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IUBMB CommentsThe 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.
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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.
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(3R)-3,4-epoxy-3-methylbut-1-ene + glutathione
2-(glutathion-S-yl)-2-methylbut-3-en-1-ol
1,2-epoxybutane + glutathione
2-(glutathion-S-yl)-butan-1-ol
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
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
cis-2,3-epoxybutane + glutathione
3-(glutathion-S-yl)-butan-2-ol
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
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
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
28% of the activity with (3R)-3,4-epoxy-3-methylbut-1-ene
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-
?
epithiopropane + glutathione
2-(glutathion-S-yl)-propanthiol
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
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
trans-1,2-dichloroepoxyethane + glutathione
1,2-dichloro-2-(glutathion-S-yl)-ethan-1-ol
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-
-
?
(3R)-3,4-epoxy-3-methylbut-1-ene + glutathione
2-(glutathion-S-yl)-2-methylbut-3-en-1-ol
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-
?
(3R)-3,4-epoxy-3-methylbut-1-ene + glutathione
2-(glutathion-S-yl)-2-methylbut-3-en-1-ol
i.e. isoprene monoxide. Nucleophilic attack of GSH occurs on the tertiary carbon atom of the epoxide ring
i.e. 1-hydroxy-2-glutathionyl-2-methyl-3-butene
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?
cis-1,2-dichloroepoxyethane + glutathione
1,2-dichloro-2-(glutathion-S-yl)-ethan-1-ol
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-
-
?
cis-1,2-dichloroepoxyethane + glutathione
1,2-dichloro-2-(glutathion-S-yl)-ethan-1-ol
4% 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
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-
-
?
epoxypropane + glutathione
2-(glutathion-S-yl)-propan-1-ol
32% of the activity with (3R)-3,4-epoxy-3-methylbut-1-ene
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-
?
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(3R)-3,4-epoxy-3-methylbut-1-ene + glutathione
2-(glutathion-S-yl)-2-methylbut-3-en-1-ol
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-
-
?
cis-1,2-dichloroepoxyethane + glutathione
1,2-dichloro-2-(glutathion-S-yl)-ethan-1-ol
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-
-
?
epoxypropane + glutathione
2-(glutathion-S-yl)-propan-1-ol
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-
-
?
trans-1,2-dichloroepoxyethane + glutathione
1,2-dichloro-2-(glutathion-S-yl)-ethan-1-ol
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?
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1,2-Epoxybutane
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
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
additional information
not inhibitory: 1 mM MnCl2, CoCl2, CuSO4, MgSO4, RbCl2, or ZnSO4
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Van Hylckama Vlieg, J.; Kingma, J.; Van Den Wijngaard, A.; Janssen, D.
A glutathione S-transferase with activity towards cis-1,2-dichloroepoxyethane is involved in isoprene utilization by Rhodococcus sp. strain AD45
Appl. Environ. Microbiol.
64
2800-2805
1998
Rhodococcus sp. (Q9RBP4)
brenda
Van Hylckama Vlieg, J.; Kingma, J.; Kruizinga, W.; Janssen, D.
Purification of a glutathione S-transferase and a glutathione conjugate-specific dehydrogenase involved in isoprene metabolism in Rhodococcus sp. strain AD45
J. Bacteriol.
181
2094-2101
1999
Rhodococcus sp. (Q9RBP4)
brenda