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Literature summary extracted from

  • Summerer, S.; Hanano, A.; Utsumi, S.; Arand, M.; Schuber, F.; Blee, E.
    Stereochemical features of the hydrolysis of 9,10-epoxystearic acid catalysed by plant and mammalian epoxide hydrolases (2002), Biochem. J., 366, 471-480.
    View publication on PubMedView publication on EuropePMC

Activating Compound

EC Number Activating Compound Comment Organism Structure
3.3.2.9 additional information pathogens induce enzyme expression Solanum tuberosum

Cloned(Commentary)

EC Number Cloned (Comment) Organism
3.3.2.9 expression of His-tagged enzyme in Saccharomyces cerevisiae strain WA6, the N-terminal His-tag reduces enzyme activity by 75%, therefore a C-terminal His-tag is used Glycine max

Protein Variants

EC Number Protein Variants Comment Organism
3.3.2.10 E404D site-directed mutagenesis, the mutant enzyme shows unaltered enantioselectivity with stearic acid oxide substrate compared to the wild-type enzyme Rattus norvegicus

KM Value [mM]

EC Number KM Value [mM] KM Value Maximum [mM] Substrate Comment Organism Structure
3.3.2.9 additional information
-
 additional information kinetics Rattus norvegicus
3.3.2.9 additional information
-
 additional information kinetics Triticum aestivum
3.3.2.9 additional information
-
 additional information kinetics Zea mays
3.3.2.9 additional information
-
 additional information kinetics Solanum tuberosum
3.3.2.9 additional information
-
 additional information kinetics Nicotiana tabacum
3.3.2.9 additional information
-
 additional information kinetics Glycine max
3.3.2.9 additional information
-
 additional information kinetics Apium graveolens
3.3.2.9 additional information
-
 additional information kinetics Oryza sativa
3.3.2.9 additional information
-
 additional information kinetics Musa x paradisiaca
3.3.2.10 additional information
-
 additional information kinetics Rattus norvegicus

Localization

EC Number Localization Comment Organism GeneOntology No. Textmining
3.3.2.9 cytosol
-
 Rattus norvegicus 5829
-
3.3.2.9 soluble
-
 Triticum aestivum
-
-
3.3.2.9 soluble
-
 Zea mays
-
-
3.3.2.9 soluble
-
 Solanum tuberosum
-
-
3.3.2.9 soluble
-
 Nicotiana tabacum
-
-
3.3.2.9 soluble
-
 Glycine max
-
-
3.3.2.9 soluble
-
 Apium graveolens
-
-
3.3.2.9 soluble
-
 Oryza sativa
-
-
3.3.2.9 soluble
-
 Musa x paradisiaca
-
-
3.3.2.10 microsome
-
 Rattus norvegicus
-
-

Molecular Weight [Da]

EC Number Molecular Weight [Da] Molecular Weight Maximum [Da] Comment Organism
3.3.2.9 31000
-
 gel filtration, 2 peaks Apium graveolens
3.3.2.9 62000
-
 gel filtration, 2 peaks Apium graveolens
3.3.2.9 64000
-
 gel filtration Zea mays

Organism

EC Number Organism UniProt Comment Textmining
3.3.2.9 Apium graveolens
-
 var. rapaceum
-
3.3.2.9 Glycine max
-
-
-
3.3.2.9 Musa x paradisiaca
-
-
-
3.3.2.9 Nicotiana tabacum
-
 var. samsun, infected with Tobacco mosaic virus
-
3.3.2.9 Oryza sativa
-
 var. rosa marchetti
-
3.3.2.9 Rattus norvegicus
-
-
-
3.3.2.9 Solanum tuberosum
-
-
-
3.3.2.9 Triticum aestivum
-
 var. kamut
-
3.3.2.9 Zea mays
-
 var. blizzar
-
3.3.2.10 Rattus norvegicus
-
-
-

Purification (Commentary)

EC Number Purification (Comment) Organism
3.3.2.9 preparation of cytosolic fraction by ultracentrifugation Triticum aestivum
3.3.2.9 preparation of cytosolic fraction by ultracentrifugation Solanum tuberosum
3.3.2.9 preparation of cytosolic fraction by ultracentrifugation Nicotiana tabacum
3.3.2.9 preparation of cytosolic fraction by ultracentrifugation Oryza sativa
3.3.2.9 preparation of cytosolic fraction by ultracentrifugation Musa x paradisiaca
3.3.2.9 recombinant His-tagged enzyme from Saccharomyces cerevisiae strain WA6 by nickel affinity chromatography Glycine max
3.3.2.9 to homogeneity from root cytosol Apium graveolens
3.3.2.9 to homogeneity from seedling cytosol Zea mays

Reaction

EC Number Reaction Comment Organism Reaction ID
3.3.2.9 cis-stilbene oxide + H2O = (1R,2R)-1,2-diphenylethane-1,2-diol reaction mechanism, catalytic triad Rattus norvegicus
a
3.3.2.9 cis-stilbene oxide + H2O = (1R,2R)-1,2-diphenylethane-1,2-diol reaction mechanism, catalytic triad Triticum aestivum
a
3.3.2.9 cis-stilbene oxide + H2O = (1R,2R)-1,2-diphenylethane-1,2-diol reaction mechanism, catalytic triad Zea mays
a
3.3.2.9 cis-stilbene oxide + H2O = (1R,2R)-1,2-diphenylethane-1,2-diol reaction mechanism, catalytic triad Solanum tuberosum
a
3.3.2.9 cis-stilbene oxide + H2O = (1R,2R)-1,2-diphenylethane-1,2-diol reaction mechanism, catalytic triad Nicotiana tabacum
a
3.3.2.9 cis-stilbene oxide + H2O = (1R,2R)-1,2-diphenylethane-1,2-diol reaction mechanism, catalytic triad Glycine max
a
3.3.2.9 cis-stilbene oxide + H2O = (1R,2R)-1,2-diphenylethane-1,2-diol reaction mechanism, catalytic triad Apium graveolens
a
3.3.2.9 cis-stilbene oxide + H2O = (1R,2R)-1,2-diphenylethane-1,2-diol reaction mechanism, catalytic triad Oryza sativa
a
3.3.2.9 cis-stilbene oxide + H2O = (1R,2R)-1,2-diphenylethane-1,2-diol reaction mechanism, catalytic triad Musa x paradisiaca
a
3.3.2.10 an epoxide + H2O = a glycol reaction mechanism, catalytic triad Rattus norvegicus
a

Source Tissue

EC Number Source Tissue Comment Organism Textmining
3.3.2.9 fruit pulp
-
 Musa x paradisiaca
-
3.3.2.9 leaf harvested 7 days after inoculation with Erypsiphe graminis Nicotiana tabacum
-
3.3.2.9 liver
-
 Rattus norvegicus
-
3.3.2.9 root
-
 Apium graveolens
-
3.3.2.9 seedling
-
 Triticum aestivum
-
3.3.2.9 seedling
-
 Zea mays
-
3.3.2.9 seedling
-
 Oryza sativa
-
3.3.2.9 tuber
-
 Solanum tuberosum
-
3.3.2.10 liver
-
 Rattus norvegicus
-

Substrates and Products (Substrate)

EC Number Substrates Comment Substrates Organism Products Comment (Products) Rev. Reac.
3.3.2.9 cis-(9R,10S)-epoxystearic acid + H2O
-
 Rattus norvegicus threo-(9R,10R)-dihydroxystearic acid + threo-(9S,10S)-dihydroxystearic acid enantioselective production of 80% (9R,10R)-diol and 20% (9S,10S)-diol ?
3.3.2.9 cis-(9R,10S)-epoxystearic acid + H2O
-
 Zea mays threo-(9R,10R)-dihydroxystearic acid + threo-(9S,10S)-dihydroxystearic acid enantioselective production of 84% (9R,10R)-diol and 16% (9S,10S)-diol ?
3.3.2.9 cis-(9R,10S)-epoxystearic acid methyl ester + H2O
-
 Rattus norvegicus threo-(9R,10R)-dihydroxystearic acid methyl ester + threo-(9S,10S)-dihydroxystearic acid methyl ester enantioselective production of 79% (9R,10R)-diol and 21% (9S,10S)-diol ?
3.3.2.9 cis-(9R,10S)-epoxystearic acid methyl ester + H2O
-
 Zea mays threo-(9R,10R)-dihydroxystearic acid methyl ester + threo-(9S,10S)-dihydroxystearic acid methyl ester enantioselective production of 83% (9R,10R)-diol and 17% (9S,10S)-diol ?
3.3.2.9 cis-(9S,10R)-epoxystearic acid + H2O
-
 Rattus norvegicus threo-(9R,10R)-dihydroxystearic acid + threo-(9S,10S)-dihydroxystearic acid enantioselective production of 39% (9R,10R)-diol and 61% (9S,10S)-diol ?
3.3.2.9 cis-(9S,10R)-epoxystearic acid + H2O
-
 Zea mays threo-(9R,10R)-dihydroxystearic acid + threo-(9S,10S)-dihydroxystearic acid enantioselective production of 52% (9R,10R)-diol and 48% (9S,10S)-diol ?
3.3.2.9 cis-(9S,10R)-epoxystearic acid methyl ester + H2O
-
 Rattus norvegicus threo-(9R,10R)-dihydroxystearic acid methyl ester + threo-(9S,10S)-dihydroxystearic acid methyl ester enantioselective production of 48% (9R,10R)-diol and 52% (9S,10S)-diol ?
3.3.2.9 cis-(9S,10R)-epoxystearic acid methyl ester + H2O
-
 Zea mays threo-(9R,10R)-dihydroxystearic acid methyl ester + threo-(9S,10S)-dihydroxystearic acid methyl ester enantioselective production of 68% (9R,10R)-diol and 32% (9S,10S)-diol ?
3.3.2.9 additional information enantioselectivity with fatty acid epoxide substrates Rattus norvegicus ?
-
 ?
3.3.2.9 additional information enantioselectivity with fatty acid epoxide substrates Triticum aestivum ?
-
 ?
3.3.2.9 additional information enantioselectivity with fatty acid epoxide substrates Zea mays ?
-
 ?
3.3.2.9 additional information enantioselectivity with fatty acid epoxide substrates Solanum tuberosum ?
-
 ?
3.3.2.9 additional information enantioselectivity with fatty acid epoxide substrates Nicotiana tabacum ?
-
 ?
3.3.2.9 additional information enantioselectivity with fatty acid epoxide substrates Glycine max ?
-
 ?
3.3.2.9 additional information enantioselectivity with fatty acid epoxide substrates Apium graveolens ?
-
 ?
3.3.2.9 additional information enantioselectivity with fatty acid epoxide substrates Oryza sativa ?
-
 ?
3.3.2.9 additional information enantioselectivity with fatty acid epoxide substrates Musa x paradisiaca ?
-
 ?
3.3.2.9 racemic cis-9,10-epoxystearic acid + H2O 30% enantioselective (9S,10S)-cis-diol production Apium graveolens threo-(9R,10R)-dihydroxystearic acid + threo-(9S,10S)-dihydroxystearic acid
-
 ?
3.3.2.9 racemic cis-9,10-epoxystearic acid + H2O 59% enantioselective (9S,10S)-cis-diol production Triticum aestivum threo-(9R,10R)-dihydroxystearic acid + threo-(9S,10S)-dihydroxystearic acid
-
 ?
3.3.2.9 racemic cis-9,10-epoxystearic acid + H2O 63.5% enantioselective (9S,10S)-cis-diol production Musa x paradisiaca threo-(9R,10R)-dihydroxystearic acid + threo-(9S,10S)-dihydroxystearic acid
-
 ?
3.3.2.9 racemic cis-9,10-epoxystearic acid + H2O 74% enantioselective (9S,10S)-cis-diol production Oryza sativa threo-(9R,10R)-dihydroxystearic acid + threo-(9S,10S)-dihydroxystearic acid
-
 ?
3.3.2.9 racemic cis-9,10-epoxystearic acid + H2O 90% enantioselective (9S,10S)-cis-diol production by the constitutive enzyme, 86% by the pathogen-induced enzyme Solanum tuberosum threo-(9R,10R)-dihydroxystearic acid + threo-(9S,10S)-dihydroxystearic acid
-
 ?
3.3.2.9 racemic cis-9,10-epoxystearic acid + H2O 94% enantioselective (9S,10S)-cis-diol production Nicotiana tabacum threo-(9R,10R)-dihydroxystearic acid + threo-(9S,10S)-dihydroxystearic acid
-
 ?
3.3.2.9 racemic cis-9,10-epoxystearic acid + H2O 94% enantioselective (9S,10S)-cis-diol production Glycine max threo-(9R,10R)-dihydroxystearic acid + threo-(9S,10S)-dihydroxystearic acid
-
 ?
3.3.2.9 styrene oxide + H2O recombinant enzyme, low activity Glycine max 1-phenylethane-1,2-diol
-
 ?
3.3.2.10 cis-(9R,10S)-epoxystearic acid + H2O
-
 Rattus norvegicus threo-(9R,10R)-dihydroxystearic acid + threo-(9S,10S)-dihydroxystearic acid enantioselective, low production rate of the (9R,10R)-diol by wild-type and E404D mutant ?
3.3.2.10 cis-(9S,10R)-epoxystearic acid + H2O
-
 Rattus norvegicus threo-(9R,10R)-dihydroxystearic acid + threo-(9S,10S)-dihydroxystearic acid enantioselective, low production rate of the (9R,10R)-diol by wild-type and E404D mutant ?
3.3.2.10 additional information enantioselectivity with fatty acid epoxide substrates Rattus norvegicus ?
-
 ?

Subunits

EC Number Subunits Comment Organism
3.3.2.9 dimer mainly, in solution, recombinant enzyme, mass spectrometry Glycine max
3.3.2.9 More monomer or dimer Apium graveolens

Synonyms

EC Number Synonyms Comment Organism
3.3.2.9 More see also 3.1.3.76 Glycine max
3.3.2.9 SEH
-
 Rattus norvegicus
3.3.2.9 SEH
-
 Triticum aestivum
3.3.2.9 SEH
-
 Zea mays
3.3.2.9 SEH
-
 Solanum tuberosum
3.3.2.9 SEH
-
 Nicotiana tabacum
3.3.2.9 SEH
-
 Glycine max
3.3.2.9 SEH
-
 Apium graveolens
3.3.2.9 SEH
-
 Oryza sativa
3.3.2.9 SEH
-
 Musa x paradisiaca
3.3.2.10 mEH
-
 Rattus norvegicus

Temperature Optimum [°C]

EC Number Temperature Optimum [°C] Temperature Optimum Maximum [°C] Comment Organism
3.3.2.9 26
-
 assay at Rattus norvegicus
3.3.2.9 26
-
 assay at Triticum aestivum
3.3.2.9 26
-
 assay at Zea mays
3.3.2.9 26
-
 assay at Solanum tuberosum
3.3.2.9 26
-
 assay at Nicotiana tabacum
3.3.2.9 26
-
 assay at Glycine max
3.3.2.9 26
-
 assay at Apium graveolens
3.3.2.9 26
-
 assay at Oryza sativa
3.3.2.9 26
-
 assay at Musa x paradisiaca
3.3.2.10 26
-
 assay at Rattus norvegicus

pH Optimum

EC Number pH Optimum Minimum pH Optimum Maximum Comment Organism
3.3.2.9 5.5 8 broad maximum, recombinant enzyme Glycine max
3.3.2.9 7.4
-
 assay at Rattus norvegicus
3.3.2.9 7.4
-
 assay at Triticum aestivum
3.3.2.9 7.4
-
 assay at Zea mays
3.3.2.9 7.4
-
 assay at Solanum tuberosum
3.3.2.9 7.4
-
 assay at Nicotiana tabacum
3.3.2.9 7.4
-
 assay at Apium graveolens
3.3.2.9 7.4
-
 assay at Oryza sativa
3.3.2.9 7.4
-
 assay at Musa x paradisiaca
3.3.2.10 7.4
-
 assay at Rattus norvegicus