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(R)-styrene oxide
phenylacetaldehyde
(R,S)-3-chlorostyrene oxide
3-chlorophenylacetaldehyde
(R,S)-4-bromostyrene oxide
4-bromophenylacetaldehyde
(R,S)-4-chlorostyrene oxide
4-chlorophenylacetaldehyde
-
low activity
-
-
?
(R,S)-4-fluorostyrene oxide
4-fluorophenylacetaldehyde
-
-
-
-
?
(R,S)-4-methylstyrene oxide
4-methylphenylacetaldehyde
-
-
-
-
?
(R,S)-styrene oxide
phenylacetaldehyde
-
best substrate
-
-
?
(S)-styrene oxide
phenylacetaldehyde
-
best substrate
-
-
?
1a,2,3,7b-tetrahydronaphtho[1,2-b]oxirene
3,4-dihydronaphthalen-2(1H)-one
2-(4-chlorophenyl)oxirane
(4-chlorophenyl)acetaldehyde
2-(4-methylphenyl)oxirane
(4-methylphenyl)acetaldehyde
2-ethyl-2-phenyloxirane
2-phenylbutanal
2-methyl-2-phenyloxirane
hydratropaldehyde
2-phenyloxirane
phenylacetaldehyde
-
-
-
-
?
6,6a-dihydro-1aH-indeno[1,2-b]oxirene
1,3-dihydro-2H-inden-2-one
-
45% of the activity with 2-phenyloxirane
-
-
?
styrene oxide
phenylacetaldehyde
styrene oxide + H2O
phenylacetaldehyde
additional information
?
-
(R)-styrene oxide
phenylacetaldehyde
-
45% of activity compared to (S)-styrene oxide and (R,S)-styrene oxide
-
-
?
(R)-styrene oxide
phenylacetaldehyde
-
45% of activity compared to (S)-styrene oxide and (R,S)-styrene oxide
-
-
?
(R,S)-3-chlorostyrene oxide
3-chlorophenylacetaldehyde
-
-
-
-
?
(R,S)-3-chlorostyrene oxide
3-chlorophenylacetaldehyde
-
-
-
-
?
(R,S)-4-bromostyrene oxide
4-bromophenylacetaldehyde
-
low activity
-
-
?
(R,S)-4-bromostyrene oxide
4-bromophenylacetaldehyde
-
low activity
-
-
?
1a,2,3,7b-tetrahydronaphtho[1,2-b]oxirene
3,4-dihydronaphthalen-2(1H)-one
-
0.5% of the activity with 2-phenyloxirane
-
-
?
1a,2,3,7b-tetrahydronaphtho[1,2-b]oxirene
3,4-dihydronaphthalen-2(1H)-one
-
0.5% of the activity with 2-phenyloxirane
-
-
?
2-(4-chlorophenyl)oxirane
(4-chlorophenyl)acetaldehyde
-
3.7% of the activity with 2-phenyloxirane
-
-
?
2-(4-chlorophenyl)oxirane
(4-chlorophenyl)acetaldehyde
-
3.7% of the activity with 2-phenyloxirane
-
-
?
2-(4-methylphenyl)oxirane
(4-methylphenyl)acetaldehyde
-
113% of the activity with 2-phenyloxirane
-
-
?
2-(4-methylphenyl)oxirane
(4-methylphenyl)acetaldehyde
-
113% of the activity with 2-phenyloxirane
-
-
?
2-ethyl-2-phenyloxirane
2-phenylbutanal
-
7.6% of the activity with 2-phenyloxirane
-
-
?
2-ethyl-2-phenyloxirane
2-phenylbutanal
-
7.6% of the activity with 2-phenyloxirane
-
-
?
2-methyl-2-phenyloxirane
hydratropaldehyde
-
15% of the activity with 2-phenyloxirane
-
-
?
2-methyl-2-phenyloxirane
hydratropaldehyde
-
15% of the activity with 2-phenyloxirane
-
-
?
styrene oxide
phenylacetaldehyde
-
-
-
?
styrene oxide
phenylacetaldehyde
-
-
-
?
styrene oxide
phenylacetaldehyde
-
-
-
-
?
styrene oxide
phenylacetaldehyde
-
-
-
?
styrene oxide
phenylacetaldehyde
-
-
-
-
?
styrene oxide
phenylacetaldehyde
-
-
-
?
styrene oxide
phenylacetaldehyde
-
-
-
?
styrene oxide
phenylacetaldehyde
-
-
-
?
styrene oxide
phenylacetaldehyde
-
-
-
?
styrene oxide
phenylacetaldehyde
-
-
-
?
styrene oxide + H2O
phenylacetaldehyde
aerobic bacterium (strain S5)
-
-
-
?
styrene oxide + H2O
phenylacetaldehyde
aerobic bacterium (strain S5)
-
enzyme is involved in the pathway of styrene degradation
-
?
styrene oxide + H2O
phenylacetaldehyde
-
-
-
?
styrene oxide + H2O
phenylacetaldehyde
-
compared with the (R)-isomer, the relative activity of the enzyme towards (R)-styrene oxide is 51% of that for the (S)-isomer
-
-
?
styrene oxide + H2O
phenylacetaldehyde
-
key enzyme of styrene and styrene oxide metabolism
-
-
ir
styrene oxide + H2O
phenylacetaldehyde
-
-
-
?
styrene oxide + H2O
phenylacetaldehyde
-
compared with the (R)-isomer, the relative activity of the enzyme towards (R)-styrene oxide is 51% of that for the (S)-isomer
-
-
?
styrene oxide + H2O
phenylacetaldehyde
-
key enzyme of styrene and styrene oxide metabolism
-
-
ir
styrene oxide + H2O
phenylacetaldehyde
-
-
-
?
styrene oxide + H2O
phenylacetaldehyde
-
-
-
-
?
styrene oxide + H2O
phenylacetaldehyde
-
enzyme is involved in the pathway of styrene degradation
-
?
styrene oxide + H2O
phenylacetaldehyde
-
styrene, styrene oxide, and phenylacetaldehyde induce the enzymes involved in the degradation of styrene to phenylacetic acid, glucose has no effect
-
-
?
styrene oxide + H2O
phenylacetaldehyde
-
-
-
?
styrene oxide + H2O
phenylacetaldehyde
-
enzyme is involved in the pathway of styrene degradation
-
?
styrene oxide + H2O
phenylacetaldehyde
-
-
-
-
?
styrene oxide + H2O
phenylacetaldehyde
-
styrene, styrene oxide, and phenylacetaldehyde induce the enzymes involved in the degradation of styrene to phenylacetic acid, glucose has no effect
-
-
?
styrene oxide + H2O
phenylacetaldehyde
-
equilibrium constant favors phenylacetaldehyde formation
-
r
styrene oxide + H2O
phenylacetaldehyde
-
equilibrium constant favors phenylacetaldehyde formation
-
r
additional information
?
-
-
the enzyme shows the ability to convert a spectrum of substituted styrene oxides
-
-
?
additional information
?
-
-
the enzyme shows the ability to convert a spectrum of substituted styrene oxides
-
-
?
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metabolism
the enzyme is involved in the styrene degradation pathway, overview
metabolism
-
the enzyme is part of the upper pathway of styrene degradation via side chain oxygenation
metabolism
-
the enzyme is involved in the styrene degradation pathway, overview
-
metabolism
-
the enzyme is part of the upper pathway of styrene degradation via side chain oxygenation
-
additional information
in strain ST-10, which lacks a styrene oxide isomerase, styrene oxide is converted to phenylacetaldehyde by spontaneous chemical reaction. The strain accumulates styrene oxide as a metabolic intermediate. The produced phenylacetaldehyde is converted to phenylacetic acid in strain ST-10 as well as in strain ST-5
additional information
-
in strain ST-10, which lacks a styrene oxide isomerase, styrene oxide is converted to phenylacetaldehyde by spontaneous chemical reaction. The strain accumulates styrene oxide as a metabolic intermediate. The produced phenylacetaldehyde is converted to phenylacetic acid in strain ST-10 as well as in strain ST-5
additional information
-
in strain ST-10, which lacks a styrene oxide isomerase, styrene oxide is converted to phenylacetaldehyde by spontaneous chemical reaction. The strain accumulates styrene oxide as a metabolic intermediate. The produced phenylacetaldehyde is converted to phenylacetic acid in strain ST-10 as well as in strain ST-5
-
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Hartmans, S.; van der Werf, M.J.; de Bont, J.A.M.
Bacterial degradation of styrene involving a novel flavin adenine dinucleotide-dependent styrene monooxygenase
Appl. Environ. Microbiol.
56
1347-1351
1990
aerobic bacterium (strain S5)
brenda
Hartmans, S.; Smits, J.P.; van der Werf, M.J.; Volkering, F.; de Bont, J.A.M.
Metabolism of styrene oxide and 2-phenylethanol in the styrene-degrading Xanthobacter strain 124X
Appl. Environ. Microbiol.
55
2850-2855
1989
Xanthobacter sp., Xanthobacter sp. 124X
brenda
O'Connor, K.; Duetz, W.; Wind, B.; Dobson, A.D.W.
The effect of nutrient limitation on styrene metabolism in Pseudomonas putida CA-3
Appl. Environ. Microbiol.
62
3594-3599
1996
Pseudomonas putida, Pseudomonas putida CA-3
brenda
Itoh, N.; Yoshida, K.; Okada, K.
Isolation and identification of styrene-degrading Corynebacterium strains, and their styrene metabolism
Biosci. Biotechnol. Biochem.
60
1826-1830
1996
Corynebacterium sp., Corynebacterium sp. AC-5
brenda
O'Connor, K.; Buckley, C.M.; Hartmans, S.; Dobson, A.D.W.
Possible regulatory role for nonaromatic carbon sources in styrene degradation by Pseudomonas putida CA-3
Appl. Environ. Microbiol.
61
544-548
1995
Pseudomonas putida, Pseudomonas putida CA-3
brenda
Itoh, N.; Hayashi, K.; Okada, K.; Ito, T.; Mizuguchi, N.
Characterization of Styrene Oxide Isomerase, a Key Enzyme of Styrene and Styrene Oxide Metabolism in Corynehacterium sp.
Biosci. Biotechnol. Biochem.
61
2058-2062
1997
Corynebacterium sp., Pseudomonas sp., Pseudomonas sp. SK3, Corynebacterium sp. AC-5
brenda
Han, J.H.; Park, M.S.; Bae, J.W.; Lee, E.Y.; Yoon, Y.J.; Lee, S.; Park, S.
Production of (S)-styrene oxide using styrene oxide isomerase negative mutant of Pseudomonas putida SN1
Enzyme Microb. Technol.
39
1264-1269
2006
Pseudomonas putida, Pseudomonas putida SN1
-
brenda
Miyamoto, K.; Okuro, K.; Ohta, H.
Substrate specificity and reaction mechanism of recombinant styrene oxide isomerase from Pseudomonas putida S12
Tetrahedron Lett.
48
3255-3257
2007
Pseudomonas putida, Pseudomonas putida S12
-
brenda
Oelschlaegel, M.; Groening, J.A.; Tischler, D.; Kaschabek, S.R.; Schloemann, M.
Styrene oxide isomerase of Rhodococcus opacus 1CP, a highly stable and considerably active enzyme
Appl. Environ. Microbiol.
78
4330-4337
2012
Rhodococcus opacus, Rhodococcus opacus 1CP
brenda
Toda, H.; Itoh, N.
Isolation and characterization of styrene metabolism genes from styrene-assimilating soil bacteria Rhodococcus sp. ST-5 and ST-10
J. Biosci. Bioeng.
113
12-19
2012
no activity in Rhodococcus sp. ST-10, Rhodococcus sp. (G3XEX7), Rhodococcus sp., Rhodococcus sp. ST-5 (G3XEX7)
brenda
Oelschlaegel, M.; Richter, L.; Stuhr, A.; Hofmann, S.; Schloemann, M.
Heterologous production of different styrene oxide isomerases for the highly efficient synthesis of phenylacetaldehyde
J. Biotechnol.
252
43-49
2017
Rhodococcus opacus (A0A076JZU4), Sphingopyxis fribergensis (A0A076K0M9), Sphingopyxis fribergensis, Pseudomonas fluorescens (O06836), Rhodococcus opacus 1CP (A0A076JZU4), Rhodococcus opacus 1CP, Pseudomonas fluorescens ST (O06836), Pseudomonas fluorescens ST, Sphingopyxis fribergensis Kp5.2 (A0A076K0M9)
brenda