Ligand L-lysine

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Basic Ligand Information

Molecular Structure
Picture of L-lysine (click for magnification)
Molecular Formula
BRENDA Name
InChIKey
C6H14N2O2
L-lysine
KDXKERNSBIXSRK-YFKPBYRVSA-N
Synonyms:
(S)-Lys, (S)-lysine, 6,6-dideutrolysine, alpha-lysine, homoornithine, L-2,6-diaminohexanoate, L-Lys, L-Lysine derivatives, L-lysine[side 2], Lys, lysine
Pathway Source
Pathways


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

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-lysine + O2 = ? + H2O2
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L-lysine + NADPH + H+ + O2 = L-lysine N6-oxide + NADP+ + H2O
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L-lysine + O2 + H2O = 6-amino-2-oxohexanoate + NH3 + H2O2
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L-arginine + L-lysine = L-ornithine + L-homoarginine
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D-glyceraldehyde 3-phosphate + L-lysine = N2-(2-carboxyethyl)-L-lysine + phosphate
show the reaction diagram
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L-lysine + 8-amino-7-oxononanoate = (S)-2-amino-6-oxohexanoate + 7,8-diaminononanoate
show the reaction diagram
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L-lysine + 2-oxoglutarate = 2-aminoadipate 6-semialdehyde + L-glutamate
show the reaction diagram
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L-lysine + pyruvate = 2-aminoadipate 6-semialdehyde + L-alanine
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L-lysine = 1,5-diaminopentane + CO2
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L-lysine = cadaverine + CO2
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L-lysine = D-lysine
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L-lysine = D-lysine
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L-lysine = 2,5-diaminohexanoate
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ATP + indoleacetate + L-Lys = ?
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alpha-aminoadipic acid + L-valine + L-lysine + ? = L-delta-alpha-aminoadipyl-L-cysteinyl-D-valine + ?
show the reaction diagram
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ATP + H2O + lysine/out = ADP + phosphate + lysine/in
show the reaction diagram
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In Vivo Product in Enzyme-catalyzed Reactions (17 results)

EC NUMBER
PROVEN IN VIVO REACTION
REACTION DIAGRAM
LITERATURE
ENZYME 3D STRUCTURE
N2-(D-1-carboxyethyl)-L-lysine + NADP+ + H2O = L-lysine + pyruvate + NADPH
show the reaction diagram
-
-
N6-(L-1,3-dicarboxypropyl)-L-lysine + NAD+ + H2O = L-lysine + 2-oxoglutarate + NADH + H+
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-
Met-Lys-bradykinin + H2O = Met + Lys + bradykinin
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-
biocytin + H2O = biotin + L-lysine
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-
[carrier protein LysW]-C-terminal-gamma-(L-lysyl)-L-glutamate + H2O = [carrier protein LysW]-C-terminal-L-glutamate + L-lysine
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-
epsilon-(gamma-L-glutamyl)-L-lysine = L-lysine + 5-oxo-L-proline
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-
ATP + H2O + lysine/out = ADP + phosphate + lysine/in
show the reaction diagram
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-

Substrate in Enzyme-catalyzed Reactions (190 results)

EC NUMBER
REACTION
REACTION DIAGRAM
LITERATURE
ENZYME 3D STRUCTURE
L-lysine + O2 = ? + H2O2
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L-Lysine + H2O + NAD+ = ? + NH3 + NADH
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L-lysine + H2O + NAD+ = 6-amino-2-oxohexanoate + NH3 + NADH + H+
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lysine + H2O + O2 = 2-aminohexanoic acid + NH3 + H2O2
show the reaction diagram
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L-lysine + H2O + O2 = 2-oxolysine + NH3 + H2O2
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2 lysine + homocystine = glutathione disulfide + 2 homocysteine
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S-adenosyl-L-methionine + L-Lys = S-adenosyl-L-homocysteine + methyl-L-Lys
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S-adenosyl-L-methionine + L-Lys = S-adenosyl-L-homocysteine + N6-methyl-L-lysine
show the reaction diagram
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carbamoyl phosphate + L-lysine = phosphate + L-homocitrulline
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arginine + lysine = homoarginine + ornithine
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L-arginine + L-lysine = L-ornithine + L-homoarginine
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benzoyl-CoA + lysine = ?
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S-ubiquitinyl-[E1 ubiquitin-activating enzyme]-L-cysteine + L-lysine = [E1 ubiquitin-activating enzyme]-L-cysteine + N6-monoubiquitinyl-L-lysine
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thiamine + L-lysine = ?
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D-glyceraldehyde 3-phosphate + L-lysine = N2-(2-carboxyethyl)-L-lysine + phosphate
show the reaction diagram
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L-Lys + 2-oxo-4-phenyl-butanoic acid = L-homophenylalanine + 2-keto-6-aminocaproate
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L-lysine + 8-amino-7-oxononanoate = (S)-2-amino-6-oxohexanoate + 7,8-diaminononanoate
show the reaction diagram
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L-lysine + 2-oxoglutarate = glutamate + 2-amino-7-oxooctanoic acid
show the reaction diagram
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pyruvate + L-lysine = L-alanine + ?
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L-lysine + 2-oxoglutarate = L-glutamate + (S)-2-amino-6-oxohexanoate
show the reaction diagram
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L-lysine + 2-oxoglutarate = 2-oxo-6-aminohexanoate + L-glutamate
show the reaction diagram
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L-lysine + 4,5-dioxopentanoate = 5-aminolevulinate + 6-amino-2-oxohexanoate
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lysine + pyruvate = 6-amino-2-oxohexanoate + alanine
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L-lysine + alpha-ketomethiobutyrate = 2-oxo-6-amino-hexanoate + L-methionine
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L-lysine + glyoxylate = ?
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L-lysine + pyruvate = 2-aminoadipate 6-semialdehyde + L-alanine
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L-lysine + oxaloacetic acid = ?
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L-lysine + H2O = ? + NH3
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L-lysine = ?
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L-lysine = 1,5-diaminopentane + CO2
show the reaction diagram
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L-lysine = ?
show the reaction diagram
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L-lysine = cadaverine + CO2
show the reaction diagram
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L-lysine = L-pipecolate + NH3
show the reaction diagram
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L-lysine + H2O = ?
show the reaction diagram
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L-lysine = D-lysine
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L-lysine = D-lysine
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L-lysine = (3R)-3-methyl-D-ornithine
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alpha-aminoadipic acid + L-valine + L-lysine + ? = L-delta-alpha-aminoadipyl-L-cysteinyl-D-valine + ?
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UDP-N-acetylmuramoyl-L-Ala-D-Glu + L-Lys + ATP = UDP-N-acetylmuramoyl-L-Ala-D-Glu-L-Lys + ADP + phosphate
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2 ATP + 2 L-Val + L-Lys = 2 ADP + 2 phosphate + L-Val-L-Val-L-Lys
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ATP + H2O + lysine/out = ADP + phosphate + lysine/in
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Product in Enzyme-catalyzed Reactions (251 results)

EC NUMBER
REACTION
REACTION DIAGRAM
LITERATURE
ENZYME 3D STRUCTURE
epsilon-pyridoxyllysine 5'-phosphate + H2O + O2 = pyridoxal 5'-phosphate + lysine + H2O2
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N2-(D-1-carboxyethyl)-L-lysine + NADP+ + H2O = L-lysine + pyruvate + NADPH
show the reaction diagram
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-
N6-(L-1,3-dicarboxypropyl)-L-lysine + NAD+ + H2O = L-lysine + 2-oxoglutarate + NADH + H+
show the reaction diagram
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-
epsilon-N-methyl-L-lysine + acceptor + H2O = formaldehyde + L-lysine + reduced acceptor
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homoarginine + glycine = homoornithine + guanidinoacetate
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5-L-glutamyl-L-lysine + acceptor = L-lysine + 5-L-glutamyl-acceptor
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L-lysine ethyl ester + H2O = L-lysine + ethanol
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L-lysine methyl ester + H2O = L-lysine + methanol
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Ala-Lys + H2O = Ala + Lys
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L-lysyl 4-nitroanilide + H2O = L-lysine + 4-nitroaniline
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L-lysyl 4-nitroanilide + H2O = L-lysine + 4-nitroaniline
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L-Lys-4-nitroanilide + H2O = L-Lys + 4-nitroaniline
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L-Asp-L-Lys + H2O = L-Asp + L-Lys
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L-Val-L-Lys + H2O = L-valine + L-lysine
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L-Ala-gamma-D-Glu-L-Lys + H2O = L-Ala-D-Glu + L-Lys
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N-carbobenzoxy-Ala-Ala-Lys + H2O = N-carbobenzoxy-Ala-Ala + Lys
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N-[3-(2-Furylacryloyl)]-L-Ala-L-Lys + H2O = N-[3-(2-Furylacryloyl)]-L-Ala + L-Lys
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N-carboxybenzoyl-Ala-Lys + H2O = N-carboxybenzoyl-Ala + L-lysine
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2-aminobenzoyl-Phe-Arg-Lys + H2O = 2-aminobenzoyl-Phe-Arg + Lys
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pyroglutamyl-Lys + H2O = pyroglutamate + Lys
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Lys-2-naphthylamide + H2O = Lys + 2-naphthylamine
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Abz-TTKLKAAK(Dnp)-NH2 + H2O = Abz-TTKL + L-Lys + L-Ala + AK(Dnp)-NH2
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FVNQHLCGSHLVEALYVCGERGFFYTPKA + H2O = FVNQHLCGSH + Lys-Val-Glu-Ala + Lys + YVCGERGF + FYTPKA
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N-acetyl-L-lysine + H2O = acetate + L-lysine
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L-Lys beta-naphthylamide + H2O = Lys + beta-naphthylamine
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N-acetyllysine + H2O = acetate + lysine
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Nalpha-acetyl-L-lysine + H2O = L-lysine + acetate
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L-homoarginine + H2O = L-2,6-diaminohexanoate + urea
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D-lysine = L-lysine
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D-lysine = L-lysine
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D-lysine = L-lysine
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ATP + H2O + lysine/out = ADP + phosphate + lysine/in
show the reaction diagram
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Activator in Enzyme-catalyzed Reactions (21 results)

EC NUMBER
COMMENTARY
LITERATURE
ENZYME 3D STRUCTURE
nonsubstrate activator stimulating NADPh oxidation 3.9fold at 2 mM causing H2O2 formation, overview
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5 mM, 2.29fold activation
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increased activity after 10 min preincubation
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activator of the ornithine succinyltransferase activity
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stimulates activity on histone H4
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stimulation, 105% of non-stimulated activity
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this enzyme is strongly induced in vivo by growing Candida on L-lysine
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stimulates, stimulation pattern of MtrA is similar to that of MtrB
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addition of 16.2 mmol/l L-lysine give 3fold to 4fold enhancement of activation, which is further enhanced to 5fold to 6fold by addition of 2.86 microgram/ml oversulfated chondroitin-6-sulfate or oversulfated fucoidan
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induces enzyme
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30% activation at 20 mM
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activates
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mutagenesis of the lysine binding sites of the Corynebacterium glutamicum enzyme according to the residues in the Escherichia coli enzyme does not conver the expected feedback inhibition but an activation of the nezyme by L-lysine
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Inhibitor in Enzyme-catalyzed Reactions (169 results)

EC NUMBER
COMMENTARY
LITERATURE
ENZYME 3D STRUCTURE
mixed-type inhibition
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substrate inhibition of the wild-type and mutant P14G enzymes
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slight inhibition
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weak inhibition at pH 8.5, strong inhibition at pH 10.0
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; pH 7.6, 30°C
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the presence of L-lysine during the oxidation of benzylamine results in time- and dose-dependent inhibition of SSAO activity, in a process that is dependent on the H2O2 formed during benzylamine oxidation
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1 mM, 43% inhibition of DEAE-unabsorbed transglutaminase, 90% inhibition of DEAE-absorbed transglutaminase
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inhibition of alpha-S1-casein-dependent reaction
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about 80% residual activity at 0.5 mM
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1 mM, more than 80% reemaining activity
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35% inhibition at 10 mM after 20 min
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20% inhibition
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noncompetitive inhibition with respect to delta-aminovalerate, competitive inhibition to 2-oxoglutarate
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10 mM, 35% inhibition
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total and cytosolic creatine kinase activities are significantly inhibited by L-lysine, in contrast to the mitochondrial isoform which is not affected, the inhibitory effect of L-lysine on total creatine kinase activity is totally prevented by reduced glutathione
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slight inhibition of coaggregation of Porphyromonas gingivalis with other oral bacteria by L-lysine and more slightly by D-lysine
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38.5% residual activity at 5 mM
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competitive inhibitor; potential competitive inhibitor
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inhibition of the recombinant enzyme at high concentrations
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50% inhibition at 0.2 mM, inhibits wild-type enzyme, but not mutant enzymes
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1% cell growth, 1% viability of cells
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Enzyme Kinetic Parameters

kcat Value (Turnover Number) (134 results)

EC NUMBER
TURNOVER NUMBER [1/S]
TURNOVER NUMBER MAXIMUM [1/S]
COMMENTARY
LITERATURE
34.7
-
-
2.6
4.2
in synthetic peptides
203
-
at pH 7.5 and 70°C
0.000062
-
-
0.0036
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pH 8.5, 37°C
0.008
-
at pH 7.5 and 30°C
0.61
-
0.1 mM NAD+, in 100 mM HEPES (pH 8.0), at 30°C
4.17
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pH 8.0, 30°C, recombinant mutant I222T/Y354W
0.0013
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pH 8.5, 37°C, recombinant enzyme
0.07
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pH 7.8, 37°C

KM Value (259 results)

EC NUMBER
KM VALUE [MM]
KM VALUE MAXIMUM [MM]
COMMENTARY
LITERATURE
90
-
-
5.25
-
pH 7.0, 37°C
18.2
-
-
25
-
pH 8.5, 37°C
6.3
-
in mitochondrial extracts
4.24
-
-
2
-
pH 8.3, 37°C
50
-
-
1.518
-
-
0.3
-
at pH 7.5 and 30°C
32
-
pH 8.0, 30°C, recombinant mutant I222T/Y354W
2.8
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at 68°C
0.00736
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pH 4.5, 30°C, recombinant enzyme

Ki Value (54 results)

EC NUMBER
KI VALUE [MM]
KI VALUE MAXIMUM [MM]
COMMENTARY
LITERATURE
TABLE ID
0.09
-
-
2214
0.26
-
pH not specified in the publication, temperature not specified in the publication
2311
3.2
-
-
3610
2.5
-
pH 7.4
3403
0.0374
-
pH 7.2, 37°C
4309
37
-
-
9252
1.8
-
in 100 mM TEA-HCl pH 7.8, temperature not specified in the publication; pH 7.8, 25°C
35058

IC50 Value (20 results)

EC NUMBER
IC50 VALUE
IC50 VALUE MAXIMUM
COMMENTARY
LITERATURE

References & Links