Ligand L-methionine

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Basic Ligand Information

Molecular Structure
Picture of L-methionine (click for magnification)
Molecular Formula
BRENDA Name
InChIKey
C5H11NO2S
L-methionine
FFEARJCKVFRZRR-BYPYZUCNSA-N
Synonyms:
L-Met, L-methionine[side 2], Met, methionine, methionine[side 2]
Pathway Source
Pathways
BRENDA
1,4-dihydroxy-6-naphthoate biosynthesis, biotin biosynthesis, factor 420 biosynthesis, heme metabolism, kanamycin biosynthesis more
KEGG
2-Oxocarboxylic acid metabolism, Aminoacyl-tRNA biosynthesis, Antifolate resistance, Biosynthesis of amino acids, Biosynthesis of cofactors more
MetaCyc
(aminomethyl)phosphonate degradation, 1,4-dihydroxy-6-naphthoate biosynthesis I, 1,4-dihydroxy-6-naphthoate biosynthesis II, 2'-deoxymugineic acid phytosiderophore biosynthesis, 3,8-divinyl-chlorophyllide a biosynthesis II (anaerobic) more


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

Roles as Enzyme Ligand

In Vivo Substrate in Enzyme-catalyzed Reactions (19 results)

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EC NUMBER
PROVEN IN VIVO REACTION
REACTION DIAGRAM
LITERATURE
ENZYME 3D STRUCTURE
L-methionine + O2 = ? + H2O2
show the reaction diagram
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L-methionine + NADPH + O2 = L-methionine S-oxide + NADP+ + H2O
show the reaction diagram
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L-methionine + nicotinamide = L-homocysteine + 1-methylnicotinamide
show the reaction diagram
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S-adenosyl-L-methionine + L-methionine = S-adenosyl-L-homocysteine + S-methyl-L-methionine
show the reaction diagram
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5-deoxy-5-chloroadenosine + L-methionine = S-adenosyl-L-methionine + chloride
show the reaction diagram
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L-methionine + 2-oxoglutarate = 4-methylsulfanyl-2-oxobutanoate + L-glutamate
show the reaction diagram
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C-terminal [mycofactocin precursor peptide MftA]-glycyl-3-amino-5-[(4-hydroxyphenyl)methyl]-4,4-dimethylpyrrolidin-2-one + 5?-deoxyadenosine + L-methionine + A = C-terminal [mycofactocin precursor peptide]-glycyl-L-valyl-4-[2-aminoethenyl]phenol + S-adenosyl-L-methionine + AH2
show the reaction diagram
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L-methionine + H2O = methanethiol + NH3 + 2-oxobutanoate
show the reaction diagram
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L-Methionine = D-Methionine
show the reaction diagram
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ATP + L-methionine + an L-amino acid = ADP + phosphate + L-methionyl-L-amino acid
show the reaction diagram
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In Vivo Product in Enzyme-catalyzed Reactions (98 results)

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EC NUMBER
PROVEN IN VIVO REACTION
REACTION DIAGRAM
LITERATURE
ENZYME 3D STRUCTURE
dehypoxanthine futalosine + S-adenosyl-L-methionine = cyclic dehypoxanthine futalosine + 5'-deoxyadenosine + L-methionine
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a PqqA peptide + S-adenosyl-L-methionine = a PqqA peptide with linked Glu-Tyr residues + 5'-deoxyadenosine + L-methionine
show the reaction diagram
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Fe-coproporphyrin III + S-adenosyl-L-methionine = protoheme + CO2 + 5'-deoxyadenosine + L-methionine
show the reaction diagram
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C-terminal [mycofactocin precursor peptide MftA]-glycyl-L-valyl-L-tyrosine + S-adenosyl-L-methionine = C-terminal [mycofactocin precursor peptide MftA]-glycyl-L-valyl-4-[2-aminoethenyl]phenol + CO2 + 5'-deoxyadenosine + L-methionine
show the reaction diagram
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S-adenosyl-L-methionine + dihydroflavodoxin + [formate C-acetyltransferase]-glycine = 5'-deoxyadenosine + L-methionine + flavodoxin semiquinone + [formate C-acetyltransferase]-glycin-2-yl radical
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dimethylthetin + L-homocysteine = S-methylthioglycolate + L-methionine
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2 S-adenosyl-L-methionine + N-acetyldemethylphosphinothricin + reduced acceptor = S-adenosyl-L-homocysteine + 5'-deoxyadenosine + L-methionine + N-acetylphosphinothricin + oxidized acceptor
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2 S-adenosyl-L-methionine + protoheme + 2 reduced flavodoxin = S-adenosyl-L-homocysteine + L-methionine + 5'-deoxyadenosine + anaerobilin + Fe2+ + 2 oxidized flavodoxin
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S-adenosyl-L-methionine + 7-aminomethyl-7-deazaguanine in tRNA(Tyr) = L-methionine + adenine + epoxyqueuosine in tRNA(Tyr)
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5-amino-6-(D-ribitylamino)uracil + L-tyrosine + S-adenosyl-L-methionine = 5-amino-5-(4-hydroxybenzyl)-6-(D-ribitylimino)-5,6-dihydrouracil + 2-iminoacetate + L-methionine + 5'-deoxyadenosine
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O-acetyl-L-homoserine + methanethiol = L-methionine + acetate
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S-adenosyl-L-methionine + fluoride = 5'-deoxy-5'-fluoroadenosine + L-methionine
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S-adenosyl-L-methionine + H2O = adenosine + L-methionine + H+
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L-glutamine + 4-(methylsulfanyl)-2-oxobutanoate = 2-oxoglutaramate + L-methionine
show the reaction diagram
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7-N-[(5S)-5-amino-5-carboxypentyl]formamidino-7-deazaguanosine15 in tRNA + S-adenosyl-L-methionine = 5'-deoxyadenosine + archaeosine15 in tRNA + 2 H+ + L-1-piperideine-6-carboxylate + L-methionine
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N6-dimethylallyladenine37 in tRNA + sulfur-(sulfur carrier) + 2 S-adenosyl-L-methionine = 2-methylthio-N6-dimethylallyladenine37 in tRNA + S-adenosyl-L-homocysteine + (sulfur carrier) + L-methionine + 5'-deoxyadenosine
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N6-L-threonylcarbamoyladenine37 in tRNA + sulfur-(sulfur carrier) + 2 S-adenosyl-L-methionine = 2-methylthio-N6-L-threonylcarbamoyladenine37 in tRNA + S-adenosyl-L-homocysteine + (sulfur carrier) + L-methionine + 5'-deoxyadenosine
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Met-Leu + H2O = Met + Leu
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Met-peptide + H2O = Met + peptide
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N1-methylguanine37 in tRNAPhe + pyruvate + S-adenosyl-L-methionine = 4-demethylwyosine37 in tRNAPhe + L-methionine + 5'-deoxyadenosine + CO2 + H2O
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GTP + S-adenosyl-L-methionine + reduced electron acceptor = (8S)-3',8-cyclo-7,8-dihydroguanosine 5'-triphosphate + 5'-deoxyadenosine + L-methionine + oxidized electron acceptor
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5-amino-1-(5-phospho-beta-D-ribosyl)imidazole + S-adenosyl-L-methionine + reduced acceptor = 5-hydroxybenzimidazole + 5'-deoxyadenosine + L-methionine + formate + NH3 + phosphate + oxidized acceptor
show the reaction diagram
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C-terminal [mycofactocin precursor peptide]-glycyl-L-valyl-4-[2-aminoethenyl]phenol + S-adenosyl-L-methionine + AH2 = C-terminal [mycofactocin precursor peptide]-glycyl-3-amino-5-[(4-hydroxyphenyl)methyl]-4,4-dimethylpyrrolidin-2-one + 5'-deoxyadenosine + L-methionine + A
show the reaction diagram
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5-amino-5-(4-hydroxybenzyl)-6-(D-ribitylimino)-5,6-dihydrouracil + S-adenosyl-L-methionine = 7,8-didemethyl-8-hydroxy-5-deazariboflavin + NH3 + L-methionine + 5'-deoxyadenosine
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D-Met = L-Met
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ATP + H2O + L-methionine-[methionine-binding protein][side 1] = ADP + phosphate + L-methionine[side 2] + [methionine-binding protein][side 1]
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Substrate in Enzyme-catalyzed Reactions (180 results)

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EC NUMBER
REACTION
REACTION DIAGRAM
LITERATURE
ENZYME 3D STRUCTURE
L-methionine + O2 = ? + H2O2
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Met + Cl- + H2O2 = ?
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L-methionine + O2 = 3-(methylthio)propanamide + CO2 + H2O
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L-methionine + 2-oxoglutarate + O2 = L-methionine sulfoxide + succinate + CO2
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L-methionine + ? + O2 = ?
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L-methionine + H2O + NAD+ = 4-(methylsulfanyl)-2-oxobutanoate + NH3 + NADH
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L-methionine + H2O + NAD+ = ? + NH3 + NADH + H+
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L-methionine + H2O + NAD+ = (4-methylsulfanyl)-2-oxobutanoate + NH3 + NADH
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L-methionine + H2O + NAD+ = 4-(methylthio)-2-oxobutanoic acid + NH3 + NADH
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L-methionine + H2O + 2 cytochrome b = 4-methylsulfanyl-2-oxobutanoate + NH3 + 2 reduced cytochrome b
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L-Met + pyruvate + NADPH = N2-(D-1-Carboxyethyl)-L-Met + NADP+ + H2O
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L-methionine + pyruvate + NADH + H+ = ?
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L-Met + pyruvate + NADH = ?
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L-methionine + thioredoxin disulfide + H2O = L-methionine (R)-S-oxide + thioredoxin
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L-methionine + nicotinamide = L-homocysteine + 1-methylnicotinamide
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S-adenosyl-L-methionine + L-methionine = S-adenosyl-L-homocysteine + S-methyl-L-methionine
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acetyl-CoA + L-methionine = CoA + N-acetyl-L-methionine
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L-methionine + 2-oxoglutarate = L-glutamate + 4-methylsulfanyl-2-oxobutyric acid
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L-methionine + pyruvate = 4-methylthio-2-oxobutanoate + L-alanine
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L-methionine + 2-oxoglutarate = 4-methylsulfanyl-2-oxobutanoate + L-glutamate
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L-methionine + phenylpyruvate = 4-methylsulfanyl-2-oxobutanoate + L-phenylalanine
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L-methionine + 2-oxoglutarate = 4-methylsulfanyl-2-oxobutanoate + L-glutamate
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L-methionine + glyoxylate = 4-methylsulfanyl-2-oxobutanoate + glycine
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L-methionine + indole-3-pyruvic acid = 2-oxo-4-methylthiobutanoate + L-tryptophan
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L-methionine + 2-oxoglutarate = 4-(methylsulfanyl)-2-oxobutanoate + L-glutamate
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Leu + Met = substance P
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L-Met = 3-Methylmercaptopropylamine + CO2
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2-Oxobutanoate + L-Met = ?
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L-methionine = 3-(methylsulfanyl)propanamine + CO2
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L-methionine + H2O = 2-oxobutanoate + NH3 + ?
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L-Methionine = D-Methionine
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L-Methionine = D-Methionine
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L-Methionine = D-Methionine
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L-Met = D-Met
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ATP + L-methionine + tRNALeu = AMP + diphosphate + L-methionyl-tRNALeu
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ATP + L-methionine + tRNALys = AMP + L-methionyl-tRNALys + diphosphate
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2 ATP + 2 L-Val + L-Met = 2 ADP + 2 phosphate + L-Val-L-Val-L-Met
show the reaction diagram
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ATP + H2O + L-methionine/out = ADP + phosphate + L-methionine/in
show the reaction diagram
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Product in Enzyme-catalyzed Reactions (621 results)

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EC NUMBER
REACTION
REACTION DIAGRAM
LITERATURE
ENZYME 3D STRUCTURE
dehypoxanthine futalosine + S-adenosyl-L-methionine = cyclic dehypoxanthine futalosine + 5'-deoxyadenosine + L-methionine
show the reaction diagram
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a PqqA peptide + S-adenosyl-L-methionine = a PqqA peptide with linked Glu-Tyr residues + 5'-deoxyadenosine + L-methionine
show the reaction diagram
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C-terminal [mycofactocin precursor peptide MftA]-glycyl-L-valyl-L-tyrosine + S-adenosyl-L-methionine = C-terminal [mycofactocin precursor peptide MftA]-glycyl-L-valyl-4-[2-aminoethenyl]phenol + CO2 + 5'-deoxyadenosine + L-methionine
show the reaction diagram
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Fe-coproporphyrin III + S-adenosyl-L-methionine = protoheme + CO2 + 5'-deoxyadenosine + L-methionine
show the reaction diagram
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2-oxo-4-methylthiobutanoate + NH3 + NADH = L-Met + NAD+ + H2O
show the reaction diagram
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L-methionine sulfoxide + electron donor = L-methionine + oxidized electron donor + H2O
show the reaction diagram
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2 S-adenosyl-L-methionine + menaquinone-6 + reduced flavodoxin = S-adenosyl-L-homocysteine + L-methionine + 5'-deoxyadenosine + 8-methylmenaquinone-6 + oxidized flavodoxin
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5-L-glutamyl-L-Met + Gly-Gly = L-Met + 5-L-glutamyl-Gly-Gly
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5-amino-6-(D-ribitylamino)uracil + L-tyrosine + S-adenosyl-L-methionine = 5-amino-5-(4-hydroxybenzyl)-6-(D-ribitylimino)-5,6-dihydrouracil + 2-iminoacetate + L-methionine + 5'-deoxyadenosine
show the reaction diagram
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S-adenosyl-L-methionine + H2O = adenosine + L-methionine + H+
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L-asparagine + 4-methylsulfanyl-2-oxobutanoate = 2-oxosuccinamate + L-methionine
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L-glutamine + 4-methylsulfanyl-2-oxobutanoate = 2-oxoglutaramate + L-methionine
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L-alanine + 4-methylthio-2-oxobutyrate = pyruvate + L-methionine
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L-phenylalanine + 2-oxo-4-methylthiobutyrate = phenylpyruvate + L-methionine
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L-kynurenine + 4-methylsulfanyl-2-oxobutanoate = 4-(2-aminophenyl)-2,4-dioxobutanoate + L-methionine
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S-(4-bromophenyl)-L-cysteine + 4-methylsulfanyl-2-oxobutanoate = S-(4-bromophenyl)-3-thiopyruvate + methionine
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7-N-[(5S)-5-amino-5-carboxypentyl]formamidino-7-deazaguanosine15 in tRNA + S-adenosyl-L-methionine = 5'-deoxyadenosine + archaeosine15 in tRNA + 2 H+ + L-1-piperideine-6-carboxylate + L-methionine
show the reaction diagram
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N6-L-threonylcarbamoyladenine37 in tRNA + sulfur-(sulfur carrier) + 2 S-adenosyl-L-methionine = 2-methylthio-N6-L-threonylcarbamoyladenine37 in tRNA + S-adenosyl-L-homocysteine + (sulfur carrier) + L-methionine + 5'-deoxyadenosine
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L-methionine methyl ester + H2O = L-methionine + methanol
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[met5] enkephalins + H2O = Tyr + Met
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Met-amide + H2O = Met + NH3
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Met-Pro-Ala + H2O = Met + Pro-Ala
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L-methionyl 4-nitroanilide + H2O = L-methionine + 4-nitroaniline
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L-methionyl 4-nitroanilide + H2O = L-methionine + 4-nitroaniline
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L-methionyl 4-nitroanilide + H2O = L-methionine + 4-nitroaniline
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N-acetyl-L-methionine + H2O = L-Met + acetate
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Met-Met-Met + H2O = Met-Met + Met
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Met-Met-Met + H2O = Met-Met + Met
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benzyloxycarbonyl-Gly-Met + H2O = benzyloxycarbonyl-Gly + Met
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3-(2-furyl)acryloyl-L-Phe-L-Met + H2O = 3-(2-furyl)acryloyl-L-Phe + L-Met
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Benzyloxycarbonyl-Pro-Met + H2O = Benzyloxycarbonyl-Pro + Met
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benzyloxycarbonyl-Phe-Met + H2O = benzyloxycarbonyl-Phe + Met
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Met-Ala + H2O = Met + Ala
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L-Bz-Met + H2O = benzoic acid + L-methionine
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N-benzyloxycarbonyl-Ala-Met + H2O = N-benzyloxycarbonyl-Ala + L-methionine
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N-carboxybenzoyl-Ala-Met + H2O = N-carboxybenzoyl-Ala + L-methionine
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2-aminobenzoyl-Phe-Arg-Met + H2O = 2-aminobenzoyl-Phe-Arg + Met
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pyroglutamyl-Met + H2O = pyroglutamate + Met
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beta-Asp-Met + H2O = Asp + Met
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L-Met-4-nitroanilide + H2O = L-Met + 4-nitroaniline
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GLLVMLGL + H2O = GLLV + Met + LGL
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MDIGAYPHFMPTNLAGDPY + H2O = AYPHFMPTNLA + AYPHFMPTNLAGD + DIGAYPHFMPTNLAG + IGAYPHFMPTNLAGD + MDIGAYPHFMPTNL + MDIGAYPHFMPTNLA + MDIGAYPHFMPTNLAGD + MDIGAYPHFMPTNLAGDP + Met + MDIG + Met-Asp + Tyr + Pro-Tyr + GDPY + DPY
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MDIGAYPHFMPTNLAGDPY + H2O = YPHFMPTNL + AYPHFMPTNL + YPHFMPTNLA + AYPHFMPTNLAG + AYPHFMPTNLAGD + DIGAYPHFMPTNLA + DIGAYPHFMPTNLAG + YPHFMPTNLAGDPY + IGAYPHFMPTNLAGD + MDIG + MDIGA + Met-Asp + Met + Tyr + Pro-Tyr + GDPY + DPY
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Gly-Met + H2O = glycine + L-methionine
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L-methionine amide + H2O = L-methionine + NH3
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L-Met beta-naphthylamide + H2O = Met + beta-naphthylamine
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acetyl-methionine + H2O = methionine
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N-formyl-L-methionine + H2O = formate + L-methionine
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N-benzoylmethionine + H2O = benzoate + methionine
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L-methioninamide + H2O = L-methionine + NH3
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N-carbamoyl-L-methionine + H2O = L-methionine + CO2 + NH3
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N-acetyl-L-methionine + H2O = acetate + L-methionine
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DL-alpha-amino-4-methylthio butyronitrile + H2O = L-methionine + NH3
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N1-methylguanine37 in tRNAPhe + pyruvate + S-adenosyl-L-methionine = 4-demethylwyosine37 in tRNAPhe + L-methionine + 5'-deoxyadenosine + CO2 + H2O
show the reaction diagram
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L-tyrosine + S-adenosyl-L-methionine + reduced acceptor = 2-iminoacetate + 4-methylphenol + 5'-deoxyadenosine + L-methionine + acceptor + 2 H+
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5-amino-1-(5-phospho-beta-D-ribosyl)imidazole + S-adenosyl-L-methionine + reduced acceptor = 5-hydroxybenzimidazole + 5'-deoxyadenosine + L-methionine + formate + NH3 + phosphate + oxidized acceptor
show the reaction diagram
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C-terminal [mycofactocin precursor peptide]-glycyl-L-valyl-4-[2-aminoethenyl]phenol + S-adenosyl-L-methionine + AH2 = C-terminal [mycofactocin precursor peptide]-glycyl-3-amino-5-[(4-hydroxyphenyl)methyl]-4,4-dimethylpyrrolidin-2-one + 5'-deoxyadenosine + L-methionine + A
show the reaction diagram
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5-amino-5-(4-hydroxybenzyl)-6-(D-ribitylimino)-5,6-dihydrouracil + S-adenosyl-L-methionine = 7,8-didemethyl-8-hydroxy-5-deazariboflavin + NH3 + L-methionine + 5'-deoxyadenosine
show the reaction diagram
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5-L-glutamyl-L-methionine = 5-oxoproline + L-methionine
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D-methionine = L-methionine
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AMP + diphosphate + L-methionyl-tRNAMet = ATP + L-methionine + tRNAMet
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AMP + diphosphate + L-methionyl-tRNALys = ATP + L-methionine + tRNALys
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ATP + H2O + L-methionine/out = ADP + phosphate + L-methionine/in
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ATP + H2O + L-methionine-[methionine-binding protein][side 1] = ADP + phosphate + L-methionine[side 2] + [methionine-binding protein][side 1]
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ATP + H2O + methionine-[methionine-binding protein][side 1] = ADP + phosphate + methionine[side 2] + [methionine-binding protein][side 1]
show the reaction diagram
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Activator in Enzyme-catalyzed Reactions (35 results)

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EC NUMBER
COMMENTARY
LITERATURE
ENZYME 3D STRUCTURE
maximum activation at 10 mM
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5.8fold activation at 50 mM
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5 mM, 1.54fold activation
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stimulation, 114% of non-stimulated activity
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activation
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L-methionine enhances the enzyme activity in absence of tumor necrosis factor-alpha, but inhibits it in presence of TNF-alpha
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causes an increase in Vmax value and a decrease in Km value, nonessential mode of activation
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26% activation at 5 mM
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20% activation at 20 mM
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at 10 mM 112% activity, at 100 mM 111% activity
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stimulates
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activates
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Inhibitor in Enzyme-catalyzed Reactions (135 results)

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EC NUMBER
COMMENTARY
LITERATURE
ENZYME 3D STRUCTURE
complete inhibition at 0.05 mM, reversible by increasing I- concentration
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pH 7.6, 30°C
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10% inhibition at 250 mM, with dimethylglycine
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slight inhibition
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product inhibition above 0.5 mM
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30 mM, weak
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competitive
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weak
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uncompetitive inhibition versus 7-(aminomethyl)-7-deazaguanine-tRNATyr and noncompetitive inhibition against S-adenosyl-L-methionine
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weak inhibition
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2 mM, decreases the expression level of CGS
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57% inhibition at 5 mM, competitive inhibition
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10 mM methionine inhibits the activity with 1 mM tyrosine and phenylalanine by 86 and 59%, respectively, but it has no effect on the isoleucine activity
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10 mM, inhibits activity of isoenzyme ArAT-I with 1 mM tyrosine by 23%, isoenzyme ArAT-II is not affected
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10 mM: competitive inhibitor
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2 mM, slight
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product inhibition. The combination of both products in equimolar concentrations results in more than simple additive inhibition, suggesting that they bind cooperatively to the enzyme.
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L-methionine enhances the enzyme activaty in absence of tumor necrosis factor-alpha, but inhibits it in presence of TNF-alpha
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synthesis of the enzyme is repressed
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noncompetitive with Ala-2-naphthylamide
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form I inhibited, form II slightly activated
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inhibition at 10 and 50 mM, in the presence of 0.1 mM MnCl2
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20% inhibition at 20 mM
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inhibits enzyme form CSAD I and CSAD II
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cooperative inhibition by with 5'-deoxyadenosine
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at 10 or 100 mM 80% residual activity
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weak
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less effective inhibitor, Ki-value above 150 mM
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selenomethionyl-tRNA formation
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enzyme YtmJKLMN shows 40% inhibition at 0.05 mM
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Enzyme Kinetic Parameters

kcat Value (Turnover Number) (137 results)

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EC NUMBER
TURNOVER NUMBER [1/S]
TURNOVER NUMBER MAXIMUM [1/S]
COMMENTARY
LITERATURE
0.00155
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33
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at pH 7.0 and 34°C
2.11
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in 100 mM glycine-KCl-KOH buffer (pH 10.4)
0.2
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in 50 mM phosphate buffer (pH 7.9) at 37°C
17
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pH 8.0, 25°C
1200
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pH 8.0, 25°C
0.0859
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pH 7.5, 37°C, recombinant enzyme
0.015
-
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0.00097
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pH 7.0, 35°C