Information on EC 4.4.1.13 - cysteine-S-conjugate beta-lyase

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

EC NUMBER
COMMENTARY hide
4.4.1.13
-
RECOMMENDED NAME
GeneOntology No.
cysteine-S-conjugate beta-lyase
REACTION
REACTION DIAGRAM
COMMENTARY hide
ORGANISM
UNIPROT
LITERATURE
2-aminoprop-2-enoate = 2-iminopropanoate
show the reaction diagram
spontaneous
-
-
-
2-iminopropanoate + H2O = pyruvate + NH3
show the reaction diagram
spontaneous
-
-
-
an L-cysteine-S-conjugate + H2O = a thiol + NH3 + pyruvate
show the reaction diagram
an L-cysteine-S-conjugate = a thiol + 2-aminoprop-2-enoate
show the reaction diagram
(1a)
-
-
-
REACTION TYPE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
elimination
-
-
of H2S or RSH, C-S bond cleavage
-
transamination
additional information
PATHWAY
BRENDA Link
KEGG Link
MetaCyc Link
glutathione-mediated detoxification I
-
-
glutathione-mediated detoxification II
-
-
Selenocompound metabolism
-
-
SYSTEMATIC NAME
IUBMB Comments
L-cysteine-S-conjugate thiol-lyase (deaminating; pyruvate-forming)
A pyridoxal-phosphate protein. The enzyme can act on a broad range of L-cysteine-S-conjugates, including aromatic conjugates such as 4-bromobenzene and 2,4-dinitrobenzene. The enzyme cleaves a carbon-sulfur bond, releasing a thiol and an unstable enamine product that tautomerizes to an imine form, which undergoes a hydrolytic deamination to form pyruvate and ammonia. The latter reaction, which can occur spontaneously, can also be catalysed by EC 3.5.99.10, 2-iminobutanoate/2-iminopropanoate deaminase.
CAS REGISTRY NUMBER
COMMENTARY hide
68652-57-3
-
ORGANISM
COMMENTARY hide
LITERATURE
UNIPROT
SEQUENCE DB
SOURCE
-
-
-
Manually annotated by BRENDA team
strain IFM
-
-
Manually annotated by BRENDA team
strain IFM
-
-
Manually annotated by BRENDA team
-
-
-
Manually annotated by BRENDA team
strain IFM
-
-
Manually annotated by BRENDA team
strain IFM
-
-
Manually annotated by BRENDA team
strain IFM
-
-
Manually annotated by BRENDA team
strain IFM
-
-
Manually annotated by BRENDA team
-
-
-
Manually annotated by BRENDA team
-
-
-
Manually annotated by BRENDA team
Monieza expansa
tapeworm
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-
Manually annotated by BRENDA team
-
-
-
Manually annotated by BRENDA team
-
-
-
Manually annotated by BRENDA team
-
-
-
Manually annotated by BRENDA team
strain DSM 20701
-
-
Manually annotated by BRENDA team
-
-
-
Manually annotated by BRENDA team
GENERAL INFORMATION
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
malfunction
metabolism
SUBSTRATE
PRODUCT                       
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate) hide
LITERATURE
(Substrate)
COMMENTARY
(Product) hide
LITERATURE
(Product)
Reversibility
r=reversible
ir=irreversible
?=not specified
(H2N)2Pt(Cl)SCH2CH(NH3+)CO2- + H2O
CH3C(O)CO2- + NH4+ + (NH2)2Pt(Cl)SH
show the reaction diagram
(S)-1,1,2,2-tetrafluoroethyl-L-cysteine + H2O
? + NH3 + pyruvate
show the reaction diagram
-
-
-
-
?
(S)-2,4-dinitrophenyl-L-cysteine
2,4-dinitrobenzenethiol + pyruvate + NH3
show the reaction diagram
(S)-2,4-dinitrophenyl-L-homocysteine
?
show the reaction diagram
(S)-2-benzothiazolyl-L-cysteine
pyruvate + NH3 + 2-mercaptobenzothiazole
show the reaction diagram
(S)-2-benzothiazolyl-L-cysteine + H2O
pyruvate + NH3 + 2-mercaptobenzothiazole
show the reaction diagram
-
-
-
-
?
(S)-4-bromophenyl-L-cysteine
p-bromobenzenethiol + NH3 + pyruvate
show the reaction diagram
(S)-4-nitrobenzyl-L-cysteine
?
show the reaction diagram
-
-
-
-
?
(S)-methylcysteine + H2O
methanethiol + pyruvate + NH3
show the reaction diagram
2-(2-(S)-L-cysteinylpentyl)-1,3-thiazolidine-4-carboxylic acid
3-mercaptohexanal + ?
show the reaction diagram
-
-
-
?
3-cysteinylhexanol
3-mercaptohexanal + ?
show the reaction diagram
3-hydroxykynurenine
?
show the reaction diagram
3-S-(N-acetyl-L-cysteinyl)-hexanal
3-mercaptohexanal + ?
show the reaction diagram
3-S-L-cysteinylhexanal
3-mercaptohexanal + ?
show the reaction diagram
4,5-epoxy-4,5-dihydro-1-nitropyrene
?
show the reaction diagram
-
-
-
-
?
5'-S-cysteinyldopamine
?
show the reaction diagram
-
-
-
-
?
5-S-L-cysteinyldopamine
pyruvate + ?
show the reaction diagram
-
slow beta-elimination reaction
-
-
?
8-S-cysteinyl-p-menthan-3-one
8-mercapto-p-menthan-3-one
show the reaction diagram
-
-
-
?
9,10-epoxy-9,10-dihydro-1-nitropyrene
?
show the reaction diagram
-
-
-
-
?
alanine derivatives
?
show the reaction diagram
-
-
-
-
?
alpha-keto-gamma-methiobutyric acid + L-aspartate
?
show the reaction diagram
Monieza expansa
-
transamination reaction
-
?
benzothiazolyl-L-cysteine
?
show the reaction diagram
beta-chloro-DL-alanine
?
show the reaction diagram
-
-
-
-
?
beta-chloro-L-alanine
?
show the reaction diagram
-
-
-
?
beta-chloroalanine
?
show the reaction diagram
-
-
-
-
?
cysteine thioethers
?
show the reaction diagram
-
-
-
-
?
kynurenine
?
show the reaction diagram
L-alanine
?
show the reaction diagram
L-aspartate
?
show the reaction diagram
L-cysteine conjugates
?
show the reaction diagram
L-leucine + alpha-ketoglutarate
?
show the reaction diagram
-
-
-
?
L-selenomethionine
HSe(CH3) + NH3 + 2-oxobutanoate
show the reaction diagram
-
-
-
?
leukotriene E4
?
show the reaction diagram
-
-
-
-
?
p-nitrobenzyl-L-cysteine
?
show the reaction diagram
RS-CH2-CH(NH3+)COO- + H2O
RSH + NH3 + pyruvate
show the reaction diagram
RSH-CH2-CH(NH3+)COO-
RSH + NH3 + pyruvate
show the reaction diagram
RSH-CH2-CH(NH3+)COO- + H2O
RSH + NH3 + pyruvate
show the reaction diagram
-
-
-
-
?
S-(1,1,2,2-tetrafluoroethyl)-L-cysteine
?
show the reaction diagram
S-(1,1,2,2-tetrafluoroethyl)-L-cysteine
NH3 + pyruvate + 1,1,2,2-tetrafluoroethanethiol
show the reaction diagram
-
-
-
-
?
S-(1,1,2,2-tetrafluoroethyl)-L-cysteine + H2O
NH3 + pyruvate + 1,1,2,2-tetrafluoroethanethiol
show the reaction diagram
-
-
-
-
ir
S-(1,1,2-trichlorovinyl)-L-cysteine
?
show the reaction diagram
Monieza expansa
-
-
-
?
S-(1,2-dichloroethenyl)-L-cysteine
pyruvate + NH3 + dichlorovinyl mercaptane
show the reaction diagram
-
-
-
-
?
S-(1,2-dichlorovinyl)-L-cysteine
?
show the reaction diagram
S-(1,2-dichlorovinyl)-L-cysteine + H2O
NH3 + pyruvate + 1,2-dichloroethylenethiol
show the reaction diagram
S-(2-chloro-1,1,2-trifluoroethyl)-L-cysteine
?
show the reaction diagram
S-(E-1,2-Dichlorovinyl)-L-cysteine
?
show the reaction diagram
S-(p-bromophenyl)-L-cysteine
?
show the reaction diagram
-
-
-
?
S-(p-bromophenyl)-L-cysteine
p-bromobenzenethiol + NH3 + pyruvate
show the reaction diagram
-
-
-
?
S-1,2-dichlorovinyl-L-cysteine + H2O
dichlorovinyl mercaptane + NH3 + pyruvate
show the reaction diagram
-
-
-
-
?
S-1,2-dichlorovinyl-L-cysteine + H2O
pyruvate + NH3 + dichlorovinyl mercaptane
show the reaction diagram
-
-
-
-
?
S-4-(4-methylpentan-2-one)-L-cysteine + H2O
4-mercapto-4-methylpentan-2-one + NH3 + pyruvate
show the reaction diagram
-
-
-
-
?
S-alkyl cysteines
?
show the reaction diagram
-
-
-
-
?
S-allyl-L-cysteine + H2O
NH3 + pyruvate + prop-2-ene-1-thiol
show the reaction diagram
-
-
-
-
ir
S-allylmercapto-L-cysteine + H2O
NH3 + pyruvate + allyl hydrodisulfide
show the reaction diagram
-
-
-
-
ir
S-Aralkyl cysteines
?
show the reaction diagram
-
-
-
-
?
S-methylmercapto-L-cysteine + H2O
NH3 + pyruvate + methanethiol
show the reaction diagram
-
-
-
-
ir
S-penta-1,3-dienylmercapto-L-cysteine + H2O
NH3 + pyruvate + penta-1,3-dien-1-yl hydrodisulfide
show the reaction diagram
-
-
-
-
ir
S-propylmercapto-L-cysteine + H2O
NH3 + pyruvate + propyl hydrodisulfide
show the reaction diagram
-
-
-
-
ir
S-[2-(fluoromethoxy)-1,1,3,3,3-pentafluoropropyl]-L-cysteine
pyruvate + ?
show the reaction diagram
-
-
-
?
S-[2-(fluoromethoxy)-1,3,3,3-tetrafluoropropyl]-L-cysteine
pyruvate + ?
show the reaction diagram
-
-
-
?
Se-(4-methylbenzyl)-L-selenocysteine
?
show the reaction diagram
-
-
-
?
Se-(allyl)-L-selenocysteine
?
show the reaction diagram
-
-
-
?
Se-(isopropyl)-L-selenocysteine
?
show the reaction diagram
-
-
-
?
Se-(phenyl)-L-selenocysteine
?
show the reaction diagram
-
-
-
?
Se-4-methoxybenzylselenocysteine + H2O
HSe(4-(CH3O)C6H4CH2) + pyruvate + NH3
show the reaction diagram
Se-methyl-L-selenocysteine
?
show the reaction diagram
-
-
-
-
?
Se-methyl-L-selenocysteine + H2O
HSe(CH3) + pyruvate + NH3
show the reaction diagram
-
-
-
?
Se-methylselenocysteine + H2O
HSe(CH3) + pyruvate + NH3
show the reaction diagram
Te-phenyl-L-tellurocysteine + H2O
NH3 + pyruvate + phenyltelluride
show the reaction diagram
-
-
-
-
ir
thioethers
?
show the reaction diagram
xenobiotics
thiol + pyruvate + NH3
show the reaction diagram
-
-
-
?
additional information
?
-
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
RS-CH2-CH(NH3+)COO- + H2O
RSH + NH3 + pyruvate
show the reaction diagram
-
-
-
-
ir
additional information
?
-
COFACTOR
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
pyridoxal 5'-phosphate
additional information
-
no cofactor requirement
-
METALS and IONS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
additional information
INHIBITORS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
3-hydroxykynurenine
-
cysteine conjugate beta-lyase activity
aminooxyacetic acid
aminooxyacetic acid hemihydrochloride
hydroxylamine
kynurenine
-
cysteine conjugate beta-lyase activity
N-acetyl-L-cysteine
-
-
p-chloromercuribenzoate
additional information
-
not: thiol blocking agents, EDTA
-
ACTIVATING COMPOUND
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
alpha-keto-gamma-methiobutyrate
-
stimulates
alpha-keto-gamma-methiolbutyrate
-
-
alpha-ketoglutarate
-
activates
additional information
-
several other alpha-keto acids also stimulate
-
KM VALUE [mM]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.5
2,4-dinitrophenyl-L-cysteine
0.013
3-hydroxy-kynurenine
-
-
0.6
beta-chloro-L-alanine
-
-
2.6
beta-chloroalanine
-
-
0.4
kynurenine
-
-
8.4
S-(1,1,2,2-tetrafluoroethyl)-L-cysteine
-
23°C, pH 7.4
1.36 - 1.39
S-(1,2-dichlorovinyl)-L-cysteine
0.01 - 1.66
S-(2-benzothiazolyl)-L-cysteine
1.02 - 1.78
S-(2-chloro-1,1,2-trifluoroethyl)-L-cysteine
0.7
S-(p-bromophenyl)-L-cysteine
-
-
0.1 - 0.33
S-1,2-dichlorovinyl-L-cysteine
0.08
S-2,4-dinitrophenyl-L-cysteine
-
-
additional information
additional information
-
kinetic parameters for differentially substituted cysteine-S-conjugates and selenocysteine Se-conjugates
-
SPECIFIC ACTIVITY [µmol/min/mg]
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
0.037
Monieza expansa
-
-
0.163
substrate Se-methyl-L-selenocysteine, pH 7.2, 37°C
0.47
-
in absence of 2-oxo-4-methylthiobutyric acid
2.15
substrate L-selenomethionine, pH 7.2, 37°C
6.4
-
in presence of 2-oxo-4-methylthiobutyric acid
additional information
pH OPTIMUM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
7.4 - 8.5
7.5 - 8
8
-
assay at
8.6
Monieza expansa
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-
8.6 - 8.8
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-
pH RANGE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
5.5 - 9.5
-
-
5.5 - 8
-
-
7.4 - 8.5
-
-
7.5 - 9.5
-
50% of optimal activity at 7.5 and 9.5
TEMPERATURE OPTIMUM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
SOURCE TISSUE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
SOURCE
-
S1, S2 and S3 region
Manually annotated by BRENDA team
MOLECULAR WEIGHT
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
47400
-
2 * 47400, SDS-PAGE
47700
-
x * 47700, MALDI-TOF
50000
-
x * 50000, x * 70000, SDS-PAGE
55000
-
2 * 55000, SDS-PAGE
72000
Monieza expansa
-
gel filtration
88000
-
gel filtration
93000
-
enzyme from rat kidney mitochondrion, most of the activity is present in the low-molecular weight fraction, gel filtration
100000
150000
-
FPLC gel filtration
200000
-
enzyme from rat kidney mitochondrion, some activity is present in the high-molecular weight fraction, gel filtration
330000
SUBUNITS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
homodimer
-
x-ray crystallography
monomer
Monieza expansa
-
1 * 65000-70000, SDS-PAGE
oligomer
-
x * 50000, x * 70000, SDS-PAGE
Crystallization/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
hanging drop vapour diffusion method, with 2 M ammonium sulfate and 0.1 M Tris at pH 8.5
-
pH STABILITY
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
3.2
-
70% loss of activity after 20 h
34543
4.3
-
20% loss of activity after 20 h
34543
5.3 - 8.9
-
95% of activity retained after 20 h
34543
TEMPERATURE STABILITY
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
55
-
98% activity lost after 5 min
60
-
complete loss of activity after 2 min
67
Monieza expansa
-
5 min, complete loss of activity
70
-
50% loss of activity after 10 min
100
-
no activity after 10 min
GENERAL STABILITY
ORGANISM
UNIPROT
LITERATURE
pyridoxal 5'-phosphate stabilizes
STORAGE STABILITY
ORGANISM
UNIPROT
LITERATURE
-20°C, 10 days, no loss of activity
-
-20°C, 3 months, no loss of activity
-
-20°C, 50 mM Tris-HCl, pH 8.0, 2 years, no significant decrease in activity
-
-20°C, 7 months, no loss of activity
-
-20°C, partially purified enzyme, 4 weeks, no loss of activity
Monieza expansa
-
4°C, partially purified enzyme ,1 week, 41% loss of activity
Monieza expansa
-
Cloned/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
expressed in a baculovirus/insect cell protein expression system
-
overexpression of cysteine-S-conjugate beta-lyase gene from Escherichia coli in a commercial wine yeast strain
-
APPLICATION
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
food industry
-
transformed wine yeast strain has a 10fold higher activity of cysteine-S-conjugate beta-lyase
medicine