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Information on EC 5.3.99.7 - styrene-oxide isomerase
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5.3.99.7 styrene-oxide isomeraseIUBMB Comments
Highly specific.
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Word Map
- 5.3.99.7
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silicon-on-insulator
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fabric
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silicon
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waveguide
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photon
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wafer
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grate
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coupler
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grating
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spin-orbit
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bandwidth
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etch
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homeless
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semiconductor
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lithography
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nanowire
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mach-zehnder
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transistor
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bragg
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interferometer
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on-chip
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toronto
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nanophotonic
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reflector
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adiabatic
- phenylacetaldehyde
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metal-oxide-semiconductor
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photodetectors
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splitter
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microring
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clad
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single-mode
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field-effect
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heater
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foundry
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telecommunication
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heterostructures
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low-loss
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germanium
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all-optical
The enzyme appears in viruses and cellular organisms
Synonyms
soi, styrene oxide isomerase, 
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SYNONYM 
ORGANISM
UNIPROT
COMMENTARY 
LITERATURE
isomerase, styrene oxide
-
-
-
-
SOI
SOOI
StyC
styrene oxide isomerase
SOI
-
-
-
-
styrene oxide isomerase
-
-
-
-
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REACTION
REACTION DIAGRAM
COMMENTARY
ORGANISM
UNIPROT
LITERATURE
styrene oxide = phenylacetaldehyde
-
-
-
-
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REACTION TYPE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
intramolecular oxidoreduction
-
-
-
-
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PATHWAY SOURCE
PATHWAYS
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SYSTEMATIC NAME
IUBMB Comments
styrene-oxide isomerase (epoxide-cleaving)
Highly specific.
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CAS REGISTRY NUMBER
COMMENTARY
124541-89-5
-
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SUBSTRATE
PRODUCT
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate)
(Substrate)
LITERATURE
(Substrate)
(Substrate)
COMMENTARY
(Product)
(Product)
LITERATURE
(Product)
(Product)
Reversibility
r=reversible
ir=irreversible
?=not specified
r=reversible
ir=irreversible
?=not specified
(R,S)-4-chlorostyrene oxide
4-chlorophenylacetaldehyde
-
low activity
-
-
?
6,6a-dihydro-1aH-indeno[1,2-b]oxirene
1,3-dihydro-2H-inden-2-one
-
45% of the activity with 2-phenyloxirane
-
-
?
(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)-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
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3.7% of the activity with 2-phenyloxirane
-
-
?
2-(4-chlorophenyl)oxirane
(4-chlorophenyl)acetaldehyde
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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
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15% of the activity with 2-phenyloxirane
-
-
?
styrene oxide + H2O
phenylacetaldehyde
aerobic bacterium (strain S5)
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enzyme is involved in the pathway of styrene degradation
-
?
styrene oxide + H2O
phenylacetaldehyde
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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
-
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
-
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
-
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
-
equilibrium constant favors phenylacetaldehyde formation
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r
styrene oxide + H2O
phenylacetaldehyde
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equilibrium constant favors phenylacetaldehyde formation
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r
additional information
?
-
-
the enzyme shows the ability to convert a spectrum of substituted styrene oxides
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-
?
additional information
?
-
-
the enzyme shows the ability to convert a spectrum of substituted styrene oxides
-
-
?
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NATURAL SUBSTRATE
NATURAL PRODUCT
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate)
(Substrate)
LITERATURE
(Substrate)
(Substrate)
COMMENTARY
(Product)
(Product)
LITERATURE
(Product)
(Product)
REVERSIBILITY
r=reversible
ir=irreversible
?=not specified
r=reversible
ir=irreversible
?=not specified
styrene oxide + H2O
phenylacetaldehyde
aerobic bacterium (strain S5)
-
enzyme is involved in the pathway of styrene degradation
-
?
styrene oxide + H2O
phenylacetaldehyde
-
key enzyme of styrene and styrene oxide metabolism
-
-
ir
styrene oxide + H2O
phenylacetaldehyde
-
key enzyme of styrene and styrene oxide metabolism
-
-
ir
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
-
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
-
-
?
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METALS and IONS
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
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INHIBITOR
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
phenylacetaldehyde
-
irreversible product inhibition, half-life of 15 min determined at a phenylacetaldehyde concentration of about 55 mM
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KM VALUE [mM]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
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SPECIFIC ACTIVITY [µmol/min/mg]
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
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pH OPTIMUM
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
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pH RANGE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
5 - 10
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pH 5.0-7.5: maximal activity, pH 10.0: about 50% of maximal activity
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TEMPERATURE OPTIMUM
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
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TEMPERATURE RANGE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
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ORGANISM
COMMENTARY
LITERATURE
UNIPROT
SEQUENCE DB
SOURCE
gene styC, strain ST-5 has a gene cluster containing four open reading frames which encode styrene degradation enzymes
UniProt
brenda
gene styC, strain ST-5 has a gene cluster containing four open reading frames which encode styrene degradation enzymes
UniProt
brenda
strain AC-5 and strain ST-5. Strain ST-10 does not have a styrene oxide isoemrase and metabolized styrene oxide by an unknown enzymatic reaction
-
-
brenda
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SOURCE TISSUE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
SOURCE
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LOCALIZATION
ORGANISM
UNIPROT
COMMENTARY
GeneOntology No.
LITERATURE
SOURCE
additional information
additional information
-
not membrane-bound, probably bound to the cell wall
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brenda
additional information
-
not membrane-bound, probably bound to the cell wall
-
-
brenda
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GENERAL INFORMATION
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
metabolism
additional information
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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UNIPROT
ENTRY NAME
ORGANISM
NO. OF AA
NO. OF TRANSM. HELICES
MOLECULAR WEIGHT[Da]
SOURCE
SEQUENCE
LOCALIZATION PREDICTION
The reliability class of the localization prediction ranges from 1 (very reliable) to 5 (not reliable).
The reliability class of the localization prediction ranges from 1 (very reliable) to 5 (not reliable). A0A6P2HNG6_BURL3
Burkholderia lata (strain ATCC 17760 / DSM 23089 / LMG 22485 / NCIMB 9086 / R18194 / 383)
153
3
16697
TrEMBL
-
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PROTEIN VARIANTS
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
additional information
additional information
-
enzyme disruption mutant is unable to grow on styrene or styrene oxide and accumulates enantiopure (S)-styrene when incubated with styrene. Upon growth on citrate as carbon source, mutant strain exhibits a high whole-cell activity of styrene oxide formation
additional information
-
enzyme disruption mutant is unable to grow on styrene or styrene oxide and accumulates enantiopure (S)-styrene when incubated with styrene. Upon growth on citrate as carbon source, mutant strain exhibits a high whole-cell activity of styrene oxide formation
-
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pH STABILITY
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
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TEMPERATURE STABILITY
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
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STORAGE STABILITY
ORGANISM
UNIPROT
LITERATURE
4°C, 50 mM potassium phosphate buffer, pH 7.0, 30% loss of activity after 2 weeks
-
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PURIFICATION (Commentary)
ORGANISM
UNIPROT
LITERATURE
native enzyme partially from styrene-grown cells by membrane preparation and solubilization
-
partial purification
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CLONED (Commentary)
ORGANISM
UNIPROT
LITERATURE
expressed in Escherichia coli BL21(DE3) cells
gene styC, DNA and amino acid sequence determination and analysis, genetic organization, expression in Escherichia coli
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EXPRESSION
ORGANISM
UNIPROT
LITERATURE
the enzyme is strongly induced by styrene, to a lesser extent by styrene oxide and phenylacetaldehyde, no induction by phenylacetic acid or glucose
the enzyme is strongly induced by styrene, to a lesser extent by styrene oxide and phenylacetaldehyde, no induction by phenylacetic acid or glucose
-
the enzyme is strongly induced by styrene, to a lesser extent by styrene oxide and phenylacetaldehyde, no induction by phenylacetic acid or glucose
-
-
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APPLICATION
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
synthesis
synthesis
-
the highly stereospecific enzyme can be used in a biotransformation system producing (R)-styrene oxide
synthesis
-
enzyme disruption mutant is unable to grow on styrene or styrene oxide and accumulates enantiopure (S)-styrene when incubated with styrene. Upon growth on citrate as carbon source, mutant strain exhibits a high whole-cell activity of styrene oxide formation. In a 3 l bioreactor experiment, mutant can accumulate 150 mM (S)-styrene oxide at an enantiomerixc excess above 98% in 13 h
synthesis
-
enzyme disruption mutant is unable to grow on styrene or styrene oxide and accumulates enantiopure (S)-styrene when incubated with styrene. Upon growth on citrate as carbon source, mutant strain exhibits a high whole-cell activity of styrene oxide formation. In a 3 l bioreactor experiment, mutant can accumulate 150 mM (S)-styrene oxide at an enantiomerixc excess above 98% in 13 h
-
synthesis
-
the highly stereospecific enzyme can be used in a biotransformation system producing (R)-styrene oxide
-
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REF.
AUTHORS
TITLE
JOURNAL
VOL.
PAGES
YEAR
ORGANISM (UNIPROT)
PUBMED ID
SOURCE
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
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