Information on EC 3.1.1.88 - pyrethroid hydrolase

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The expected taxonomic range for this enzyme is: Bacteria, Eukaryota, Archaea

EC NUMBER
COMMENTARY hide
3.1.1.88
-
RECOMMENDED NAME
GeneOntology No.
pyrethroid hydrolase
REACTION
REACTION DIAGRAM
COMMENTARY hide
ORGANISM
UNIPROT
LITERATURE
trans-permethrin + H2O = (3-phenoxyphenyl)methanol + (1S,3R)-3-(2,2-dichloroethenyl)-2,2-dimethylcyclopropanecarboxylate
show the reaction diagram
-
-
-
-
SYSTEMATIC NAME
IUBMB Comments
pyrethroid-ester hydrolase
The enzyme is involved in degradation of pyrethroid pesticides. The enzymes from Sphingobium sp., Klebsiella sp. and Aspergillus niger hydrolyse cis-permethrin at approximately equal rate to trans-permethrin [1-3]. The enzyme from mouse hydrolyses trans-permethrin at a rate about 22-fold higher than cis-permethrin [4].
CAS REGISTRY NUMBER
COMMENTARY hide
77114-04-6
-
ORGANISM
COMMENTARY hide
LITERATURE
UNIPROT
SEQUENCE DB
SOURCE
-
-
-
Manually annotated by BRENDA team
-
-
-
Manually annotated by BRENDA team
gene MdalphaE7
-
-
Manually annotated by BRENDA team
-
UniProt
Manually annotated by BRENDA team
GENERAL INFORMATION
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
physiological function
-
overexpression of gene MdalphaE7 in CRR strains leads to resistance versus pyrethroid
SUBSTRATE
PRODUCT                       
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate) hide
LITERATURE
(Substrate)
COMMENTARY
(Product) hide
LITERATURE
(Product)
Reversibility
r=reversible
ir=irreversible
?=not specified
(alphaR)-fenpropathrin + H2O
3-phenoxybenzaldehyde + 2,2,3,3-tetramethylcyclopropanecarboxylate
show the reaction diagram
both stereoisomers of fenpropathrin: (alphaR)- and (alphaS)-fenpropathrin are hydrolyzed at an appropriately equal rate
-
-
?
(alphaR,2R)-fenvalerate + H2O
3-phenoxybenzaldehyde + (2R)-2-(4-chlorophenyl)-3-methylbutanoate
show the reaction diagram
the four stereoisomers of fenvalerate: (alphaS,2R)-fenvalerate, (alphaR,2S)-fenvalerate, (alphaS,2S)-fenvalerate and (alphaR,2R)-fenvalerate are hydrolyzed at an appropriately equal rate
-
-
?
(alphaR,2S)-fenvalerate + H2O
3-phenoxybenzaldehyde + (2S)-2-(4-chlorophenyl)-3-methylbutanoate
show the reaction diagram
the four stereoisomers of fenvalerate: (alphaS,2R)-fenvalerate, (alphaR,2S)-fenvalerate, (alphaS,2S)-fenvalerate and (alphaR,2R)-fenvalerate are hydrolyzed at an appropriately equal rate
-
-
?
(alphaS)-fenpropathrin + H2O
3-phenoxybenzaldehyde + 2,2,3,3-tetramethylcyclopropanecarboxylate
show the reaction diagram
both stereoisomers of fenpropathrin: (alphaR)- and (alphaS)-fenpropathrin are hydrolyzed at an appropriately equal rate
-
-
?
(alphaS,2R)-fenvalerate + H2O
3-phenoxybenzaldehyde + (2R)-2-(4-chlorophenyl)-3-methylbutanoate
show the reaction diagram
the four stereoisomers of fenvalerate: (alphaS,2R)-fenvalerate, (alphaR,2S)-fenvalerate, (alphaS,2S)-fenvalerate and (alphaR,2R)-fenvalerate are hydrolyzed at an appropriately equal rate
-
-
?
(alphaS,2S)-fenvalerate + H2O
3-phenoxybenzaldehyde + (2S)-2-(4-chlorophenyl)-3-methylbutanoate
show the reaction diagram
the four stereoisomers of fenvalerate: (alphaS,2R)-fenvalerate, (alphaR,2S)-fenvalerate, (alphaS,2S)-fenvalerate and (alphaR,2R)-fenvalerate are hydrolyzed at an appropriately equal rate
-
-
?
(R/S)-alpha-cyano (6-methoxy-2-naphthyl)-methyl(R/S)-trans/cis-3-(2,2-dibromovinyl)-2,2-dimethyl cyclopropane carboxylate + H2O
?
show the reaction diagram
-
deltamethrin-like substrate
-
-
?
(R/S)-alpha-cyano (6-methoxy-2-naphthyl)-methyl(R/S)-trans/cis-3-(2,2-dichlorovinyl)-2,2-dimethyl cyclopropane carboxylate + H2O
?
show the reaction diagram
-
cypermethrin-like substrate
-
-
?
4-nitrophenyl acetate + H2O
4-nitrophenol + acetate
show the reaction diagram
-
-
-
-
?
4-nitrophenyl butyrate + H2O
4-nitrophenol + butyrate
show the reaction diagram
-
-
-
-
?
4-nitrophenyl caproate + H2O
4-nitrophenol + caproate
show the reaction diagram
-
-
-
-
?
4-nitrophenyl caprylate + H2O
4-nitrophenol + caprylate
show the reaction diagram
-
-
-
-
?
4-nitrophenyl decanoate + H2O
4-nitrophenol + decanoate
show the reaction diagram
-
-
-
-
?
4-nitrophenyl laurate + H2O
4-nitrophenyl + laurate
show the reaction diagram
-
-
-
-
?
beta-cyfluthrin + H2O
?
show the reaction diagram
-
-
-
-
?
beta-cypermethrin + H2O
?
show the reaction diagram
bifenthrin + H2O
(2-methylbiphenyl-3-yl)methanol + 3-[(1Z)-2-chloro-3,3,3-trifluoroprop-1-en-1-yl]-2,2-dimethylcyclopropanecarboxylate
show the reaction diagram
bifenthrin + H2O
?
show the reaction diagram
-
-
-
?
cis-cypermethrin + H2O
3-phenoxybenzaldehyde + (1S,3S)-3-(2,2-dichloroethenyl)-2,2-dimethylcyclopropanecarboxylate
show the reaction diagram
-
-
-
?
cis-permethrin + H2O
(3-phenoxyphenyl)methanol + (1S,3S)-3-(2,2-dichloroethenyl)-2,2-dimethylcyclopropanecarboxylate
show the reaction diagram
-
-
-
?
cyhalothrin + H2O
3-phenoxybenzaldehyde + 3-[(1Z)-2-chloro-3,3,3-trifluoroprop-1-en-1-yl]-2,2-dimethylcyclopropanecarboxylate
show the reaction diagram
-
-
-
?
cyhalothrin + H2O
?
show the reaction diagram
-
-
-
?
cypermethrin + H2O
3-phenoxybenzaldehyde + 3-(2,2-dichloroethenyl)-2,2-dimethylcyclopropanecarboxylate
show the reaction diagram
cypermethrin + H2O
?
show the reaction diagram
-
-
-
?
deltamethrin + H2O
3-phenoxybenzaldehyde + (1R,3R)-3-(2,2-dibromoethenyl)-2,2-dimethylcyclopropanecarboxylate
show the reaction diagram
deltamethrin + H2O
?
show the reaction diagram
-
-
-
-
?
fenpropathrin + H2O
3-phenoxybenzaldehyde + 2,2,3,3-tetramethylcyclopropanecarboxylate
show the reaction diagram
fenpropathrin + H2O
?
show the reaction diagram
-
-
-
?
fenvalerate + H2O
3-phenoxybenzaldehyde + 2-(4-chlorophenyl)-3-methylbutanoic acid
show the reaction diagram
lambda-cyhalothrin + H2O
?
show the reaction diagram
-
-
-
-
?
permethrin + H2O
3-phenoxybenzyl alcohol + 3-(2,2-dichlorovinyl)-2,2-dimethylcyclopropanecarboxylate
show the reaction diagram
-
fenpropathrin is the most preferred substrate. Whereas the hydrolysis rates toward fenpropathrin, permethrin and cypermethrin are not significantly different, fenvalerate, deltamethrin and bifenthrin are degraded at a considerable lower rate than fenpropathrin
-
-
?
permethrin + H2O
?
show the reaction diagram
trans-cypermethrin + H2O
3-phenoxybenzaldehyde + (1S,3R)-3-(2,2-dichloroethenyl)-2,2-dimethylcyclopropanecarboxylate
show the reaction diagram
-
-
-
?
trans-permethrin + H2O
(3-phenoxyphenyl)methanol + (1S,3R)-3-(2,2-dichloroethenyl)-2,2-dimethylcyclopropanecarboxylate
show the reaction diagram
-
-
-
?
trans-permethrin + H2O
(3-phenoxyphenyl)methanol + trans-3-(2,2-dichloroethenyl)-2,2-dimethylcyclopropanecarboxylate
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
additional information
?
-
COFACTOR
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
additional information
-
METALS and IONS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
Ag+
-
decreases activity
Hg2+
-
decreases activity
Mg2+
-
increases activity
Zn2+
-
decreases activity
INHIBITORS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
1,10-phenanthroline
-
19% inhibition by 1 mM, 27% inhibition by 2 mM
3-phenoxybenzoic acid
-
inhibits the enzyme in vivo
Diethylpyrocarbonate
0.5 mM, strong inhibition
iodoacetamide
0.5 mM, strong inhibition
malathion
-
0.5 mM, 96% inhibition
N-ethylmaleimide
-
dithiothreitol protects against inhibition
NaF
-
0.1 mM, 20% inhibition
NEM
-
15% inhibition above 1 mM
Ni2+
0.5 mM, strong inhibition
p-chloromercuribenzoate
p-chloromercuribenzoic acid
-
0.5 mM, complete inhibition
phenylmethylsulfonyl fluoride
-
0.5 mM, 99% inhibition
sodium taurocholate
-
0.1 mM, 25% inhibition
tetraethyldiphosphate
-
complete inhibition at 0.1 mM, the enzyme may be a serine esterase
Triton X-100
10 mM, 20-30% inhibition
Tween 80
10 mM, strong inhibition
additional information
-
ACTIVATING COMPOUND
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
KM VALUE [mM]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.000106
(alphaR)-fenpropathrin
pH 7.5, 37C
0.000585
(alphaR,2R)-fenvalerate
pH 7.5, 37C
0.000585
(alphaR,2S)-fenvalerate
pH 7.5, 37C
0.000106
(alphaS)-fenpropathrin
pH 7.5, 37C
0.000585
(alphaS,2R)-fenvalerate
pH 7.5, 37C
0.000585
(alphaS,2S)-fenvalerate
pH 7.5, 37C
0.0141
4-nitrophenyl acetate
-
pH 6.5, 55C
0.0316
4-nitrophenyl butyrate
-
pH 6.5, 55C
0.0576
4-nitrophenyl caproate
-
pH 6.5, 55C
0.0332
4-nitrophenyl caprylate
-
pH 6.5, 55C
0.0997
4-nitrophenyl decanoate
-
pH 6.5, 55C
0.13
4-nitrophenyl laurate
-
pH 6.5, 55C
0.00159
bifenthrin
pH 7.5, 37C
0.000108
cis-cypermethrin
pH 7.5, 37C
0.000065
cis-permethrin
pH 7.5, 37C
0.000348
cyhalothrin
pH 7.5, 37C
0.000788
deltamethrin
pH 7.5, 37C
0.00011
trans-cypermethrin
pH 7.5, 37C
0.000062
trans-permethrin
pH 7.5, 37C
TURNOVER NUMBER [1/s]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
2.61
(alphaR)-fenpropathrin
pH 7.5, 37C
0.91
(alphaR,2R)-fenvalerate
pH 7.5, 37C
0.91
(alphaR,2S)-fenvalerate
pH 7.5, 37C
2.61
(alphaS)-fenpropathrin
pH 7.5, 37C
0.91
(alphaS,2R)-fenvalerate
pH 7.5, 37C
0.91
(alphaS,2S)-fenvalerate
pH 7.5, 37C
289.1
4-nitrophenyl acetate
-
pH 6.5, 55C
163.3
4-nitrophenyl butyrate
-
pH 6.5, 55C
88.9
4-nitrophenyl caproate
-
pH 6.5, 55C
149.7
4-nitrophenyl caprylate
-
pH 6.5, 55C
69.1
4-nitrophenyl decanoate
-
pH 6.5, 55C
49.1
4-nitrophenyl laurate
-
pH 6.5, 55C
0.44
bifenthrin
pH 7.5, 37C
2.57
cis-cypermethrin
pH 7.5, 37C
3
cis-permethrin
pH 7.5, 37C
1.28
cyhalothrin
pH 7.5, 37C
0.79
deltamethrin
pH 7.5, 37C
2.53
trans-cypermethrin
pH 7.5, 37C
3.03
trans-permethrin
pH 7.5, 37C
kcat/KM VALUE [1/mMs-1]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
24670
(alphaR)-fenpropathrin
pH 7.5, 37C
1560
(alphaR,2R)-fenvalerate
pH 7.5, 37C
1560
(alphaR,2S)-fenvalerate
pH 7.5, 37C
24670
(alphaS)-fenpropathrin
pH 7.5, 37C
1560
(alphaS,2R)-fenvalerate
pH 7.5, 37C
1560
(alphaS,2S)-fenvalerate
pH 7.5, 37C
1200
(R/S)-alpha-cyano(6-methoxy-2-naphthyl)-methyl acetate
-
pH 8.0, 30C
310 - 1370
4-nitrophenyl acetate
670 - 3410
4-nitrophenyl butanoate
170
4-nitrophenyl dodecanoate
-
pH 7.0, 30C
150 - 13700
4-nitrophenyl hexanoate
100 - 5300
4-nitrophenyl octanoate
6050
4-nitrophenyl pentanoate
-
pH 6.5, 30C
1270 - 1710
4-nitrophenyl propanoate
270
bifenthrin
pH 7.5, 37C
23870
cis-cypermethrin
pH 7.5, 37C
5050 - 46150
cis-permethrin
77
cyano(6-methoxynaphthalen-2-yl)methyl 2-(4-chlorophenyl)-3-methylbutanoate
-
pH 8.0, 30C
40
cyano(6-methoxynaphthalen-2-yl)methyl 3-(2,2-dichloroethenyl)-2,2-dimethylcyclopropanecarboxylate
-
pH 8.0, 30C
3670
cyhalothrin
pH 7.5, 37C
240 - 1370
cypermethrin
9 - 1000
deltamethrin
86 - 113
fenvalerate
55 - 810
malathion
23010
trans-cypermethrin
pH 7.5, 37C
6060 - 48900
trans-permethrin
SPECIFIC ACTIVITY [µmol/min/mg]
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
0.042
-
pH and temperature not specified in the publication
0.84
substrate: bifenthrin, pH 7.5, 37C
1.52
substrate: deltamethrin, pH 7.5, 37C
1.75
substrate: fenvalerate, pH 7.5, 37C
2.46
substrate: cyhalothrin, pH 7.5, 37C
4.86
substrate: trans-cypermethrin, pH 7.5, 37C
4.95
substrate: cis-cypermethrin, pH 7.5, 37C
5.02
substrate: fenpropathrin, pH 7.5, 37C
5.76
substrate: cis-permethrin, pH 7.5, 37C
5.82
substrate: trans-permethrin, pH 7.5, 37C
49.1
-
substrate: 4-nitrophenyl laurate, pH 6.5, 55C
69.1
-
substrate: 4-nitrophenyl decanoate, pH 6.5, 55C
88.9
-
substrate: 4-nitrophenyl caproate, pH 6.5, 55C
149.7
-
substrate: 4-nitrophenyl caprylate, pH 6.5, 55C
163.3
-
substrate: 4-nitrophenyl butyrate, pH 6.5, 55C
772.9
-
substrate: 4-nitrophenyl acetate, pH 6.5, 55C
pH OPTIMUM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
8
-
assay at
pH RANGE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
6 - 8
-
more than 75% of maximal activity at pH 6.0 and at pH 8.0
TEMPERATURE OPTIMUM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
pI VALUE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
MOLECULAR WEIGHT
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
16000
-
x * 16000, SDS-PAGE
25000
-
SDS-PAGE
30800
-
calculated from cDNA
30835
1 * 30835, calculated from sequence
61000
-
gel filtration
SUBUNITS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
monomer
additional information
-
MdalphaE7 structure homology modelling, overview
pH STABILITY
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
4.5 - 8.5
-
-
732458
5.5 - 9
8 - 10
80C, 60 min, the enzyme maintains over 80% of its maximal activity
725749
TEMPERATURE STABILITY
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
37
-
8 h, enzyme retains over 80% of its activity
60
1 h, 45% loss of activity
65
-
nearly completely inactivated
70
1 h, complete inactivation
90
half-life: 180 min
STORAGE STABILITY
ORGANISM
UNIPROT
LITERATURE
25C,10 weeks, 32% loss of activity
-
4C, 10 weeks, 6% loss of activity
-
Purification/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
using Ni-NTA chromatography
Cloned/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
expressed in Escherichia coli as a His-tagged fusion protein
expression in Escherichia coli BL21
gene MdalphaE7, DNA and amino acid sequence determination and analysis, quantitative real-time PCR expression analysis
-
gene pytH, expression in Sphingobium sp. strain BA3 using vector pRK600. The engineered strain can degrade fenpropathin to a higher degree than the wild-type strain JZ-2, and can degrade 3-phenoxybenzoic acid. The inhibtion of pyrethroid hydrolase by 3-phenoxybenzoic acid is eliminated
-
EXPRESSION
ORGANISM
UNIPROT
LITERATURE
induced by trans-permethrin in the medium
-
APPLICATION
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
degradation
environmental protection