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Information on EC 3.1.1.25 - 1,4-lactonase
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3.1.1.25 1,4-lactonaseIUBMB Comments
The enzyme is specific for 1,4-lactones with 4-8 carbon atoms. It does not hydrolyse simple aliphatic esters, acetylcholine, sugar lactones or substituted aliphatic lactones, e.g. 3-hydroxy-4-butyrolactone; requires Ca2+.
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Word Map
- 3.1.1.25
-
quorum
- homoserine
-
n-acyl
-
quorum-sensing
- solfataricus
-
ahl-degrading
-
n-acylhomoserine
-
quorum-quenching
-
phosphotriesterase-like
- pectobacterium
- carotovorum
- phosphotriesterase
- metallo-beta-lactamase
-
hxhxdh
-
c6-hsl
-
bioscavengers
-
ahl-mediated
-
acyl-homoserine
- ahl-lactonase
- synthesis
- medicine
The enzyme appears in viruses and cellular organisms
Synonyms
ahl lactonase, ssopox, vmolac, levo-lactonase, vmut_2255, 
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SYNONYM 
ORGANISM
UNIPROT
COMMENTARY 
LITERATURE
AHL lactonase
gamma-lactonase
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lactonase
lactonase, gamma
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levo-lactonase
Saci_2140
SacPox
SisLac
SSO2522
SsoPox
VmoLac
VMUT_2255
SisLac
the enzyme also shows activity of aryldialkylphosphatase (EC 3.1.8.1) and arylesterase (EC 3.1.1.2)
SisLac
the enzyme also shows activity of aryldialkylphosphatase (EC 3.1.8.1) and arylesterase (EC 3.1.1.2)
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REACTION
REACTION DIAGRAM
COMMENTARY
ORGANISM
UNIPROT
LITERATURE
a 1,4-lactone + H2O = a 4-hydroxyacid
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a 1,4-lactone + H2O = a 4-hydroxyacid
upon substrate binding, the zinc-bridging hydroxide anion is effectively protected from re-protonation by the plug-like function of the acyl tails whereupon the ring-opening reaction can proceed. Subsequent protonation of the product's alkoxide group can then be accomplished by the intramolecular proton transfer from the intermediate state's carboxylic acid group where the resulting carboxylate group better accommodates the still-neighboring zinc ion
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REACTION TYPE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
hydrolysis of carboxylic ester
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PATHWAY SOURCE
PATHWAYS
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SYSTEMATIC NAME
IUBMB Comments
1,4-lactone hydroxyacylhydrolase
The enzyme is specific for 1,4-lactones with 4-8 carbon atoms. It does not hydrolyse simple aliphatic esters, acetylcholine, sugar lactones or substituted aliphatic lactones, e.g. 3-hydroxy-4-butyrolactone; requires Ca2+.
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CAS REGISTRY NUMBER
COMMENTARY
37278-38-9
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SUBSTRATE
PRODUCT
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate)
(Substrate)
LITERATURE
(Substrate)
(Substrate)
COMMENTARY
(Product)
(Product)
LITERATURE
(Product)
(Product)
Reversibility
r=reversible
ir=irreversible
?=not specified
r=reversible
ir=irreversible
?=not specified
(2S,4RS)-2-hydroxy-4-butyrolactone + H2O
(S)-2-hydroxy-4-phenylbutyrate
-
-
-
-
?
(R)-alpha-hydroxy-gamma-butyrolactone + H2O
(R)-2-hydroxybutyric acid
enzyme variant Q192: 0.88% of the activity with phenyl acetate (cf. EC 3.1.1.2), enzyme variant R192: 3.95% of the activity with phenyl acetate (cf. EC 3.1.1.2)
-
-
?
(R)-dihydro-5-(hydroxymethyl)-2(3H)-furanone + H2O
?
enzyme variant Q192: 1.23% of the activity with phenyl acetate (cf. EC 3.1.1.2), enzyme variant R192: 3.29% of the activity with phenyl acetate (cf. EC 3.1.1.2)
-
-
?
(S)-alpha-hydroxy-gamma-butyrolactone + H2O
(S)-2-hydroxybutyric acid
enzyme variant Q192: 8.14% of the activity with phenyl acetate (cf. EC 3.1.1.2), enzyme variant R192: 19.6% of the activity with phenyl acetate (cf. EC 3.1.1.2)
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-
?
(S)-beta-hydroxy-gamma-butyrolactone + H2O
(S)-3-hydroxybutyric acid
enzyme variant Q192: 0.6% of the activity with phenyl acetate (cf. EC 3.1.1.2), enzyme variant R192: 0.76% of the activity with phenyl acetate (cf. EC 3.1.1.2)
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-
?
(S)-dihydro-5-(hydroxymethyl)-2(3H)-furanone + H2O
?
enzyme variant Q192: 0.78% of the activity with phenyl acetate (cf. EC 3.1.1.2), enzyme variant R192: 1.12% of the activity with phenyl acetate (cf. EC 3.1.1.2)
-
-
?
2-bromobutyrolactone + H2O
?
less than 1% activity compared to DL-pantoyl lactone
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-
?
2-hydroxybutyrolactone + H2O
?
2450% activity compared to DL-pantoyl lactone
-
-
?
3-oxo-octanoyl-L-homoserine lactone + H2O
N-(3-oxooctanoyl)-L-homoserine
-
-
-
?
4-(1-propenyloxymethyl)-1,3-dioxolan-2-one + H2O
?
enzyme variant Q192: 2.23% of the activity with phenyl acetate (cf. EC 3.1.1.2), enzyme variant R192: 2.52% of the activity with phenyl acetate (cf. EC 3.1.1.2)
-
-
?
4-butyrolactone + H2O
?
less than 1% activity compared to DL-pantoyl lactone
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-
?
4-phenyl-2-hydroxyl-4-butyrolactone + H2O
?
22% activity compared to DL-pantoyl lactone
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-
?
5-(thioethyl)butyrolactone + H2O
?
the lactonase and the esterase activity of PON1 is mediated by the His115-His134 dyad
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-
?
5-butyl-4-methyldihydro-2(3H)-furanone + H2O
4-hydroxy-3-methyl-octanoate
i.e. whiskey lactone
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-
?
5-hydroxy-(6E,8Z,11Z,14Z)-eicosatetraenoic acid 1,5-lactone + H2O
5-hydroxy-(6E,8Z,11Z,14Z)-eicosatetraenoic acid
-
-
-
?
5-hydroxy-6E,8Z,11Z,14Z-eicosatetraenoic acid 1,5-lactone + H2O
5-hydroxy-6E,8Z,11Z,14Z-eicosatetraenoic acid
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-
-
?
5-thiobutyl butyrolactone + H2O
4-(butylsulfanyl)-4-hydroxybutanoic acid
-
-
-
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?
7-O-diethyl phosphoryl 3-cyano 4-methyl 7-hydroxycoumarin + H2O
?
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-
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?
7-O-diethylphosphoryl-3-cyano-4-methyl-7-hydroxycoumarin + H2O
(2Z)-2-cyano-3-[4-[(diethoxyphosphoryl)oxy]-2-hydroxyphenyl]but-2-enoic acid
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-
-
-
?
7-oxo-N-(2-oxotetrahydrofuran-3-yl)nonanamide + H2O
3-hydroxy-2-[(7-oxononanoyl)amino]propanoic acid
9-oxo-N-(2-oxotetrahydrofuran-3-yl)undecanamide + H2O
3-hydroxy-2-[(9-oxoundecanoyl)amino]propanoate
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-
-
?
9-oxo-N-(2-oxotetrahydrofuran-3-yl)undecanamide + H2O
3-hydroxy-2-[(9-oxoundecanoyl)amino]propanoic acid
-
-
-
?
alpha-angelicalactone + H2O
4-hydroxy-pent-3-enoic acid
-
-
-
?
alpha-angelicalactone + H2O
4-hydroxypent-3-enoic acid
-
-
-
?
alpha-angelicalactone + H2O
?
enzyme variant Q192: 19.9% of the activity with phenyl acetate (cf. EC 3.1.1.2), enzyme variant R192: 14.8% of the activity with phenyl acetate (cf. EC 3.1.1.2)
-
-
?
alpha-bromo-gamma-butyrolactone + H2O
2-bromobutyric acid
enzyme variant Q192: 47.2% of the activity with phenyl acetate (cf. EC 3.1.1.2), enzyme variant R192: 40.8% of the activity with phenyl acetate (cf. EC 3.1.1.2)
-
-
?
alpha-hydroxy-beta,beta-dimethyl-gamma-butyrolactone + H2O
2,4-dihydroxy-3,3-dimethylbutanoate
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-
-
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?
alpha-hydroxy-gamma-butyrolactone + H2O
2,4-dihydroxybutanoate
-
-
-
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?
beta-hydroxy-gamma-butyrolactone + H2O
3,4-dihydroxybutanoate
-
-
-
-
?
canrenone + H2O
?
not hydrolyzed by PON1 (P27169 (UniProt)) and PON2 (Q15165 (UniProt))
-
-
?
delta-tetradecanolactone + H2O
5-hydroxytetradecanoic acid
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-
-
?
delta-undecanolactone + H2O
5-hydroxyundecanoic acid
-
-
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?
DL-3-oxo-hexanoyl-homoserine lactone + H2O
DL-3-oxo-hexanoyl-homoserine
-
-
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?
DL-3-oxo-hexanoylhomoserine lactone + H2O
DL-3-oxo-hexanoylhomoserine
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-
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?
DL-dodecanoyl-homoserine lactone + H2O
DL-dodecanoyl-homoserine
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-
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?
DL-dodecanoylhomoserine lactone + H2O
DL-dodecanoylhomoserine
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-
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?
DL-heptanoyl-homoserine lactone + H2O
DL-heptanoyl-homoserine
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-
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?
DL-heptanoylhomoserine lactone + H2O
DL-heptanoylhomoserine
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-
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?
DL-tetradecanoyl-homoserine lactone + H2O
DL-tetradecanoyl-homoserine
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-
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?
DL-tetradecanoylhomoserine lactone + H2O
DL-tetradecanoyl-homoserine
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-
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?
DL-tetradecanoylhomoserine lactone + H2O
DL-tetradecanoylhomoserine
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-
-
?
epsilon-caprolactone + H2O
6-hydroxyhexanoic acid
enzyme variant Q192: 14.8% of the activity with phenyl acetate (cf. EC 3.1.1.2), enzyme variant R192: 25.7% of the activity with phenyl acetate (cf. EC 3.1.1.2)
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?
ethyl acetate + H2O
?
less than 1% activity compared to DL-pantoyl lactone
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?
gamma-(R)-caprolactone + H2O
4-hydroxyhexanoate
slight preference but not an exclusive specificity for the (R)-enantiomers of capro- and valerolactone
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?
gamma-(R)-valerolactone + H2O
4-hydroxypentanoate
slight preference but not an exclusive specificity for the (R)-enantiomers of capro- and valerolactone
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?
gamma-(S)-caprolactone + H2O
4-hydroxyhexanoate
slight preference but not an exclusive specificity for the (R)-enantiomers of capro- and valerolactone
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?
gamma-(S)-valerolactone + H2O
4-hydroxypentanoate
slight preference but not an exclusive specificity for the (R)-enantiomers of capro- and valerolactone
-
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?
gamma-phenyl-gamma-butyrolactone + H2O
4-hydroxy-4-phenyl-butanoic acid
-
-
-
?
gamma-phenyl-gamma-butyrolactone + H2O
4-hydroxy-4-phenylbutanoic acid
-
-
-
?
gamma-undecanolactone + H2O
4-hydroxyundecanoic acid
-
-
-
?
methyl 2-chloroacetate + H2O
?
11.6% activity compared to DL-pantoyl lactone
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-
?
methyl 2-chloropropanoate + H2O
?
2.3% activity compared to DL-pantoyl lactone
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-
?
methyl lactate + H2O
?
less than 1% activity compared to DL-pantoyl lactone
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-
?
methyl mandelate + H2O
?
less than 1% activity compared to DL-pantoyl lactone
-
-
?
N-(2-oxotetrahydrofuran-3-yl)nonanamide + H2O
3-hydroxy-2-(nonanoylamino)propanoate
-
-
-
?
N-(2-oxotetrahydrofuran-3-yl)pentanamide + H2O
3-hydroxy-2-(pentanoylamino)propanoate
-
-
-
?
N-(2-oxotetrahydrofuran-3-yl)pentanamide + H2O
3-hydroxy-2-(pentanoylamino)propanoic acid
-
-
-
?
N-(3-oxobutanoyl)-DL-homoserine lactone + H2O
N-(3-oxobutanoyl)-DL-homoserine
-
-
-
?
N-(3-oxodecanoyl)-DL-homoserine lactone + H2O
N-(3-oxodecanoyl)-DL-homoserine
-
-
-
?
N-(3-oxododecanoyl)-DL-homoserine lactone + H2O
N-(3-oxododecanoyl)-DL-homoserine
-
-
-
?
N-(3-oxododecanoyl)-L-homoserine lactone + H2O
N-(3-oxododecanoyl)-L-homoserine
-
-
-
?
N-(3-oxohexanoyl)homoserine lactone + H2O
N-(3-oxohexanoyl)homoserine
-
-
-
?
N-(3-oxooctanoyl)-DL-homoserine lactone + H2O
N-(3-oxooctanoyl)-DL-homoserine
-
-
-
?
N-(3-oxooctanoyl)homoserine lactone + H2O
N-(3-oxooctanoyl)homoserine
-
-
-
?
N-butanoyl-DL-homoserine lactone + H2O
N-butanoyl-L-homoserine
-
-
-
?
N-butanoylhomoserine lactone + H2O
N-butanoylhomoserine
-
-
-
?
N-dodecanoyl-DL-homoserine lactone + H2O
N-dodecanoyl-DL-homoserine
-
-
-
?
N-dodecanoylhomoserine lactone + H2O
N-dodecanoylhomoserine
-
-
-
?
N-hexanoylhomoserine lactone + H2O
N-hexanoylhomoserine
-
-
-
?
N-octanoyl-DL-homoserine lactone + H2O
octanoyl-homoserine
-
-
-
?
N-octanoylhomoserine lactone + H2O
N-octanoylhomoserine
-
-
-
?
octanoyl-L-homoserine lactone + H2O
N-octanoyl-L-homoserine
-
-
-
?
propylene carbonate + H2O
?
enzyme variant Q192: 5.02% of the activity with phenyl acetate (cf. EC 3.1.1.2), enzyme variant R192: 8.8% of the activity with phenyl acetate (cf. EC 3.1.1.2)
-
-
?
undecano-gamma-lactone + H2O
4-hydroxyundecanoic acid
enzyme variant Q192: 11.8% of the activity with phenyl acetate (cf. EC 3.1.1.2), enzyme variant R192: 12.7% of the activity with phenyl acetate (cf. EC 3.1.1.2)
-
-
?
(1R,5S)-oxabicyclooctenone + H2O
?
enzyme variant Q192: 0.82% of the activity with phenyl acetate (cf. EC 3.1.1.2), enzyme variant R192: 0.75% of the activity with phenyl acetate (cf. EC 3.1.1.2)
-
-
?
(1S,5R)-oxabicyclooctenone + H2O
?
enzyme variant Q192: 1.67% of the activity with phenyl acetate (cf. EC 3.1.1.2), enzyme variant R192: 2.92% of the activity with phenyl acetate (cf. EC 3.1.1.2)
-
-
?
2-coumaranone + H2O
(2-hydroxyphenyl)acetic acid
enzyme variant Q192: 18.3% of the activity with phenyl acetate (cf. EC 3.1.1.2), enzyme variant R192: 13.5% of the activity with phenyl acetate (cf. EC 3.1.1.2)
-
-
?
2-coumaranone + H2O
?
-
25% of activity compared to L-pantoyl lactone
-
?
2-coumaranone + H2O
?
-
25% of activity compared to L-pantoyl lactone
-
?
3,4-dihydrocoumarin + H2O
?
-
23% of activity compared to L-pantoyl lactone
-
?
3,4-dihydrocoumarin + H2O
?
-
23% of activity compared to L-pantoyl lactone
-
?
3-oxo-decanoyl-L-homoserine lactone + H2O
N-(3-oxodecanoyl)-L-homoserine
-
-
-
?
3-oxo-decanoyl-L-homoserine lactone + H2O
N-(3-oxodecanoyl)-L-homoserine
-
-
-
?
5-(thiobutyl)butyrolactone + H2O
?
the lactonase and the esterase activity of PON1 is mediated by the His115-His134
-
-
?
5-(thiobutyl)butyrolactone + H2O
?
the lactonase and the esterase activity of PON1 is mediated by the His115-His134 dyad
-
-
?
7-oxo-N-(2-oxotetrahydrofuran-3-yl)nonanamide + H2O
3-hydroxy-2-[(7-oxononanoyl)amino]propanoic acid
-
-
-
?
7-oxo-N-(2-oxotetrahydrofuran-3-yl)nonanamide + H2O
3-hydroxy-2-[(7-oxononanoyl)amino]propanoic acid
-
-
-
?
beta-hydroxybutyrolactone + H2O
?
enzyme variant Q192: 3.83% of the activity with phenyl acetate (cf. EC 3.1.1.2), enzyme variant R192: 7.53% of the activity with phenyl acetate (cf. EC 3.1.1.2)
-
-
?
delta-decanolactone + H2O
5-hydroxydecanoic acid
enzyme variant Q192: 9.65% of the activity with phenyl acetate (cf. EC 3.1.1.2), enzyme variant R192: 12.8% of the activity with phenyl acetate (cf. EC 3.1.1.2)
-
-
?