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IUBMB Comments The enzyme acts in the degradation pathway of unsaturated organohalogen compounds by the bacterium Burkholderia sp. WS.
Synonyms
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(S)-2-chloropropanoate + NADP+ = 2-chloroacrylate + NADPH + H+
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MetaCyc
2-chloroacrylate degradation I
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(S)-2-chloropropanoate:NADP+ oxidoreductase
The enzyme acts in the degradation pathway of unsaturated organohalogen compounds by the bacterium Burkholderia sp. WS.
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2-bromoacrylate + NADPH + H+
(S)-2-bromopropanoate + NADP+
Substrates: no activity with NADH
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2-chloroacrylate + NADPH + H+
(S)-2-chloropropanoate + NADP+
additional information
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Substrates: no activity with 1,4-benzoquinone, 1,4-naphthoquinone, acrylate and methacrylate
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2-chloroacrylate + NADPH + H+
(S)-2-chloropropanoate + NADP+
Substrates: -
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2-chloroacrylate + NADPH + H+
(S)-2-chloropropanoate + NADP+
Substrates: no activity with NADH
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2-chloroacrylate + NADPH + H+
(S)-2-chloropropanoate + NADP+
Substrates: the enzyme is involved in the degradation of unsaturated organohalogen compounds
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2-bromoacrylate + NADPH + H+
(S)-2-bromopropanoate + NADP+
Substrates: no activity with NADH
?
2-chloroacrylate + NADPH + H+
(S)-2-chloropropanoate + NADP+
2-chloroacrylate + NADPH + H+
(S)-2-chloropropanoate + NADP+
Substrates: -
?
2-chloroacrylate + NADPH + H+
(S)-2-chloropropanoate + NADP+
Substrates: the enzyme is involved in the degradation of unsaturated organohalogen compounds
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NADPH
no activity with NADH
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2-bromoacrylate
above 2.5 mM
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0.19
2-bromoacrylate
pH 8.0, 35°C
0.45
2-chloroacrylate
pH 8.0, 35°C
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1.9
2-chloroacrylate, pH 8.0, 35°C
2.8
2-bromoacrylate, pH 8.0, 35°C
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UniProt
brenda
Highest Expressing Human Cell Lines
Filter by:
Cell Line Links
Gene Links
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35656
1 * 35656, calculated from sequence
35660
mass spectrometric analysis
37000
1 * 37000, SDS-PAGE
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monomer
1 * 37000, SDS-PAGE
monomer
1 * 35656, calculated from sequence
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7 - 8
30°C, 30 min
722645
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expression in Escherichia coli
overproduced in Escherichia coli
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analysis
monitoring the production of (S)-2-chloropropionate from 2-chloroacrylate as a model system for monitoring NADPH availability. A phosphofructokinase pfkA pfkB double-deletion strain shows the highest yield of 2-chloropropionic acid product. The flux distribution of fructose-6-phosphate between glycolysis and the pentose phosphate pathway determines the amount of NAPDH available for reductive biosynthesis
analysis
monitoring the production of (S)-2-chloropropionate from 2-chloroacrylate as a model system for monitoring NADPH availability. The presence of transhydrogenase UdhA increases product yield and NADPH availability while the presence of transhydrogenase PntAB has the opposite effect. A maximum product yield of 1.4 mol product/mol glucose is achieved aerobically in a Pnt-deletion strain with UdhA overexpression, a 150% improvement over the wild-type strain
synthesis
construction of a system for asymmetric reduction of 2-chloroacrylate to produce (S)-2-chloropropionate with recombinant Escherichia coli cells producing 2-haloacrylate reductase from Burkholderia sp. WS and an NADPH regeneration system. The system provided 37.4 g/l (S)-2-chloropropionate in more than 99.9%e.e. (S)-2-Chloropropionate is a synthetic intermediate for phenoxypropionic acid herbicides
synthesis
the enzyme is useful for the production of (S)-2-chloropropionate, which is used for the industrial production of aryloxyphenoxypropionic acid herbicides
synthesis
the enzyme is useful in the production of L-2-chloropropionate, a building block in the synthesis of aryloxyphenoxypropionate herbicides
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Kurihara, T.
A mechanistic analysis of enzymatic degradation of organohalogen compounds
Biosci. Biotechnol. Biochem.
75
189-198
2011
Burkholderia sp. (Q59I44)
brenda
Kurata, A.; Kurihara, T.; Kamachi, H.; Esaki N.
2-Haloacrylate reductase, a novel enzyme of the medium chain dehydrogenase/reductase superfamily that catalyzes the reduction of a carbon-carbon double bond of unsaturated organohalogen compounds
J. Biol. Chem.
280
20286-20291
2005
Burkholderia sp. (Q59I44)
brenda
Kurata, A.; Fujita, M.; Mowafy, A.M.; Kamachi, H.; Kurihara, T.; Esaki, N.
Production of (S)-2-chloropropionate by asymmetric reduction of 2-chloroacrylate with 2-haloacrylate reductase coupled with glucose dehydrogenase
J. Biosci. Bioeng.
105
429-431
2008
Burkholderia sp. (Q59I44)
brenda
Jan, J.; Martinez, I.; Wang, Y.; Bennett, G.; San, K.
Metabolic engineering and transhydrogenase effects on NADPH availability in Escherichia coli
Biotechnol. Prog.
29
1124-1130
2013
Burkholderia sp. (Q59I44)
brenda
Wang, Y.; San, K.Y.; Bennett, G.N.
Improvement of NADPH bioavailability in Escherichia coli by replacing NAD+-dependent glyceraldehyde-3-phosphate dehydrogenase GapA with NADP+-dependent GapB from Bacillus subtilis and addition of NAD kinase
J. Ind. Microbiol. Biotechnol.
40
1449-1460
2013
Burkholderia sp. (Q59I44)
brenda
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