Information on EC 4.4.1.34 - isoprene-epoxide-glutathione S-transferase

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The expected taxonomic range for this enzyme is: Rhodococcus sp.

EC NUMBER
COMMENTARY hide
4.4.1.34
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RECOMMENDED NAME
GeneOntology No.
isoprene-epoxide-glutathione S-transferase
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REACTION
REACTION DIAGRAM
COMMENTARY hide
ORGANISM
UNIPROT
LITERATURE
2-(glutathion-S-yl)-2-methylbut-3-en-1-ol = (3R)-3,4-epoxy-3-methylbut-1-ene + glutathione
show the reaction diagram
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-
-
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PATHWAY
BRENDA Link
KEGG Link
MetaCyc Link
isoprene degradation
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SYSTEMATIC NAME
IUBMB Comments
2-(glutathion-S-yl)-2-methylbut-3-en-1-ol lyase [(3R)-3,4-epoxy-3-methylbut-1-ene forming]
The enzyme, characterized from the bacterium Rhodococcus sp. AD45, is involved in isoprene degradation. The enzyme can catalyse the glutathione-dependent ring opening of various epoxides, but the highest activity is with (3R)-3,4-epoxy-3-methylbut-1-ene, which is derived from isoprene by EC 1.14.13.69, alkene monooxygenase.
ORGANISM
COMMENTARY hide
LITERATURE
UNIPROT
SEQUENCE DB
SOURCE
GENERAL INFORMATION
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
physiological function
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the enzyme is a glutathione S-transferase involved in the metabolism of isoprene and able to detoxify reactive epoxides produced by monooxygenation of chlorinated ethenes
SUBSTRATE
PRODUCT                       
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate) hide
LITERATURE
(Substrate)
COMMENTARY
(Product) hide
LITERATURE
(Product)
Reversibility
r=reversible
ir=irreversible
?=not specified
(3R)-3,4-epoxy-3-methylbut-1-ene + glutathione
2-(glutathion-S-yl)-2-methylbut-3-en-1-ol
show the reaction diagram
1,2-epoxybutane + glutathione
2-(glutathion-S-yl)-butan-1-ol
show the reaction diagram
26% of the activity with (3R)-3,4-epoxy-3-methylbut-1-ene
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-
?
1,2-epoxyhexane + glutathione
2-(glutathion-S-yl)-hexan-1-ol
show the reaction diagram
25% of the activity with (3R)-3,4-epoxy-3-methylbut-1-ene
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-
?
cis-1,2-dichloroepoxyethane + glutathione
1,2-dichloro-2-(glutathion-S-yl)-ethan-1-ol
show the reaction diagram
cis-2,3-epoxybutane + glutathione
3-(glutathion-S-yl)-butan-2-ol
show the reaction diagram
13% of the activity with (3R)-3,4-epoxy-3-methylbut-1-ene
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-
?
epibromohydrin + glutathione
3-bromo-2-(glutathion-S-yl)-propan-1-ol
show the reaction diagram
25% of the activity with (3R)-3,4-epoxy-3-methylbut-1-ene
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-
?
epichlorohydrin + glutathione
3-chloro-2-(glutathion-S-yl)-propan-1-ol
show the reaction diagram
31% of the activity with (3R)-3,4-epoxy-3-methylbut-1-ene
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-
?
epifluorohydrin + glutathione
3-fluoro-2-(glutathion-S-yl)-propan-1-ol
show the reaction diagram
28% of the activity with (3R)-3,4-epoxy-3-methylbut-1-ene
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-
?
epithiopropane + glutathione
2-(glutathion-S-yl)-propanthiol
show the reaction diagram
34% of the activity with (3R)-3,4-epoxy-3-methylbut-1-ene
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-
?
epoxyethane + glutathione
2-(glutathion-S-yl)-ethan-1-ol
show the reaction diagram
37% of the activity with (3R)-3,4-epoxy-3-methylbut-1-ene
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-
?
epoxypropane + glutathione
2-(glutathion-S-yl)-propan-1-ol
show the reaction diagram
trans-1,2-dichloroepoxyethane + glutathione
1,2-dichloro-2-(glutathion-S-yl)-ethan-1-ol
show the reaction diagram
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-
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-
?
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
(3R)-3,4-epoxy-3-methylbut-1-ene + glutathione
2-(glutathion-S-yl)-2-methylbut-3-en-1-ol
show the reaction diagram
-
-
-
-
?
cis-1,2-dichloroepoxyethane + glutathione
1,2-dichloro-2-(glutathion-S-yl)-ethan-1-ol
show the reaction diagram
-
-
-
-
?
epoxypropane + glutathione
2-(glutathion-S-yl)-propan-1-ol
show the reaction diagram
-
-
-
-
?
trans-1,2-dichloroepoxyethane + glutathione
1,2-dichloro-2-(glutathion-S-yl)-ethan-1-ol
show the reaction diagram
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-
-
-
?
INHIBITORS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
1,2-Epoxybutane
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addition of low concentrations of 1,2-epoxybutane and 1,2-epoxyhexane strongly inhibits growth on isoprene but not growth on ethanol and irreversibly inhibits the epoxide-degrading activity
1,2-epoxyhexane
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addition of low concentrations of 1,2-epoxybutane and 1,2-epoxyhexane strongly inhibits growth on isoprene but not growth on ethanol and irreversibly inhibits the epoxide-degrading activity
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additional information
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not inhibitory: 1 mM MnCl2, CoCl2, CuSO4, MgSO4, RbCl2, or ZnSO4
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KM VALUE [mM]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.3
(3R)-3,4-epoxy-3-methylbut-1-ene
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pH 8.5, 30C
0.1
cis-1,2-dichloroepoxyethane
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pH 8.5, 30C
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MOLECULAR WEIGHT
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
46000
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gel filtration
SUBUNITS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
dimer
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2 * 27000, SDS-PAGE
STORAGE STABILITY
ORGANISM
UNIPROT
LITERATURE
4C or -20C, storable for 3 months with less than 20% loss of activity
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APPLICATION
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
degradation
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enzyme is involved in degradation of primary oxidation products of isoprene, cis-1,2-dichloroethanol, and trans-1,2-dichloroethanol