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Information on EC 3.1.1.25 - 1,4-lactonase and Organism(s) Saccharolobus solfataricus and UniProt Accession Q97VT7

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EC Tree
     3 Hydrolases
         3.1 Acting on ester bonds
             3.1.1 Carboxylic-ester hydrolases
                3.1.1.25 1,4-lactonase
IUBMB 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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This record set is specific for:
Saccharolobus solfataricus
UNIPROT: Q97VT7
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Word Map
The taxonomic range for the selected organisms is: Saccharolobus solfataricus
The enzyme appears in selected viruses and cellular organisms
Synonyms
ahl lactonase, ssopox, vmolac, levo-lactonase, vmut_2255, more
SYNONYM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
gamma-lactonase
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-
-
-
lactonase, gamma
-
-
-
-
REACTION TYPE
ORGANISM
UNIPROT
COMMENTARY hide
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+.
CAS REGISTRY NUMBER
COMMENTARY hide
37278-38-9
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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
delta-dodecanolactone + H2O
5-hydroxydodecanoate
show the reaction diagram
-
-
-
?
delta-nonalactone + H2O
5-hydroxynonanoate
show the reaction diagram
-
-
-
?
delta-undecanolactone + H2O
5-hydroxyundecanoate
show the reaction diagram
-
-
-
?
dihydrocoumarin + H2O
3-(2-hydroxyphenyl)-propionic acid
show the reaction diagram
-
-
-
?
epsilon-caprolactone + H2O
?
show the reaction diagram
-
-
-
?
gamma-butyrolactone + H2O
4-hydroxybutanoate
show the reaction diagram
-
-
-
?
gamma-dodecanolactone + H2O
4-hydroxydodecanoate
show the reaction diagram
-
-
-
?
gamma-heptanolactone + H2O
4-hydroxyheptanoate
show the reaction diagram
-
-
-
?
gamma-nonalactone + H2O
4-hydroxynonanoate
show the reaction diagram
-
-
-
?
gamma-undecanolactone + H2O
4-hydroxyundecanoate
show the reaction diagram
-
-
-
?
N-(3-oxodecanoyl)-L-homoserine lactone + H2O
N-(3-oxodecanoyl)-L-homoserine
show the reaction diagram
N-(3-oxododecanoyl)-L-homoserine lactone + H2O
N-(3-oxododecanoyl)-L-homoserine
show the reaction diagram
-
-
-
?
N-(3-oxohexanoyl)-L-homoserine lactone + H2O
N-(3-oxohexanoyl)-L-homoserine
show the reaction diagram
-
-
-
?
N-(3-oxohexanoyl)homoserine lactone + H2O
N-(3-oxohexanoyl)homoserine
show the reaction diagram
-
-
-
?
N-(3-oxooctanoyl)-L-homoserine lactone + H2O
N-(3-oxooctanoyl)-L-homoserine
show the reaction diagram
-
-
-
?
N-(3-oxooctanoyl)homoserine lactone + H2O
N-(3-oxooctanoyl)homoserine
show the reaction diagram
-
-
-
?
N-butanoylhomoserine lactone + H2O
N-butanoylhomoserine
show the reaction diagram
-
-
-
?
N-dodecanoylhomoserine lactone + H2O
N-dodecanoylhomoserine
show the reaction diagram
-
-
-
?
N-hexanoylhomoserine lactone + H2O
N-hexanoylhomoserine
show the reaction diagram
-
-
-
?
N-octanoylhomoserine lactone + H2O
N-octanoylhomoserine
show the reaction diagram
-
-
-
?
paraoxon + H2O
diethylphosphate + 4-nitrophenol
show the reaction diagram
-
-
-
?
NATURAL SUBSTRATE
NATURAL PRODUCT
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate) hide
LITERATURE
(Substrate)
COMMENTARY
(Product) hide
LITERATURE
(Product)
REVERSIBILITY
r=reversible
ir=irreversible
?=not specified
N-(3-oxodecanoyl)-L-homoserine lactone + H2O
N-(3-oxodecanoyl)-L-homoserine
show the reaction diagram
the best, possibly natural, substrate of wild-type enzyme
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-
?
INHIBITOR
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
delta-undecanolactone
contrary to the wild-type enzyme and mutant enzyme W263F, the mutant enzymes W263M, W263L, W263I, W263V and W263T exhibit a substrate inhibition
KM VALUE [mM]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
1.678
delta-dodecanolactone
pH 8.3, 25°C, wild-type enzyme
0.359
delta-nonalactone
pH 8.3, 25°C, wild-type enzyme
0.057 - 0.219
delta-undecanolactone
1.376
dihydrocoumarin
pH 8.3, 25°C, wild-type enzyme
0.234
epsilon-caprolactone
pH 8.3, 25°C, wild-type enzyme
1.22
gamma-dodecanolactone
pH 8.3, 25°C, wild-type enzyme
0.166
gamma-heptanolactone
pH 8.3, 25°C, wild-type enzyme
2.943
gamma-nonalactone
pH 8.3, 25°C, wild-type enzyme
0.013 - 2.099
gamma-undecanolactone
0.143 - 1.605
N-(3-oxodecanoyl)-L-homoserine lactone
0.0178 - 0.456
N-(3-oxododecanoyl)-L-homoserine lactone
0.558
N-(3-oxohexanoyl)-L-homoserine lactone
pH 8.3, 25°C, wild-type enzyme
0.592
N-(3-oxohexanoyl)homoserine lactone
pH 8.3, 25°C, wild-type enzyme
0.123
N-(3-oxooctanoyl)-L-homoserine lactone
pH 8.3, 25°C, wild-type enzyme
0.256
N-(3-oxooctanoyl)homoserine lactone
pH 8.3, 25°C, wild-type enzyme
0.345
N-dodecanoylhomoserine lactone
pH 8.3, 25°C, wild-type enzyme
0.459
N-hexanoylhomoserine lactone
pH 8.3, 25°C, wild-type enzyme
0.145
N-octanoylhomoserine lactone
pH 8.3, 25°C, wild-type enzyme
0.7 - 24.2
paraoxon
TURNOVER NUMBER [1/s]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
15.32
delta-nonalactone
pH 8.3, 25°C, wild-type enzyme
7.38 - 93.3
delta-undecanolactone
7.32
dihydrocoumarin
pH 8.3, 25°C, wild-type enzyme
4.45
epsilon-caprolactone
pH 8.3, 25°C, wild-type enzyme
2.72
gamma-dodecanolactone
pH 8.3, 25°C, wild-type enzyme
2.92
gamma-heptanolactone
pH 8.3, 25°C, wild-type enzyme
5.54
gamma-nonalactone
pH 8.3, 25°C, wild-type enzyme
1.94 - 5.64
gamma-undecanolactone
0.107 - 4.52
N-(3-oxodecanoyl)-L-homoserine lactone
0.41 - 6.44
N-(3-oxododecanoyl)-L-homoserine lactone
0.083
N-(3-oxohexanoyl)-L-homoserine lactone
pH 8.3, 25°C, wild-type enzyme
0.041
N-(3-oxohexanoyl)homoserine lactone
pH 8.3, 25°C, wild-type enzyme
0.54
N-(3-oxooctanoyl)-L-homoserine lactone
pH 8.3, 25°C, wild-type enzyme
0.42
N-(3-oxooctanoyl)homoserine lactone
pH 8.3, 25°C, wild-type enzyme
1.7
N-dodecanoylhomoserine lactone
pH 8.3, 25°C, wild-type enzyme
0.36
N-hexanoylhomoserine lactone
pH 8.3, 25°C, wild-type enzyme
1
N-octanoylhomoserine lactone
pH 8.3, 25°C, wild-type enzyme
6.82 - 12.6
paraoxon
kcat/KM VALUE [1/mMs-1]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
7.54
delta-dodecanolactone
pH 8.3, 25°C, wild-type enzyme
42.7
delta-nonalactone
pH 8.3, 25°C, wild-type enzyme
78.6 - 792
delta-undecanolactone
5.32
dihydrocoumarin
pH 8.3, 25°C, wild-type enzyme
19
epsilon-caprolactone
pH 8.3, 25°C, wild-type enzyme
1.2
gamma-butyrolactone
pH 8.3, 25°C, wild-type enzyme
2.23
gamma-dodecanolactone
pH 8.3, 25°C, wild-type enzyme
17.6
gamma-heptanolactone
pH 8.3, 25°C, wild-type enzyme
1.88
gamma-nonalactone
pH 8.3, 25°C, wild-type enzyme
2.36 - 349
gamma-undecanolactone
0.106 - 31.6
N-(3-oxodecanoyl)-L-homoserine lactone
2.2 - 121
N-(3-oxododecanoyl)-L-homoserine lactone
0.15
N-(3-oxohexanoyl)-L-homoserine lactone
pH 8.3, 25°C, wild-type enzyme
0.069
N-(3-oxohexanoyl)homoserine lactone
pH 8.3, 25°C, wild-type enzyme
4.39
N-(3-oxooctanoyl)-L-homoserine lactone
pH 8.3, 25°C, wild-type enzyme
1.63
N-(3-oxooctanoyl)homoserine lactone
pH 8.3, 25°C, wild-type enzyme
0.012
N-butanoylhomoserine lactone
pH 8.3, 25°C, wild-type enzyme
4.9
N-dodecanoylhomoserine lactone
pH 8.3, 25°C, wild-type enzyme
0.78
N-hexanoylhomoserine lactone
pH 8.3, 25°C, wild-type enzyme
6.9
N-octanoylhomoserine lactone
pH 8.3, 25°C, wild-type enzyme
0.519 - 12.1
paraoxon
Ki VALUE [mM]
INHIBITOR
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.789 - 7.4
delta-undecanolactone
pH OPTIMUM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
TEMPERATURE OPTIMUM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
ORGANISM
COMMENTARY hide
LITERATURE
UNIPROT
SEQUENCE DB
SOURCE
CRYSTALLIZATION (Commentary)
ORGANISM
UNIPROT
LITERATURE
hanging drop vapor diffusion method, in order to understand the structural consequences of variations at position 263, the crystal structures of the mutant enzymes (W263F, W263M, W263L, W263I, W263V, W263T) is solved
PROTEIN VARIANTS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
W263F
mutant exhibits a lower Tm-value compared to the wild-type enzyme. Catalytic efficiency (kcat/Km) of paraoxon increases 23.3fold compared to wild-type value. 1.3fold increase in catalytic efficiency (kcat/Km) of N-(3-oxododecanoyl)-L-homoserine lactone
W263I
mutant exhibits a lower Tm-value compared to the wild-type enzyme. 45.5fold increase in catalytic efficiency (kcat/Km) of N-(3-oxododecanoyl)-L-homoserine lactone
W263L
mutant exhibits a lower Tm-value compared to the wild-type enzyme. Catalytic efficiency (kcat/Km) of paraoxon increases 4.6fold compared to wild-type value
W263M
mutant exhibits a lower Tm-value compared to the wild-type enzyme. Catalytic efficiency (kcat/Km) of paraoxon increases 14.1fold compared to wild-type value
W263T
mutant exhibits a lower Tm-value compared to the wild-type enzyme. 21.2fold increase in catalytic efficiency (kcat/Km) of N-(3-oxododecanoyl)-L-homoserine lactone
W263V
mutant exhibits a lower Tm-value compared to the wild-type enzyme. 54.5fold increase in catalytic efficiency (kcat/Km) of N-(3-oxododecanoyl)-L-homoserine lactone
TEMPERATURE STABILITY
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
84
Tm-value of mutant enzyme W263L
92
Tm-value of mutant enzyme W263L
additional information
PURIFICATION (Commentary)
ORGANISM
UNIPROT
LITERATURE
REF.
AUTHORS
TITLE
JOURNAL
VOL.
PAGES
YEAR
ORGANISM (UNIPROT)
PUBMED ID
SOURCE
Hiblot, J.; Gotthard, G.; Elias, M.; Chabriere, E.
Differential active site loop conformations mediate promiscuous activities in the lactonase SsoPox
PLoS One
8
e75272
2013
Saccharolobus solfataricus (Q97VT7), Saccharolobus solfataricus, Saccharolobus solfataricus P2 (Q97VT7)
Manually annotated by BRENDA team