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

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EC NUMBER
COMMENTARY hide
4.4.1.13
-
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RECOMMENDED NAME
GeneOntology No.
cysteine-S-conjugate beta-lyase
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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)
-
-
-
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REACTION TYPE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
elimination
-
-
of H2S or RSH, C-S bond cleavage
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transamination
additional information
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PATHWAY
BRENDA Link
KEGG Link
MetaCyc Link
glutathione-mediated detoxification I
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-
glutathione-mediated detoxification II
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Selenocompound metabolism
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-
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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.
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CAS REGISTRY NUMBER
COMMENTARY hide
68652-57-3
-
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ORGANISM
COMMENTARY hide
LITERATURE
UNIPROT
SEQUENCE DB
SOURCE
-
-
-
Manually annotated by BRENDA team
-
-
-
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
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-
-
Manually annotated by BRENDA team
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-
-
Manually annotated by BRENDA team
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-
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Manually annotated by BRENDA team
strain DSM 20701
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-
Manually annotated by BRENDA team
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-
-
Manually annotated by BRENDA team
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GENERAL INFORMATION
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
malfunction
metabolism
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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
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-
-
-
?
S-methylmercapto-L-cysteine + H2O
NH3 + pyruvate + methanethiol
show the reaction diagram
-
-
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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
-
-
-
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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
?
-
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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
?
-
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COFACTOR
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
pyridoxal 5'-phosphate
additional information
-
no cofactor requirement
-
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METALS and IONS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
additional information
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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
-
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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
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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
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-
2.6
beta-chloroalanine
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-
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
-
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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
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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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-
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pH RANGE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
5.5 - 9.5
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-
5.5 - 8
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-
7.4 - 8.5
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-
7.5 - 9.5
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50% of optimal activity at 7.5 and 9.5
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TEMPERATURE OPTIMUM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
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SOURCE TISSUE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
SOURCE
-
S1, S2 and S3 region
Manually annotated by BRENDA team
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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
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SUBUNITS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
homodimer
-
x-ray crystallography
monomer
Monieza expansa
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1 * 65000-70000, SDS-PAGE
oligomer
-
x * 50000, x * 70000, SDS-PAGE
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Crystallization/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
hanging drop vapour diffusion method, with 2 M ammonium sulfate and 0.1 M Tris at pH 8.5
-
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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
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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
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GENERAL STABILITY
ORGANISM
UNIPROT
LITERATURE
pyridoxal 5'-phosphate stabilizes
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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
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4°C, partially purified enzyme ,1 week, 41% loss of activity
Monieza expansa
-
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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
-
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APPLICATION
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
food industry
-
transformed wine yeast strain has a 10fold higher activity of cysteine-S-conjugate beta-lyase
medicine
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LINKS TO OTHER DATABASES (specific for EC-Number 4.4.1.13)
ExplorEnz
ExPASy
KEGG
MetaCyc
SABIO-RK
NCBI: PubMed, Protein, Nucleotide, Structure, Genome, OMIM
IUBMB Enzyme Nomenclature
PROSITE Database of protein families and domains
InterPro (database of protein families, domains and functional sites)