Information on EC 4.4.1.11 - methionine gamma-lyase

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The expected taxonomic range for this enzyme is: Bacteria, Eukaryota, Archaea

EC NUMBER
COMMENTARY hide
4.4.1.11
-
RECOMMENDED NAME
GeneOntology No.
methionine gamma-lyase
REACTION
REACTION DIAGRAM
COMMENTARY hide
ORGANISM
UNIPROT
LITERATURE
L-methionine + H2O = methanethiol + NH3 + 2-oxobutanoate
show the reaction diagram
REACTION TYPE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
elimination
-
-
alpha,gamma and alpha,beta-elimination; gamma-replacement; of H2S or RSH, C-S bond cleavage
-
PATHWAY
BRENDA Link
KEGG Link
MetaCyc Link
Cysteine and methionine metabolism
-
-
methionine metabolism
-
-
Selenocompound metabolism
-
-
SYSTEMATIC NAME
IUBMB Comments
L-methionine methanethiol-lyase (deaminating; 2-oxobutanoate-forming)
A pyridoxal-phosphate protein. The enzyme cleaves a carbon-sulfur bond, releasing methanethiol and an unstable enamine product that tautomerizes to an imine form, which undergoes a hydrolytic deamination to form 2-oxobutanoate and ammonia. The latter reaction, which can occur spontaneously, can also be catalysed by EC 3.5.99.10, 2-iminobutanoate/2-iminopropanoate deaminase. The enzyme is involved in L-methionine catabolism.
CAS REGISTRY NUMBER
COMMENTARY hide
42616-25-1
-
ORGANISM
COMMENTARY hide
LITERATURE
UNIPROT
SEQUENCE DB
SOURCE
Achromobacter starkeyi
-
-
-
Manually annotated by BRENDA team
variant Aspergillus flavus columnaris
-
-
Manually annotated by BRENDA team
-
-
-
Manually annotated by BRENDA team
-
-
-
Manually annotated by BRENDA team
-
-
-
Manually annotated by BRENDA team
-
-
-
Manually annotated by BRENDA team
ATCC29063
SwissProt
Manually annotated by BRENDA team
-
-
-
Manually annotated by BRENDA team
-
-
-
Manually annotated by BRENDA team
-
-
-
Manually annotated by BRENDA team
strain JCM8532
-
-
Manually annotated by BRENDA team
Fusobacterium nucleatum subsp. nucleatum, ATCC 25586
-
UniProt
Manually annotated by BRENDA team
-
-
-
Manually annotated by BRENDA team
-
-
-
Manually annotated by BRENDA team
strain IL1403
-
-
Manually annotated by BRENDA team
-
-
-
Manually annotated by BRENDA team
no activity in mammalia
-
-
-
Manually annotated by BRENDA team
strain PAO1
-
-
Manually annotated by BRENDA team
-
-
-
Manually annotated by BRENDA team
strain S-313
-
-
Manually annotated by BRENDA team
cv. Desiree, gene StMGL1
-
-
Manually annotated by BRENDA team
strain ATCC35405
-
-
Manually annotated by BRENDA team
additional information
-
-
-
Manually annotated by BRENDA team
GENERAL INFORMATION
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
evolution
-
the enzyme belongs to the subclass of cystathionine beta-lyase with type I folding of the polypeptide chain of pyridoxal 5'-phosphate-dependent enzymes
malfunction
-
in planta silencing of StMGL1 results in an increased methionine to isoleucine ratio in the free amino acid profile of potato tubers and, in some transgenic lines, elevated accumulation of free methionine. In both wild-type and transgenic tubers, the ratio of methionine to isoleucine is negatively correlated with the level of StMGL1 transcript
metabolism
physiological function
additional information
SUBSTRATE
PRODUCT                       
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate) hide
LITERATURE
(Substrate)
COMMENTARY
(Product) hide
LITERATURE
(Product)
Reversibility
r=reversible
ir=irreversible
?=not specified
1-amino-3-(methylthio)propylphosphinic acid + H2O
1-oxopropylphosphinic acid + methanethiol + NH3
show the reaction diagram
-
-
-
?
2-amino-3-(N,N-dimethylamino)propionic acid
2-iminopropionic acid + ?
show the reaction diagram
-
C-N-bond cleavage
-
?
beta-(S-ethyl-L-cysteine)
?
show the reaction diagram
Arg374 and Ser339 are involved in the binding of carboxyl groups of the substrate, the hydroxyl of Tyr113 is a potential acceptor of a proton from the amino groups of the amino acid. Formation of external aldimine, conformational changes in the active center enable the Tyr58 hydroxyl group to occupy a position favorable for protonation of the leaving group
-
-
?
beta-chloro-L-alanine + H2O
?
show the reaction diagram
-
-
-
-
?
cystathionine + ?
?
show the reaction diagram
-
-
-
-
?
DL-2-amino-3-(N-hydroxyethylamino)-propionic acid
ethanolamine + NH3 + pyruvate
show the reaction diagram
-
-
-
?
DL-2-amino-3-(N-methylamino)propionic acid
methylamine + NH3 + pyruvate
show the reaction diagram
-
-
-
?
DL-ethionine + H2O
?
show the reaction diagram
-
-
-
-
?
DL-homocysteic acid + H2O
?
show the reaction diagram
-
-
-
-
?
DL-homocysteine + H2O
2-oxobutanoate + NH3 + H2S
show the reaction diagram
DL-homocysteine + H2O
?
show the reaction diagram
DL-homocysteine + H2O
H2S + S-(beta-hydroxyethyl)-L-homocysteine
show the reaction diagram
-
gamma-replacement reaction, wild-type enzyme
-
-
?
DL-homocysteine + H2O
hydrogen sulfide + NH3 + 2-oxobutanoate
show the reaction diagram
DL-homoserine + H2O
NH3 + 2-oxobutanoate
show the reaction diagram
-
-
-
-
?
ethionine
?
show the reaction diagram
gamma-(L-1-amino-3-methylthiopropylphosphinic acid)
?
show the reaction diagram
Arg374 and Ser339 are involved in the binding of carboxyl groups of the substrate, the hydroxyl of Tyr113 is a potential acceptor of a proton from the amino groups of the amino acid
-
-
?
homocysteine + alkanethiol
S-alkylhomocysteine
show the reaction diagram
-
-
corresponding
?
L-cystathionine + ?
?
show the reaction diagram
-
-
-
-
?
L-cystathionine + H2O
?
show the reaction diagram
L-cysteine
2-oxopropanoate + NH3 + H2S
show the reaction diagram
-
-
-
-
?
L-cysteine
?
show the reaction diagram
L-cysteine + H2O
?
show the reaction diagram
L-cysteine + H2O
H2S + S-(beta-hydroxyethyl)-L-cysteine
show the reaction diagram
-
beta-replacement reaction, wild-type enzyme and mutant C116H
-
-
?
L-cysteine + H2O
sulfide + NH3 + pyruvate
show the reaction diagram
L-cystine + H2O
?
show the reaction diagram
assay at pH 8.0, 37C
-
-
?
L-ethionine + H2O
?
show the reaction diagram
L-ethionine + H2O
ethanethiol + NH3 + 2-oxobutanoate
show the reaction diagram
L-Gly(vinyl) + H2O
?
show the reaction diagram
-
-
-
-
?
L-homocysteine
2-oxobutanoate + NH3 + hydrogen sulfide
show the reaction diagram
L-homocysteine + H2O
?
show the reaction diagram
L-homocysteine + H2O
hydrogen sulfide + NH3 + 2-oxobutanoate
show the reaction diagram
L-homoserine
NH3 + 2-oxobutanoate
show the reaction diagram
-
-
-
?
L-homoserine + H2O
?
show the reaction diagram
L-methionine
?
show the reaction diagram
L-methionine
methanethiol + NH3 + 2-oxobutanoate
show the reaction diagram
L-methionine + 2-butylthiol
S-2-butylhomocysteine
show the reaction diagram
-
-
-
?
L-methionine + 2-mercaptoethanol
methanethiol + S-(beta-hydroxyethyl)-L-homocysteine
show the reaction diagram
-
gamma-replacement reaction, wild-type enzyme
-
-
?
L-methionine + 2-propylthiol
S-2-propylhomocysteine
show the reaction diagram
-
-
-
?
L-methionine + H2O
?
show the reaction diagram
L-methionine + H2O
methanethiol + NH3 + 2-oxobutanoate
show the reaction diagram
L-methionine sulfone
?
show the reaction diagram
L-methionine sulfoxide
?
show the reaction diagram
-
-
-
-
?
L-methionine sulfoxide + H2O
?
show the reaction diagram
L-selenodjenkolate
pyruvate + NH3 + H2Se + formaldehyde
show the reaction diagram
-
-
-
?
L-selenomethionine + H2O
?
show the reaction diagram
-
-
-
-
?
L-vinylglycine
?
show the reaction diagram
O-acetyl-DL-homoserine + H2O
NH3 + 2-oxobutanoate + acetate
show the reaction diagram
-
-
-
-
?
O-acetyl-L-homoserine
?
show the reaction diagram
-
-
-
?
O-acetyl-L-homoserine + H2O
?
show the reaction diagram
-
-
-
-
?
O-acetyl-L-serine + H2O
2-oxopropanoate + NH3 + acetate
show the reaction diagram
O-succinyl-L-homoserine + H2O
?
show the reaction diagram
-
weak activity
-
-
?
S-benzyl-L-cysteine + H2O
?
show the reaction diagram
S-benzyl-L-cysteine + H2O
thiobenzyl alcohol + NH3 + 2-oxopropanoate
show the reaction diagram
S-ethyl-L-cysteine
?
show the reaction diagram
-
-
-
?
S-ethyl-L-cysteine + H2O
?
show the reaction diagram
S-ethyl-L-cysteine + H2O
ethanethiol + NH3 + 2-oxopropanoate
show the reaction diagram
S-ethyl-L-homocysteine + H2O
?
show the reaction diagram
S-ethyl-L-homocysteine + H2O
ethanethiol + NH3 + 2-oxobutanoate
show the reaction diagram
-
-
-
-
?
S-methyl-L-cysteine
?
show the reaction diagram
-
-
-
?
S-methyl-L-cysteine + 2-mercaptoethanol
?
show the reaction diagram
-
-
-
-
?
S-methyl-L-cysteine + H2O
?
show the reaction diagram
-
-
-
-
?
S-methyl-L-cysteine + H2O
methanethiol + NH3 + 2-oxopropanoate
show the reaction diagram
S-methyl-L-cysteine + H2O
pyruvate + NH3 + CH3SH
show the reaction diagram
S-methylcysteine + H2O
?
show the reaction diagram
-
-
-
-
?
Se-methylselenocysteine
?
show the reaction diagram
selenoethionine + H2O
ethylselenol + NH3 + 2-oxobutanoate
show the reaction diagram
-
-
-
?
selenomethionine + H2O
methylselenol + NH3 + 2-oxobutanoate
show the reaction diagram
trifluoromethionine + H2O
?
show the reaction diagram
-
-
-
-
?
trifluoromethionine + H2O
trifluoromethanethiol + NH3 + 2-oxobutanoate
show the reaction diagram
-
-
-
?
L-methionine
?
show the reaction diagram
NATURAL SUBSTRATES
NATURAL PRODUCTS
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate) hide
LITERATURE
(Substrate)
COMMENTARY
(Product) hide
LITERATURE
(Product)
REVERSIBILITY
r=reversible
ir=irreversible
?=not specified
L-homocysteine
2-oxobutanoate + NH3 + hydrogen sulfide
show the reaction diagram
L-methionine
?
show the reaction diagram
L-methionine + H2O
methanethiol + NH3 + 2-oxobutanoate
show the reaction diagram
L-methionine
?
show the reaction diagram
additional information
-
bacterial metabolism of methionine
-
-
-
COFACTOR
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
pyridoxal 5'-phosphate
METALS and IONS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
Na+
-
significant enzyme inhibition
Ni2+
-
slightly stimulatory effect on the enzyme activity
INHIBITORS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
2-mercaptoethanol
3-Methyl-2-benzothiazolinone hydrazone
-
-
3-methyl-2-benzothiazonlinone hydrazone
-
1 mM, 23.6% residual activity
5,5'-dithiobis(2-nitrobenzoic acid)
5-5'-dithiobis-(2-nitrobenzoic acid)
aminoethyloxyvinylglycine
Carbonyl reagents
cycloserine
-
-
DL-Penicillamine
DL-propargylglycine
glycine
hydroxylamine
iodacetamide
-
-
iodoacetamide
iodoacetate
iodoacetic acid
L-2-amino-4-chloro-4-pentenoate
-
complete inhibition at 5 mol per mol of tetramer enzyme
L-2-aminobutanoate
-
-
L-Cycloserine
L-norleucine
L-norvaline
-
-
L-Vinylglycine
-
microspectrophotometric measurements
myrsinoic acid B
N-ethylmaleimide
NaCl
-
0.4% wt/vol, 78% residual activity
p-chloromercuri-benzoic acid
p-chloromercuribenzoate
p-chloromercuribenzoic acid
-
-
Penicillamine
propargylglycine
Semicarbazide
Sodium arsenate
Achromobacter starkeyi
-
-
Sodium azide
-
-
Sulfhydryl inhibitors
additional information
ACTIVATING COMPOUND
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
EDTA
-
1 mM, 115% of initial activity
KM VALUE [mM]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
1.25
1-amino-3-(methylthio)propylphosphinic acid
-
30C
18.2
2-amino-3-(N,N-dimethylamino)propionic acid
-
-
0.17
beta-(S-ethyl-L-cysteine)
-
pH and temperature not specified in the publication
-
3.6 - 22.3
cysteine
12.3
DL-2-amino-3(N-hydroxyethyl)propionic acid
-
-
2.3
DL-amino-3-(N-methylamino)propionic acid
-
-
0.2 - 6
DL-homocysteine
56.5
DL-homoserine
1.2
gamma-(L-1-amino-3-methylthiopropylphosphinic acid)
-
pH and temperature not specified in the publication
-
0.27
L-cystathionine
-
-
0.12 - 3.6
L-cysteine
0.2 - 37.2
L-ethionine
6.7
L-Gly(vinyl)
-
30C, pH 8.0
6.43
L-homocysteine
-
-
30
L-homoserine
0.0013 - 90
L-methionine
4 - 8.22
L-Methionine sulfone
6.2 - 33.51
L-methionine sulfoxide
2.3
L-selenodjenkolate
-
-
6.7 - 7.22
L-Vinylglycine
5.82
O-acetyl-DL-homoserine
-
pH 8.0, 30C
2.22
O-acetyl-L-homoserine
-
37C, pH 8.0
6.28 - 52.33
O-acetyl-L-serine
2.8
O-methyl-L-serine
-
-
0.18 - 1.47
S-Benzyl-L-cysteine
0.17 - 2.17
S-ethyl-L-cysteine
0.278 - 0.93
S-ethyl-L-homocysteine
0.17
S-etyhl-L-cysteine
recombinant enzyme
0.4 - 2.1
S-methyl-L-cysteine
0.77
S-methylcysteine
-
-
0.13
Se-methyl-L-selenocysteine
-
-
0.1 - 5.45
trifluoromethionine
additional information
L-methionine
TURNOVER NUMBER [1/s]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.057 - 71
DL-homocysteine
0.5 - 0.52
DL-homoserine
0.43 - 43.8
L-cysteine
0.017 - 33.4
L-ethionine
1.9
L-Gly(vinyl)
Citrobacter freundii
-
30C, pH 8.0
1.4
L-homoserine
Pseudomonas putida
-
-
0.03 - 48.6
L-methionine
2.1 - 40.4
L-Methionine sulfone
2.5 - 6.7
L-methionine sulfoxide
1.9 - 44.4
L-Vinylglycine
2.1
O-acetyl-DL-homoserine
Citrobacter freundii
-
pH 8.0, 30C
78
O-acetyl-L-homoserine
Pseudomonas putida
-
37C, pH 8.0
1.74 - 6.22
O-acetyl-L-serine
5.8 - 10.9
S-Benzyl-L-cysteine
5 - 8.05
S-ethyl-L-cysteine
3.84 - 7.05
S-ethyl-L-homocysteine
0.12 - 46.3
S-methyl-L-cysteine
0.24 - 17.46
trifluoromethionine
additional information
L-methionine
kcat/KM VALUE [1/mMs-1]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
6.29 - 64.5
DL-homocysteine
0.01
DL-homoserine
Citrobacter freundii
-
pH 8.0, 30C
6515
1.06 - 77.7
L-cysteine
0.01 - 66.8
L-methionine
0.52
L-Methionine sulfone
Citrobacter freundii
-
pH 8.0, 30C
3081
0.2 - 0.413
L-methionine sulfoxide
0.28
L-Vinylglycine
Citrobacter freundii
-
pH 8.0, 30C
2204
0.36
O-acetyl-DL-homoserine
Citrobacter freundii
-
pH 8.0, 30C
41724
3.94 - 28.7
S-Benzyl-L-cysteine
3.71 - 17.6
S-ethyl-L-cysteine
4.13 - 25.4
S-ethyl-L-homocysteine
0.3 - 22
S-methyl-L-cysteine
Ki VALUE [mM]
INHIBITOR
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE