADP + phosphate + serine/in
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Product in Enzyme-catalyzed Reactions (155 results)

EC NUMBER
REACTION
REACTION DIAGRAM
LITERATURE
ENZYME 3D STRUCTURE
5'-phospho-pyridoxyl-L-serine + H2O + O2 = pyridoxal 5'-phosphate + L-serine + H2O2
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N-methyl L-serine + 2,6-dichlorophenolindophenol + H2O = L-serine + formaldehyde + reduced 2,6-dichlorophenolindophenol
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L-cysteine + H2O = L-serine + H2S
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L-glutamine + 3-hydroxypyruvate = 2-oxoglutaramate + L-serine
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L-alanine + hydroxypyruvate = pyruvate + L-serine
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L-phenylalanine + hydroxypyruvate = phenylpyruvate + L-serine
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L-kynurenine + hydroxypyruvate = 4-(2-aminophenyl)-2,4-dioxobutanoate + L-serine
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L-glutamine + 3-hydroxypyruvate = 2-oxoglutaramate + L-serine
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O-acetylserine + H2O = serine + acetate
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L-phosphoserine + H2O = L-serine + phosphate
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phospho-L-serine + H2O = L-serine + phosphate
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O-phospho-L-serine + H2O = Ser + phosphate
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phospho-L-serine + H2O = L-serine + phosphate
show the reaction diagram
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O-phospho-L-serine + H2O = L-serine + phosphate
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L-serine-phosphoethanolamine + H2O = L-serine + ethanolamine phosphate
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1-alkyl-sn-glycero-3-phospho-L-serine + H2O = 1-alkyl-sn-glycerol 3-phosphate + L-serine
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serine-O-sulfate + H2O = serine + SO42-
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L-serine-7-amido-4-methylcoumarin + H2O = L-serine + 7-amino-4-methylcoumarin
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L-Ser-7-amido-4-methylcoumarin + H2O = L-Ser + 7-amino-4-methylcoumarin
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Ser-Gly-Gly + H2O = Ser + Gly-Gly
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Ser-7-amido-4-methylcoumarin + H2O = Ser + 7-amino-4-methylcoumarin
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Ser-amide + H2O = Ser + NH3
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Met-Ser + H2O = Met + Ser
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L-Ser-2-naphthylamide + H2O = L-Ser + 2-naphthylamine
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Ser-Leu + H2O = Ser + Leu
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L-Ser-7-amido-4-methylcoumarin + H2O = L-Ser + 7-amino-4-methylcoumarin
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Ser-Ala + H2O = Ser + Ala
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L-Ser-7-amido-4-methylcoumarin + H2O = L-Ser + 7-amino-4-methylcoumarin
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Ser-7-amido-4-methylcoumarin + H2O = Ser + 7-amino-4-methylcoumarin
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L-Ser-Gly + H2O = L-Ser + Gly
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Ser-His + H2O = Ser + His
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L-Asp-L-Ser + H2O = L-Asp + L-Ser
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Ser-Tyr-NH2 + H2O = Ser + Tyr + NH3
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L-Ala-L-Pro-L-Ser + H2O = L-Ala-L-Pro + L-Ser
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Met-Ala-Ser + H2O = Met-Ala + Ser
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L-Leu-L-Leu-L-Val-L-Tyr-L-Ser + H2O = Leu-Leu + Val-Tyr + Ser
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N-benzyloxycarbonyl-Pro-Ser + H2O = N-benzyloxycarbonyl-Pro + Ser
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Leu-Asp-Ser + H2O = Leu-Asp + Ser
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Ser-Ala + H2O = Ser + Ala
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Ac-Asp-Arg-Val-Tyr-Ile-His-Pro-Phe-His-Leu-Leu-Val-Tyr-Ser + H2O = Ac-Asp-Arg-Val-Tyr-Ile-His-Pro-Phe-His-Leu-Leu-Val-Tyr + L-serine
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Ac-Asp-Arg-Val-Tyr-Ile-His-Pro-Phe-His-Leu-Leu-Val-Tyr-Ser + H2O = Ac-Asp-Arg-Val-Tyr-Ile-His-Pro-Phe-His-Leu-Leu-Val-Tyr + L-serine
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2-aminobenzoyl-Phe-Arg-Ser + H2O = 2-aminobenzoyl-Phe-Arg + Ser
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N-acetyl-Ala-Ser + H2O = N-acetyl-Ala + Ser
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pyroglutamyl-Ser + H2O = pyroglutamate + Ser
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beta-Asp-Ser + H2O = Asp + Ser
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N-benzyloxycarbonyl-Gly-Pro-Ser + H2O = N-benzyloxycarbonyl-Gly-Pro + L-Ser
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L-Ser-beta-naphthylamide + H2O = L-Ser + beta-naphthylamine
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Thr-Ser + H2O = Thr + Ser
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L-Ser-7-amido-4-methylcoumarin + H2O = L-Ser + 7-amino-4-methylcoumarin
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L-serine amide + H2O = L-serine + NH3
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L-serinamide + H2O = L-serine + NH3
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N-carbamoyl-L-serine + H2O = L-serine + CO2 + NH3
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(S)-2-amino-3-(3-hydroxy-4-oxo-4H-pyridin-1-yl)propanoate + H2O = 3-hydroxy-4(1H)-pyrid-4-one + L-serine
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Nalpha-benzyloxycarbonyl-L-Ser + H2O = benzyl alcohol + CO2 + L-Ser
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L-2-oxooxazolidine-4-carboxylate + H2O + ATP = L-serine + ADP + phosphate
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L-tryptophan + D-glyceraldehyde 3-phosphate + H2O = indole-3-glycerol phosphate + L-serine
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D-serine = L-serine
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(gamma-L-glutamyl)-L-serine = 5-oxoproline + L-serine
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D-serine = L-serine
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ATP + H2O + serine/out = ADP + phosphate + serine/in
show the reaction diagram
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Activator in Enzyme-catalyzed Reactions (17 results)

EC NUMBER
COMMENTARY
LITERATURE
ENZYME 3D STRUCTURE
activates
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1 mM concentration, 12% activation free protein, 10% activation immobilized protein
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stabilizes the dimeric form of the enzyme
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13fold activation at 2.5 mM; 3fold activation at 2.5 mM
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human serine dependent PLA2
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prolinase activity in erythrocytes from both the normal control and the patients with prolidase (EC 3.4.13.9) deficiency is activated
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activation of isoforms prolidase I and prolidase II
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activates
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1 mM, relative activity 140%
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acticates liver enzyme, competitively inhibits kidney and brain enzyme
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activates
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121% activity at 5 mM with L-methionine as substrate, 114% activity at 50 mM with D-methionine as substrate
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Inhibitor in Enzyme-catalyzed Reactions (101 results)

EC NUMBER
COMMENTARY
LITERATURE
ENZYME 3D STRUCTURE
noncompetitive inhibition
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non-competitive
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pH 7.6, 30°C
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competitive inhibitor
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weak, competitive
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weak
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about 15% inhibition at 100 mM
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competitive to O-acetylserine
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asparagine/pyruvate reaction
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10 mM, 22% inhibition
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competitive versus L-aspartate
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weak, 20% inhibition at 15 mM
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competitive vs. asparagine
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competitive inhibitor of histidine transamination
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selective ChE inhibitor, 93.1-99.2% inhibition at 0.0005 mM
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isoenzyme I, french bean
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partial inhibition, 8 mM: 95% of activity compared to H2O
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competitive inhibition, 10 mM
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activates liver enzyme, competitively inhibits kidney and brain enzyme
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competitive
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86% inhibition at 4 mM
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20% cell growth, 25% viability of cells
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Enzyme Kinetic Parameters

kcat Value (Turnover Number) (307 results)

EC NUMBER
TURNOVER NUMBER [1/S]
TURNOVER NUMBER MAXIMUM [1/S]
COMMENTARY
LITERATURE
9.41
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at pH 9.5 and 22°C
0.24
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wild-type, pH 10.2, temperature not specified in the publication
10.4
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pH 11.0, 37°C, recombinant His-tagged wild-type enzyme
23.64
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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 30°C
1.2
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pH 8.0, 25°C
218
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pH 7.5, 85°C
0.0303
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pH 7.8, 37°C, mutant enzyme Y72F
0.18
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at pH 8.5 and 50°C
13.3
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pH 8.2, 37°C
3.8
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pH 8.0, 37°C, presence of 1 mM ATP, racemization reaction
12.7
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L-Ser-dependent ATP-diphosphate exchange

KM Value (493 results)

EC NUMBER
KM VALUE [MM]
KM VALUE MAXIMUM [MM]
COMMENTARY
LITERATURE
46.7
-
at pH 9.5 and 22°C
2.5
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pH 11.0, 37°C, recombinant His-tagged wild-type enzyme
3.6
-
pyruvate and NADH as cosubstrates
0.7
-
-
16
-
cosubstrate pyruvate, 37°C
37
-
pH 8.0, 25°C
5.1
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pH 7.5, 85°C
1.9
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pH 7.8, 37°C
0.12
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pH 7.5, 37°C
1
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pH 7.0, 37°C
0.085
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pH 7.2, 37°C, membrane-bound enzyme