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Literature summary for 3.1.1.1 extracted from

  • Heidari, R.; Devonshire, A.L.; Campbell, B.E.; Dorrian, S.J.; Oakeshott, J.G.; Russell, R.J.
    Hydrolysis of pyrethroids by carboxylesterases from Lucilia cuprina and Drosophila melanogaster with active sites modified by in vitro mutagenesis (2005), Insect Biochem. Mol. Biol., 35, 597-609.
    View publication on PubMed

Protein Variants

Protein Variants Comment Organism
E217M mutant in anionic site, p1 subsite, pyrethroid hydrolysis similar to wild-type Lucilia cuprina
F309L mutant in acyl pocket p2 subsite, marked increase in pyrethroid hydrolysis both for cis-substrate, strong increase for trans-substrate Lucilia cuprina
F354L mutant in anionic site, p1 subsite, pyrethroid hydrolysis similar to wild-type Lucilia cuprina
F354W mutant in anionic site, p1 subsite, marked increase in pyrethroid hydrolysis both for cis- and trans-substrate Lucilia cuprina
G137D mutant in oxyanion hole, marked decrease in pyrethroid hydrolysis Lucilia cuprina
G137D strong decrease in pyrethroid hydrolysis Drosophila melanogaster
G137E mutant in oxyanion hole, strong decrease in pyrethroid hydrolysis Lucilia cuprina
G137H mutant in oxyanion hole, marked decrease in pyrethroid hydrolysis Lucilia cuprina
G137R mutant in oxyanion hole, pyrethroid hydrolysis similar to wild-type Lucilia cuprina
W251A mutant in acyl pocket p2 subsite, marked increase in pyrethroid hydrolysis both for cis- and trans-substrate Lucilia cuprina
W251G mutant in acyl pocket p2 subsite, marked increase in pyrethroid hydrolysis both for cis- and trans-substrate Lucilia cuprina
W251L marked increase in pyrethroid hydrolysis, trans:cis ratio for preference of substrate is 2:1 compared to 24:1 in wild-type Drosophila melanogaster
W251L mutant in acyl pocket p2 subsite, strong increase in pyrethroid hydrolysis both for cis- and trans-substrate. Trans:cis ratio for preference of substrate is 2:1 compared to 27:1 in wild-type Lucilia cuprina
W251L/F309L mutant in acyl pocket p2 subsite, marked increase in pyrethroid hydrolysis both for cis- and trans-substrate. Trans:cis ratio for preference of substrate is 2:1 compared to 27:1 in wild-type Lucilia cuprina
W251L/G137D mutant in acyl pocket p2 subsite, marked increase in pyrethroid hydrolysis both for cis- and trans-substrate. Trans:cis ratio for preference of substrate is 2:1 compared to 27:1 in wild-type Lucilia cuprina
W251L/P250S mutant in acyl pocket p2 subsite, marked increase in pyrethroid hydrolysis both for cis- and trans-substrate. Trans:cis ratio for preference of substrate is 3:1 compared to 27:1 in wild-type Lucilia cuprina
W251S mutant in acyl pocket p2 subsite, marked increase in pyrethroid hydrolysis both for cis- and trans-substrate Lucilia cuprina
W251T mutant in acyl pocket p2 subsite, marked increase in pyrethroid hydrolysis both for cis- and trans-substrate Lucilia cuprina
Y148F mutant in anionic site, p1 subsite, marked increase in pyrethroid hydrolysis both for cis- and trans-substrate Lucilia cuprina
Y148F/G137D marked decrease in pyrethroid hydrolysis, trans:cis ratio for preference of substrate is 87:1 compared to 24:1 in wild-type Lucilia cuprina

Organism

Organism UniProt Comment Textmining
Drosophila melanogaster
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expression in baculoviral system
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Lucilia cuprina
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expression in baculoviral system
-

Substrates and Products (Substrate)

Substrates Comment Substrates Organism Products Comment (Products) Rev. Reac.
3-phenoxybenzyl (1R,3R)-3-(2,2-dibromovinyl)-2,2-dimethylcyclopropanecarboxylate + H2O i.e. 1R-cis-NRDC157 Drosophila melanogaster (1R,3R)-3-(2,2-dibromovinyl)-2,2-dimethylcyclopropanecarboxylic acid + (3-phenoxyphenyl)methanol
-
?
3-phenoxybenzyl (1R,3R)-3-(2,2-dibromovinyl)-2,2-dimethylcyclopropanecarboxylate + H2O i.e. 1R-cis-NRDC157 Lucilia cuprina (1R,3R)-3-(2,2-dibromovinyl)-2,2-dimethylcyclopropanecarboxylic acid + (3-phenoxyphenyl)methanol
-
?
3-phenoxybenzyl (1R,3S)-3-(2,2-dichlorovinyl)-2,2-dimethylcyclopropanecarboxylate + H2O i.e. 1R-trans-permethrin, strong chiral preference for the 1S over the 1R isomers of permethrin Drosophila melanogaster (1R,3S)-3-(2,2-dichlorovinyl)-2,2-dimethylcyclopropanecarboxylic acid + (3-phenoxyphenyl)methanol
-
?
3-phenoxybenzyl (1R,3S)-3-(2,2-dichlorovinyl)-2,2-dimethylcyclopropanecarboxylate + H2O i.e. 1R-trans-permethrin, strong chiral preference for the 1S over the 1R isomers of permethrin Lucilia cuprina (1R,3S)-3-(2,2-dichlorovinyl)-2,2-dimethylcyclopropanecarboxylic acid + (3-phenoxyphenyl)methanol
-
?
3-phenoxybenzyl (1S,3R)-3-(2,2-dichlorovinyl)-2,2-dimethylcyclopropanecarboxylate + H2O i.e. 1S-trans-permethrin, strong chiral preference for the 1S over the 1R isomers of permethrin Drosophila melanogaster (1S,3R)-3-(2,2-dichlorovinyl)-2,2-dimethylcyclopropanecarboxylic acid + (3-phenoxyphenyl)methanol
-
?
3-phenoxybenzyl (1S,3R)-3-(2,2-dichlorovinyl)-2,2-dimethylcyclopropanecarboxylate + H2O i.e. 1S-trans-permethrin, strong chiral preference for the 1S over the 1R isomers of permethrin Lucilia cuprina (1S,3R)-3-(2,2-dichlorovinyl)-2,2-dimethylcyclopropanecarboxylic acid + (3-phenoxyphenyl)methanol
-
?
3-phenoxybenzyl (1S,3S)-3-(2,2-dibromovinyl)-2,2-dimethylcyclopropanecarboxylate + H2O i.e. 1S-cis-NRDC157 Drosophila melanogaster (1S,3S)-3-(2,2-dibromovinyl)-2,2-dimethylcyclopropanecarboxylic acid + (3-phenoxyphenyl)methanol
-
?
3-phenoxybenzyl (1S,3S)-3-(2,2-dibromovinyl)-2,2-dimethylcyclopropanecarboxylate + H2O i.e. 1S-cis-NRDC157 Lucilia cuprina (1S,3S)-3-(2,2-dibromovinyl)-2,2-dimethylcyclopropanecarboxylic acid + (3-phenoxyphenyl)methanol
-
?