Information on EC 3.5.1.97 - acyl-homoserine-lactone acylase

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The enzyme appears in viruses and cellular organisms

EC NUMBER
COMMENTARY hide
3.5.1.97
-
RECOMMENDED NAME
GeneOntology No.
acyl-homoserine-lactone acylase
-
REACTION
REACTION DIAGRAM
COMMENTARY hide
ORGANISM
UNIPROT
LITERATURE
an N-acyl-L-homoserine lactone + H2O = L-homoserine lactone + a carboxylate
show the reaction diagram
REACTION TYPE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
hydrolysis of amide bond
-
SYSTEMATIC NAME
IUBMB Comments
N-acyl-L-homoserine-lactone amidohydrolase
Acyl-homoserine lactones (AHLs) are produced by a number of bacterial species and are used by them to regulate the expression of virulence genes in a process known as quorum-sensing. Each bacterial cell has a basal level of AHL and, once the population density reaches a critical level, it triggers AHL-signalling which, in turn, initiates the expression of particular virulence genes. Plants or animals capable of degrading AHLs would have a therapeutic advantage in avoiding bacterial infection as they could prevent AHL-signalling and the expression of virulence genes in quorum-sensing bacteria. This quorum-quenching enzyme removes the fatty-acid side chain from the homoserine lactone ring of AHL-dependent quorum-sensing signal molecules. It has broad specificity for AHLs with side changes ranging in length from 11 to 14 carbons. Substituents at the 3'-position, as found in N-(3-oxododecanoyl)-L-homoserine lactone, do not affect this activity.
CAS REGISTRY NUMBER
COMMENTARY hide
857396-91-9
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ORGANISM
COMMENTARY hide
LITERATURE
UNIPROT
SEQUENCE DB
SOURCE
activated-sludge isolate, gene amiE
UniProt
Manually annotated by BRENDA team
activated-sludge isolate, gene amiE
UniProt
Manually annotated by BRENDA team
strain PCC 7120, previously Nostoc sp.
-
-
Manually annotated by BRENDA team
-
-
-
Manually annotated by BRENDA team
-
-
-
Manually annotated by BRENDA team
the virulence of Pseudomonas aeruginosa PAO1 is analyzed in a Caenorhabditis elegans infection model
-
-
Manually annotated by BRENDA team
strain B728a, strain BHSL, strain HacA-, strain HacB-, strain HacA-B-
UniProt
Manually annotated by BRENDA team
an important soil-borne plant pathogen with an extensive host range
-
-
Manually annotated by BRENDA team
strain XJ12B, gene aiiD, isolated from a mixed-species biofilm
-
-
Manually annotated by BRENDA team
strain XJ12B, gene aiiD, isolated from a mixed-species biofilm
-
-
Manually annotated by BRENDA team
GENERAL INFORMATION
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
evolution
physiological function
SUBSTRATE
PRODUCT                       
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate) hide
LITERATURE
(Substrate)
COMMENTARY
(Product) hide
LITERATURE
(Product)
Reversibility
r=reversible
ir=irreversible
?=not specified
N-(3-hydroxybutyryl)-L-homoserine lactone + H2O
?
show the reaction diagram
-
-
-
-
?
N-(3-hydroxydecanoyl)-L-homoserine lactone + H2O
?
show the reaction diagram
-
-
-
-
?
N-(3-hydroxydodecanoyl)-L-homoserine lactone + H2O
?
show the reaction diagram
-
-
-
-
?
N-(3-hydroxyhexanoyl)-L-homoserine lactone + H2O
?
show the reaction diagram
-
-
-
-
?
N-(3-hydroxyoctanoyl)-L-homoserine lactone + H2O
?
show the reaction diagram
-
-
-
-
?
N-(3-hydroxytetradecanoyl)-L-homoserine lactone + H2O
?
show the reaction diagram
-
-
-
-
?
N-(3-oxobutyryl)-L-homoserine lactone + H2O
?
show the reaction diagram
-
-
-
-
?
N-(3-oxodecanoyl)-L-homoserine lactone + H2O
?
show the reaction diagram
-
-
-
-
?
N-(3-oxodecanoyl)-L-homoserine lactone + H2O
L-homoserine lactone + 3-oxodecanoate
show the reaction diagram
-
-
-
-
?
N-(3-oxododecanoyl)-L-homoserine lactone + H2O
?
show the reaction diagram
-
-
-
-
?
N-(3-oxododecanoyl)-L-homoserine lactone + H2O
L-homoserine lactone + 3-oxodecanoate
show the reaction diagram
-
-
-
-
?
N-(3-oxododecanoyl)-L-homoserine lactone + H2O
L-homoserine lactone + 3-oxododecanoate
show the reaction diagram
N-(3-oxohexanoyl)-DL-homoserine lactone + H2O
homoserine lactone + 3-oxohexanoate
show the reaction diagram
0.5 microM, assay at 28C, pH 7.0, 1 h
-
-
?
N-(3-oxohexanoyl)-L-homoserine lactone + H2O
?
show the reaction diagram
-
-
-
-
?
N-(3-oxohexanoyl)-L-homoserine lactone + H2O
homoserine lactone + 3-oxooctanoate
show the reaction diagram
N-(3-oxohexanoyl)-L-homoserine lactone + H2O
L-homoserine lactone + 3-oxohexanoate
show the reaction diagram
N-(3-oxooctanoyl)-DL-homoserine lactone + H2O
homoserine lactone + 3-oxooctanoate
show the reaction diagram
0.5 microM, assay at 28C, pH 7.0, 1 h
-
-
?
N-(3-oxooctanoyl)-L-homoserine lactone + H2O
?
show the reaction diagram
-
-
-
-
?
N-(3-oxooctanoyl)-L-homoserine lactone + H2O
homoserine lactone + 3-oxohexanoate
show the reaction diagram
N-(3-oxooctanoyl)-L-homoserine lactone + H2O
L-homoserine lactone + 3-oxooctanoate
show the reaction diagram
N-(3-oxotetradecanoyl)-L-homoserine lactone + H2O
?
show the reaction diagram
-
-
-
-
?
N-(3-oxotetradecanoyl)-L-homoserine lactone + H2O
L-homoserine lactone + 3-oxotetradecanoate
show the reaction diagram
-
-
-
-
?
N-3-oxodecanoyl-(S)-homoserine lactone + H2O
(S)-homoserine + 3-oxodecanoic acid
show the reaction diagram
-
-
-
-
?
N-3-oxodecanoyl-(S)-homoserine lactone + H2O
(S)-homoserine lactone + 3-oxodecanoic acid
show the reaction diagram
N-3-oxodecanoyl-L-homoserine lactone + H2O
L-homoserine lactone + 3-oxodecanoic acid
show the reaction diagram
-
-
-
?
N-3-oxododecanoyl-(S)-homoserine lactone + H2O
(S)-homoserine + 3-oxododecanoic acid
show the reaction diagram
-
-
-
-
?
N-3-oxododecanoyl-L-homoserine lactone + H2O
L-homoserine + 3-oxododecanoic acid
show the reaction diagram
-
-
-
-
?
N-3-oxooctanoyl-DL-homoserine lactone + H2O
homoserine lactone + 3-oxooctanoate
show the reaction diagram
0.5 microM, assay at 28C, pH 7.0, 3 h
-
-
?
N-acyl-(S)-homoserine lactone + H2O
(S)-homoserine lactone + carboxylic acid
show the reaction diagram
N-butanoyl-L-homoserine lactone + H2O
L-homoserine lactone + butanoate
show the reaction diagram
N-butyryl homoserine lactone + H2O
homoserine lactone + butanoate
show the reaction diagram
0.5 microM, assay at 28C, pH 7.0, 1 h
-
-
?
N-butyryl-L-homoserine lactone + H2O
?
show the reaction diagram
-
-
-
-
?
N-decanoyl-DL-homoserine lactone + H2O
DL-homoserine lactone + decanoate
show the reaction diagram
-
-
-
-
?
N-decanoyl-DL-homoserine lactone + H2O
homoserine lactone + decanoate
show the reaction diagram
N-decanoyl-L-homoserine lactone + H2O
?
show the reaction diagram
-
-
-
-
?
N-decanoyl-L-homoserine lactone + H2O
L-homoserine lactone + decanoate
show the reaction diagram
N-decanoyl-L-homoserine lactone + H2O
L-homoserine lactone + decanoic acid
show the reaction diagram
-
-
-
-
?
N-dodecanoyl-(S)-homoserine lactone + H2O
(S)-homoserine + dodecanoic acid
show the reaction diagram
-
-
-
-
?
N-dodecanoyl-DL-homoserine lactone + H2O
DL-homoserine lactone + dodecanoate
show the reaction diagram
-
-
-
-
?
N-dodecanoyl-DL-homoserine lactone + H2O
homoserine lactone + dodecanoate
show the reaction diagram
N-dodecanoyl-L-homoserine lactone + H2O
?
show the reaction diagram
-
-
-
-
?
N-dodecanoyl-L-homoserine lactone + H2O
L-homoserine lactone + dodecanoate
show the reaction diagram
N-heptanoyl-(S)-homoserine lactone + H2O
(S)-homoserine + heptanoic acid
show the reaction diagram
-
-
-
-
?
N-heptanoyl-DL-homoserine lactone + H2O
DL-homoserine lactone + heptanoate
show the reaction diagram
-
-
-
-
?
N-heptanoyl-L-homoserine lactone + H2O
L-homoserine lactone + heptanoic acid
show the reaction diagram
-
-
determined by ESI-MS analysis
-
?
N-hexanoyl-DL-homoserine lactone + H2O
homoserine lactone + hexanoate
show the reaction diagram
0.5 microM, assay at 28C, pH 7.0, 1 h
-
-
?
N-hexanoyl-L-homoserine lactone + H2O
?
show the reaction diagram
-
-
-
-
?
N-hexanoyl-L-homoserine lactone + H2O
L-homoserine lactone + hexanoate
show the reaction diagram
N-octanoyl-(S)-homoserine lactone + H2O
(S)-homoserine + octanoic acid
show the reaction diagram
-
-
-
-
?
N-octanoyl-DL-homoserine lactone + H2O
DL-homoserine lactone + octanoate
show the reaction diagram
-
-
-
-
?
N-octanoyl-DL-homoserine lactone + H2O
homoserine lactone + octanoate
show the reaction diagram
N-octanoyl-L-homoserine lactone + H2O
?
show the reaction diagram
-
-
-
-
?
N-octanoyl-L-homoserine lactone + H2O
L-homoserine lactone + octanoate
show the reaction diagram
N-octanoyl-L-homoserine lactone + H2O
L-homoserine lactone + octanoic acid
show the reaction diagram
-
-
-
-
?
N-tetradecanoyl-(S)-homoserine lactone + H2O
(S)-homoserine + tetradecanoic acid
show the reaction diagram
-
-
-
-
?
N-tetradecanoyl-DL-homoserine lactone + H2O
DL-homoserine lactone + tetradecanoate
show the reaction diagram
-
-
-
-
?
N-tetradecanoyl-L-homoserine lactone + H2O
?
show the reaction diagram
-
-
-
-
?
N-undecanoyl-(S)-homoserine lactone + H2O
(S)-homoserine + undecanoic acid
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
N-3-oxododecanoyl-(S)-homoserine lactone + H2O
(S)-homoserine + 3-oxododecanoic acid
show the reaction diagram
-
-
-
-
?
N-acyl-(S)-homoserine lactone + H2O
(S)-homoserine lactone + carboxylic acid
show the reaction diagram
N-dodecanoyl-(S)-homoserine lactone + H2O
(S)-homoserine + dodecanoic acid
show the reaction diagram
-
-
-
-
?
N-tetradecanoyl-(S)-homoserine lactone + H2O
(S)-homoserine + tetradecanoic acid
show the reaction diagram
-
-
-
-
?
N-undecanoyl-(S)-homoserine lactone + H2O
(S)-homoserine + undecanoic acid
show the reaction diagram
-
-
-
-
?
additional information
?
-
METALS and IONS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
INHIBITORS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
Ag+
complete inhibition at 1 mM
Cr3+
29.1% residual activity at 1 mM
Cu2+
68.5% residual activity at 1 mM
Hg2+
complete inhibition at 1 mM
Li+
65.8% residual activity at 10 mM
Pb2+
87.5% residual activity at 10 mM
SDS
complete inhibition at 10 mM
ACTIVATING COMPOUND
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
2-mercaptoethanol
112.2% activity at 1 mM
kcat/KM VALUE [1/mMs-1]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
78
N-(3-oxododecanoyl)-L-homoserine lactone
Pseudomonas aeruginosa
-
in 0.1 M phosphate buffer pH 7.4, at 30C
3761
1.4
N-octanoyl-L-homoserine lactone
Pseudomonas aeruginosa
-
in 0.1 M phosphate buffer pH 7.4, at 30C
3740
SPECIFIC ACTIVITY [µmol/min/mg]
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
0.0019
substrate N-butyryl homoserine lactone
0.0049
substrate N-(3-oxohexanoyl)-DL-homoserine lactone
0.0276
substrate N-hexanoyl-DL-homoserine lactone
0.0406
substrate N-decanoyl-DL-homoserine lactone
0.0408
substrate N-(3-oxooctanoyl)-DL-homoserine lactone
0.0463
substrate N-octanoyl-DL-homoserine lactone
2.995
purified enzyme, using N-(3-oxooctanoyl)-L-homoserine lactone as the substrate, at pH 8.0 and 25C
1100
substrate N-3-oxooctanoyl-DL-homoserine lactone
3200
substrate N-octanoyl-DL-homoserine lactone
3800
substrate N-decanoyl-DL-homoserine lactone
pH RANGE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
6.5 - 8.9
more than 73% of the maximum activity at pH 6.5-8.9
TEMPERATURE OPTIMUM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
TEMPERATURE RANGE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
0 - 35
at 0C and 20-35C, the enzyme maintains more than 60% of the highest activity at 20C
SOURCE TISSUE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
SOURCE
additional information
-
in the Caenorhabditis elegans infection model it is observed that larval stage 1 to 3 benefit much more from the protection by PvdQ than larval stage 4 worms
Manually annotated by BRENDA team
PDB
SCOP
CATH
ORGANISM
UNIPROT
Pseudomonas aeruginosa (strain ATCC 15692 / DSM 22644 / CIP 104116 / JCM 14847 / LMG 12228 / 1C / PRS 101 / PAO1)
Pseudomonas aeruginosa (strain ATCC 15692 / DSM 22644 / CIP 104116 / JCM 14847 / LMG 12228 / 1C / PRS 101 / PAO1)
Pseudomonas aeruginosa (strain ATCC 15692 / DSM 22644 / CIP 104116 / JCM 14847 / LMG 12228 / 1C / PRS 101 / PAO1)
Pseudomonas aeruginosa (strain ATCC 15692 / DSM 22644 / CIP 104116 / JCM 14847 / LMG 12228 / 1C / PRS 101 / PAO1)
Pseudomonas aeruginosa (strain ATCC 15692 / DSM 22644 / CIP 104116 / JCM 14847 / LMG 12228 / 1C / PRS 101 / PAO1)
Pseudomonas aeruginosa (strain ATCC 15692 / DSM 22644 / CIP 104116 / JCM 14847 / LMG 12228 / 1C / PRS 101 / PAO1)
Pseudomonas aeruginosa (strain ATCC 15692 / DSM 22644 / CIP 104116 / JCM 14847 / LMG 12228 / 1C / PRS 101 / PAO1)
Pseudomonas aeruginosa (strain ATCC 15692 / DSM 22644 / CIP 104116 / JCM 14847 / LMG 12228 / 1C / PRS 101 / PAO1)
Pseudomonas aeruginosa (strain ATCC 15692 / DSM 22644 / CIP 104116 / JCM 14847 / LMG 12228 / 1C / PRS 101 / PAO1)
Pseudomonas aeruginosa (strain ATCC 15692 / DSM 22644 / CIP 104116 / JCM 14847 / LMG 12228 / 1C / PRS 101 / PAO1)
Pseudomonas aeruginosa (strain ATCC 15692 / DSM 22644 / CIP 104116 / JCM 14847 / LMG 12228 / 1C / PRS 101 / PAO1)
Pseudomonas aeruginosa (strain ATCC 15692 / DSM 22644 / CIP 104116 / JCM 14847 / LMG 12228 / 1C / PRS 101 / PAO1)
Pseudomonas aeruginosa (strain ATCC 15692 / DSM 22644 / CIP 104116 / JCM 14847 / LMG 12228 / 1C / PRS 101 / PAO1)
Pseudomonas aeruginosa (strain ATCC 15692 / DSM 22644 / CIP 104116 / JCM 14847 / LMG 12228 / 1C / PRS 101 / PAO1)
Pseudomonas aeruginosa (strain ATCC 15692 / DSM 22644 / CIP 104116 / JCM 14847 / LMG 12228 / 1C / PRS 101 / PAO1)
Pseudomonas aeruginosa (strain ATCC 15692 / DSM 22644 / CIP 104116 / JCM 14847 / LMG 12228 / 1C / PRS 101 / PAO1)
Pseudomonas aeruginosa (strain ATCC 15692 / DSM 22644 / CIP 104116 / JCM 14847 / LMG 12228 / 1C / PRS 101 / PAO1)
Pseudomonas aeruginosa (strain ATCC 15692 / DSM 22644 / CIP 104116 / JCM 14847 / LMG 12228 / 1C / PRS 101 / PAO1)
Pseudomonas aeruginosa (strain ATCC 15692 / DSM 22644 / CIP 104116 / JCM 14847 / LMG 12228 / 1C / PRS 101 / PAO1)
MOLECULAR WEIGHT
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
19000
alphabeta, 1 * 19000 + 1 * 60000, SDS-PAGE
22000
alphabeta, 1 * 22000 + 1 * 600000, SDS-PAGE
26000
-
1 * 26000 (C-terminally processed alpha-subunit) + 1 * 60000 (beta-subunit), SDS-PAGE
28140
x * 28140, calculated from amino acid sequence
31500
x * 31500, deglycosylated enzyme, based on SDS-PAGE
33600
x * 33600, glycosylated enzyme, based on SDS-PAGE
88000
-
SDS-PAGE, recombinant protein
88650
-
predicted molecular mass of the recombinant protein
90000
-
SDS-PAGE, recombinant enzyme
600000
alphabeta, 1 * 22000 + 1 * 600000, SDS-PAGE
SUBUNITS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
dimer
alphabeta, 1 * 19000 + 1 * 60000, SDS-PAGE; alphabeta, 1 * 22000 + 1 * 600000, SDS-PAGE
heterodimer
-
1 * 26000 (C-terminally processed alpha-subunit) + 1 * 60000 (beta-subunit), SDS-PAGE
POSTTRANSLATIONAL MODIFICATION
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
glycoprotein
Crystallization/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
1.8 A resolution. PvdQ has a typical alpha/beta heterodimeric Ntn-hydrolase fold. It has a large, hydrophobic binding pocket, ideally suited to recognize C12 fatty acid-like chains of N-acylhomoserine lactones. Binding of a C12 fatty acid or a 3-oxo-C12 fatty acid induces subtle conformational changes to accommodate the aliphatic chain. PvdQ is the first structurally characterized Ntn-hydrolase within this family to have any disulfide bridges. The disulfides are located in both the alpha- and beta-chain on the periphery of the protein
pH STABILITY
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
6 - 12
the enzyme is stable at pH 6.0-12.0, retaining more than 70% activity after pre-incubation at 37C for 1 h
720378
TEMPERATURE STABILITY
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
70
recombinant enzyme retains more than 80% of the initial activity after preincubation at 70C for 30 min
GENERAL STABILITY
ORGANISM
UNIPROT
LITERATURE
after incubation with trypsin, subtilisin A, collagenase and proleather at 37C for 30 or 60 min, the enzyme maintains or enhances its enzymatic activity
STORAGE STABILITY
ORGANISM
UNIPROT
LITERATURE
0C, purified enzyme, 3 months, 1.6% loss of activity
Purification/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
a two-step purification protocol, anion exchange chromatography and hydrophobic interaction chromatography
-
ammonium sulfate precipitation and anion exchange chromatography
Ni-NTA agarose column chromatography
-
recombinant enzyme from Escherichia coli strain DH10B by several chromatographic steps
-
Cloned/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
cloned and expressed in Escherichia coli DH10B
-
cloned and overexpressed
expressed in Escherichia coli
expressed in Escherichia coli BL21(DE3) cells
-
expressed in Escherichia coli DH5alpha cells
-
expressed in Escherichia coli Origami cells
-
expressed in Pichia pastoris strain GS115
expression in Escherichia coli
expression in Escherichia coli strain BL21 and in Vibrio anguillarum strain TB0008
expression in Escherichia coli strain DH10B
-
gene aiiD, DNA and amino acid sequence determination and analysis, functional expression in Escherichia coli strain DH5alpha, expression of AiiD in Pseudomonas aeruginosa strain PAO1 without showing catalytic function, but reducing the ability of the bacterium to exhibit quorum-regulated swarming motility, the bacterium is attenuated in nematode killing
-
gene amiE, from genomic library, DNA and amino acid sequence determination and analysis, phylogenetic tree, sequence comparisons, amiE is transferred by a putative transposon, cloning in Escherichia coli strain DHalpha, recombinant expression in Pseudomonas aeruginosa strain PAO1 leading to reduced N-acyl-L-homoserine lactone accumulation and elastase activity
ENGINEERING
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
additional information
-
the strain PAO1-DELTApvd is shown to be more virulent than the wild-type strain, confirming the role of PvdQ as a virulence-reducing agent
APPLICATION
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
agriculture
biotechnology
additional information
fundamental roles in biofilm formation
Show AA Sequence (279 entries)
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