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4.4.1.4: alliin lyase

This is an abbreviated version!
For detailed information about alliin lyase, go to the full flat file.

Word Map on EC 4.4.1.4

Reaction

an S-alkyl-L-cysteine S-oxide
=
an alkyl sulfenate
+
2-aminoacrylate

Synonyms

alkylcysteine sulfoxide lyase, alkylsulphenate lyase, ALL1, alliin lyase, alliin-lyase, alliinase, alliinase I, alliinase II, allinase, C-S lyase, C-S-lyase, cys sulfoxide lyase, cysteine sulfoxide lyase, Cysteine sulphoxide lyase, L-(+)-S-alk(en)ylcysteine sulfoxide lyase, L-cysteine sulfoxide lyase, lyase, alliin, More, P-19486 alliinase, S-alkyl(en)yl-L-cysteine lyase, S-alkylcysteine sulfoxide lyase

ECTree

     4 Lyases
         4.4 Carbon-sulfur lyases
             4.4.1 Carbon-sulfur lyases (only sub-subclass identified to date)
                4.4.1.4 alliin lyase

Substrates Products

Substrates Products on EC 4.4.1.4 - alliin lyase

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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
(+)-(S)-allyl-L-cysteine sulfoxide
2-propenyl 2-propenethiosulfinate + pyruvate + NH3
show the reaction diagram
-
-
i.e. allicin
-
?
(+)-alliin
allicin + pyruvic acid + NH3
show the reaction diagram
(+)-alliin + H2O
allicin + pyruvate + NH3
show the reaction diagram
-
-
-
?
(+)-methiin + H2O
methanesulfenic acid + pyruvate + NH3
show the reaction diagram
-
-
-
?
(+)-propiin + H2O
propane-1-sulfenic acid + pyruvate + NH3
show the reaction diagram
-
-
-
?
(+)-S-(2-propenyl)-L-cysteine sulfoxide
2-propene-thioic acid + pyruvate + ammonia
show the reaction diagram
(+)-S-propyl-L-cysteine sulfoxide
propane-1-sulfenic acid + pyruvate + NH3
show the reaction diagram
(+-)-alliin + H2O
allicin + pyruvate + NH3
show the reaction diagram
-
-
-
?
(+-)-ethiin + H2O
ethanesulfenic acid + pyruvate + NH3
show the reaction diagram
-
-
-
?
(+-)-methiin + H2O
methanesulfenic acid + pyruvate + NH3
show the reaction diagram
-
-
-
?
(+-)-propiin + H2O
propane-1-sulfenic acid + pyruvate + NH3
show the reaction diagram
-
-
-
?
(+/-)-(1-methyl)-L-cysteine sulfoxide
methanesulfenic acid + pyruvate + NH3
show the reaction diagram
(+/-)-(butyl)-L-cysteine sulfoxide
butane-1-sulfenic acid + pyruvate + NH3
show the reaction diagram
(+/-)-(propyl)-L-cysteine sulfoxide
propyl-1-sulfenic acid + pyruvate + NH3
show the reaction diagram
(+/-)-alliin
allicin + pyruvic acid + NH3
show the reaction diagram
(+/-)-S-methyl-L-cysteine sulfoxide
?
show the reaction diagram
-
high activity
-
-
?
(-)-(2-propenyl)-L-cysteine sulfoxide
2-propene-thioic acid + pyruvate + ammonia
show the reaction diagram
(-)-alliin
allicin + pyruvic acid + NH3
show the reaction diagram
(-)cystathionine
?
show the reaction diagram
-
3% of the activity with desglutamyl-lentinic acid
-
-
?
(2R)-2-amino-3-(1-phenylethylsulfinyl)propanoic acid
(1-phenylethyl)sulfanol + pyruvate + NH4+
show the reaction diagram
-
-
The sulfenic acid condenses with loss of water to form thiosulfinates. The alpha-aminoacrylic acid formed initially subsequently breaks down into pyruvate and ammonia
-
?
(2R)-2-amino-3-(2-methylbenzylsulfinyl)propanoic acid
(2-methylbenzyl)sulfanol + pyruvate + NH4+
show the reaction diagram
-
-
The sulfenic acid condenses with loss of water to form thiosulfinates. The alpha-aminoacrylic acid formed initially subsequently breaks down into pyruvate and ammonia
-
?
(2R)-2-amino-3-(4-chlorobenzylsulfinyl)propanoic acid
(4-chlorobenzyl)sulfanol + pyruvate + NH4+
show the reaction diagram
-
-
The sulfenic acid condenses with loss of water to form thiosulfinates. The alpha-aminoacrylic acid formed initially subsequently breaks down into pyruvate and ammonia
-
?
(2R)-2-amino-3-(4-methylbenzylsulfinyl)propanoic acid
(4-methylbenzyl)sulfanol + pyruvate + NH4+
show the reaction diagram
-
-
The sulfenic acid condenses with loss of water to form thiosulfinates. The alpha-aminoacrylic acid formed initially subsequently breaks down into pyruvate and ammonia
-
?
(2R)-2-amino-3-(ethylsulfinyl)propanoic acid
(2R)-2-amino-3-(ethylsulfinyl)propanoic acid + pyruvate + NH4+
show the reaction diagram
-
-
The sulfenic acid condenses with loss of water to form thiosulfinates. The alpha-aminoacrylic acid formed initially subsequently breaks down into pyruvate and ammonia
-
?
(2R)-2-amino-3-(phenethylsulfinyl)propanoic acid
phenethylsulfanol + pyruvate + NH4+
show the reaction diagram
-
-
The sulfenic acid condenses with loss of water to form thiosulfinates. The alpha-aminoacrylic acid formed initially subsequently breaks down into pyruvate and ammonia
-
?
(2R)-2-amino-3-(phenylsulfinyl)propanoic acid
phenylsulfanol + pyruvate + NH4+
show the reaction diagram
-
-
The sulfenic acid condenses with loss of water to form thiosulfinates. The alpha-aminoacrylic acid formed initially subsequently breaks down into pyruvate and ammonia
-
?
(R)-S-(2-pyridyl)cysteine N-oxide
2-sulfanylpyridine N-oxide + 2-aminoacrylate
show the reaction diagram
-
-
2-sulfanylpyridine N-oxide can spontaneously rearrange into tautomeric and more stable N-hydroxypyridine-(1H)-thione, which can be transformed to 2-(methyldithio)pyridine N-oxide, 2-[(methylthio)methyldithio]pyridine N-oxide, di(2-pyridyl) disulfide N-oxide, and di(2-pyridyl) disulfide N,N'-dioxide
-
?
(S)-(2-pyrrolyl)cysteine
2-pyrrolesulfenic acid + 2-aminoacrylate
show the reaction diagram
(S)-(2-pyrrolyl)cysteine S-oxide
2-pyrrolesulfenic acid + 2-aminoacrylate
show the reaction diagram
(S)-(3-pyrrolyl)cysteine S-oxide
3-pyrrolesulfenic acid + 2-aminoacrylate
show the reaction diagram
2 alliin + H2O
allicin + 2 pyruvate + 2 NH3
show the reaction diagram
2 S-allyl-Cys sulfoxide + H2O
allicin + 2 pyruvate + 2 NH3
show the reaction diagram
-
-
-
-
?
2 S-allyl-L-Cys sulfoxide + H2O
allicin + 2 pyruvate + 2 NH3
show the reaction diagram
-
-
-
-
?
2 S-ethyl-L-Cys sulfoxide + H2O
ethyl ethanethiosulfinate + 2 pyruvate + 2 NH3
show the reaction diagram
2-hydroxyethiin
(2-hydroxyethyl)sulfanol + pyruvate + NH4+
show the reaction diagram
-
-
The sulfenic acid condenses with loss of water to form thiosulfinates. The alpha-aminoacrylic acid formed initially subsequently breaks down into pyruvate and ammonia
-
?
4-mercaptopyridine
?
show the reaction diagram
-
-
-
-
?
alliin
2-propene-thioic acid + pyruvate + NH4+
show the reaction diagram
alliin
allylsulfenic acid + pyruvate + NH3
show the reaction diagram
alliin + H2O
allicin + pyruvate + NH3
show the reaction diagram
beta-chloro-L-Ala
?
show the reaction diagram
-
95% of the activity with desglutamyl-lentinic acid
-
-
?
butiin
butane-1-sulfenic acid + pyruvate + NH3
show the reaction diagram
cystine
?
show the reaction diagram
-
-
-
-
?
desglutamyl-lentinic acid
?
show the reaction diagram
-
-
-
-
?
djenkolic acid
?
show the reaction diagram
-
-
-
-
?
ethiin
ethanesulfenic acid + pyruvate + NH3
show the reaction diagram
ethiin + H2O
ethanesulfenic acid + pyruvate + NH3
show the reaction diagram
-
-
-
?
isoalliin
? + pyruvate + NH4+
show the reaction diagram
-
-
The sulfenic acid condenses with loss of water to form thiosulfinates. The alpha-aminoacrylic acid formed initially subsequently breaks down into pyruvate and ammonia
-
?
L-(+)-alliin
2-propene-thioic acid + pyruvate + NH4+
show the reaction diagram
L-(+)-isoalliin
?
show the reaction diagram
L-(+)-S-(2-pyridyl)-cysteine sulfoxide + H2O
?
show the reaction diagram
-
the amount of this cysteine sulfoxide, related to the fresh weight of bulbs, is between 0.13 and 0.44%
-
-
?
L-(-)-alliin
2-propene-thioic acid + pyruvate + NH4+
show the reaction diagram
L-Cys
?
show the reaction diagram
-
0.4% of the activity with desglutamyl-lentinic acid
-
-
?
L-Cys sulfinic acid
?
show the reaction diagram
-
0.5% of the activity with desglutamyl-lentinic acid
-
-
?
L-cysteine
?
show the reaction diagram
L-cystine
?
show the reaction diagram
L-cystine
pyruvate + NH4+ + S2- + L-cysteine
show the reaction diagram
-
cystine lyase activity of the enzyme alliinase
-
-
?
methiin
methanesulfenic acid + 2-aminoacrylate
show the reaction diagram
methiin + H2O
?
show the reaction diagram
-
-
-
-
?
methiin + H2O
methanesulfenic acid + pyruvate + NH3
show the reaction diagram
petiveriin
benzylsulfanol + pyruvate + NH4+
show the reaction diagram
propiin
propane-1-sulfenic acid + pyruvate + NH3
show the reaction diagram
propiin
propylsulfanol + pyruvate + NH4+
show the reaction diagram
-
-
The sulfenic acid condenses with loss of water to form thiosulfinates. The alpha-aminoacrylic acid formed initially subsequently breaks down into pyruvate and ammonia
-
?
S-(+)-allyl-L-cysteine sulfoxide + H2O
allyl 2-propenethiosulphinate
show the reaction diagram
-
-
-
-
?
S-(1-butenyl)-L-cysteine sulfoxide
?
show the reaction diagram
S-(2-chloro-4-nitrophenyl)-L-Cys
?
show the reaction diagram
-
-
-
-
?
S-(2-chloro-6-nitrophenyl)-L-Cys
?
show the reaction diagram
-
-
-
-
?
S-(2-hydroxyethyl)-L-cysteine sulfoxide
? + pyruvate + NH3
show the reaction diagram
-
-
-
-
?
S-(methylthiomethyl)cysteine 4-oxide
(methylthio)methane-sulfenic acid + 2-aminoacrylate
show the reaction diagram
-
i.e. marasmin
-
-
?
S-allyl-L-Cys
?
show the reaction diagram
-
4% of the activity with desglutamyl-lentinic acid
-
-
?
S-allyl-L-Cys sulfoxide + H2O
2-propenesulfenic acid + pyruvate + NH3
show the reaction diagram
-
-
-
-
?
S-allyl-L-cysteine
?
show the reaction diagram
-
high activity
-
-
?
S-allyl-L-cysteine sulfoxide + H2O
2-propene-thioic acid + pyruvate + NH4+ + H+
show the reaction diagram
S-benzyl-L-cysteine sulfoxide
phenylmethanesulfenic acid + pyruvate + NH3
show the reaction diagram
-
-
-
-
?
S-butyl-L-Cys sulfoxide
?
show the reaction diagram
-
-
-
-
?
S-butyl-L-cysteine + H2O
butanethiol + NH3 + 2-oxopropanoate
show the reaction diagram
-
-
-
?
S-ethyl-cysteine sulfoxide
diethyldisulfide-S-monoxide + pyruvate + NH4+
show the reaction diagram
-
-
-
-
?
S-ethyl-L-Cys
?
show the reaction diagram
S-ethyl-L-Cys sulfoxide + H2O
ethanesulfenic acid + pyruvate + NH3
show the reaction diagram
-
-
-
-
?
S-ethyl-L-Cys sulfoxide + H2O
ethylsulfenic acid + pyruvate + NH3
show the reaction diagram
S-ethyl-L-cysteine
?
show the reaction diagram
S-ethyl-L-cysteine + H2O
ethanethiol + NH3 + 2-oxopropanoate
show the reaction diagram
-
-
-
?
S-ethyl-L-cysteine sulfoxide + H2O
ethyl 2-propenethiosulfinate
show the reaction diagram
-
-
-
-
?
S-methyl-cysteine sulfoxide
dimethyldisulfide-S-monoxide + pyruvate + NH4+
show the reaction diagram
-
-
-
-
?
S-methyl-L-Cys
?
show the reaction diagram
-
0.9% of the activity with desglutamyl-lentinic acid
-
-
?
S-methyl-L-Cys sulfone
?
show the reaction diagram
-
6% of the activity with desglutamyl-lentinic acid
-
-
?
S-methyl-L-Cys sulfoxide
?
show the reaction diagram
S-methyl-L-Cys sulfoxide
methanesulfenic acid + pyruvate + NH3
show the reaction diagram
-
-
-
-
?
S-methyl-L-cysteine
?
show the reaction diagram
S-methyl-L-cysteine + H2O
methanethiol + NH3 + 2-oxopropanoate
show the reaction diagram
-
-
-
?
S-methyl-L-cysteine sulfoxide
pyruvate + ?
show the reaction diagram
-
-
-
?
S-phenyl-L-Cys sulfoxide
?
show the reaction diagram
-
-
-
-
?
S-propenyl-L-Cys sulfoxide
?
show the reaction diagram
-
-
-
-
?
S-propyl-cysteine sulfoxide
dipropyldisulfide-S-monoxide + pyruvate + NH4+
show the reaction diagram
-
-
-
-
?
S-propyl-L-Cys
?
show the reaction diagram
S-propyl-L-Cys sulfoxide
?
show the reaction diagram
S-propyl-L-Cys sulfoxide
propanesulfenic acid + pyruvate + NH4+
show the reaction diagram
-
-
-
-
?
S-propyl-L-cysteine + H2O
propanethiol + NH3 + 2-oxopropanoate
show the reaction diagram
-
-
-
?
trans-(+)-S-(1-propenyl)-L-cysteine sulfoxide
?
show the reaction diagram
trans-(+)-S-propenyl-L-Cys sulfoxide
?
show the reaction diagram
-
-
-
-
?
additional information
?
-