Information on EC 1.3.1.102 - 2-alkenal reductase (NADP+)

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The enzyme appears in viruses and cellular organisms

EC NUMBER
COMMENTARY hide
1.3.1.102
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RECOMMENDED NAME
GeneOntology No.
2-alkenal reductase (NADP+)
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REACTION
REACTION DIAGRAM
COMMENTARY hide
ORGANISM
UNIPROT
LITERATURE
an n-alkanal + NADP+ = an alk-2-enal + NADPH + H+
show the reaction diagram
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-
-
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SYSTEMATIC NAME
IUBMB Comments
n-alkanal:NADP+ 2-oxidoreductase
Shows highest activity with 1-nitrocyclohexene but also has significant activity with 2-methylpentenal and trans-cinnamaldehyde [3]. Involved in the detoxication of alpha,beta-unsaturated aldehydes and ketones. Has very low activity with NAD as reductant (cf. EC 1.3.1.74, 2-alkenal reductase [NAD(P)+]).
ORGANISM
COMMENTARY hide
LITERATURE
UNIPROT
SEQUENCE DB
SOURCE
-
-
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Manually annotated by BRENDA team
SUBSTRATE
PRODUCT                       
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate) hide
LITERATURE
(Substrate)
COMMENTARY
(Product) hide
LITERATURE
(Product)
Reversibility
r=reversible
ir=irreversible
?=not specified
(1R,2S,4S)-neoisodihydrocarveol + NADP+
(1R,4S)-isodihydrocarvone + NADPH + H+
show the reaction diagram
-
-
-
r
(2E)-3-methylpent-2-enal + NADPH + H+
2-methylpentanal + NADP+
show the reaction diagram
-
-
-
-
?
(2R,4R)-carveol + NADP+
(R)-carvone + NADPH + H+
show the reaction diagram
-
-
-
r
(2R,4S)-carveol + NADP+
(S)-carvone + NADPH + H+
show the reaction diagram
-
-
-
r
(2S,4R)-carveol + NADP+
(R)-carvone + NADPH + H+
show the reaction diagram
-
-
-
r
(2S,4S)-carveol + NADP+
(S)-carvone + NADPH + H+
show the reaction diagram
-
-
-
r
(R)-pulegone + NADPH + H+
(1R,4R)-isomenthone + (1R,4S)-menthone + NADP+
show the reaction diagram
-
-
-
-
?
(S)-pulegone + NADPH + H+
(1S,4S)-isomenthone + (1S,4R)-menthone + NADP+
show the reaction diagram
-
-
-
-
?
1-cyclohexene-1-carboxaldehyde + NADPH + H+
cyclohexanecarbaldehyde + NADP+
show the reaction diagram
-
low yields
-
-
?
1-nitrocyclohexene + NADPH + H+
nitrocyclohexane + NADP+
show the reaction diagram
-
-
-
-
?
1-octen-3-one + NADPH + H+
octan-3-one + NADP+
show the reaction diagram
-
-
-
-
?
citral + NADPH + H+
?
show the reaction diagram
-
low yields
-
-
?
trans-2-nonenal + NADPH + H+
nonanal + NADP+
show the reaction diagram
trans-3-nonen-2-one + NADPH + H+
nonan-2-one + NADP+
show the reaction diagram
-
-
-
-
?
trans-cinnamaldehyde + NADPH + H+
3-phenylpropanal + NADP+
show the reaction diagram
-
-
-
-
?
[(1E)-1-nitroprop-1-en-2-yl]benzene + NADPH + H+
[(2R)-1-nitropropan-2-yl]benzene + NADP+
show the reaction diagram
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optically pure form of compound
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-
?
[(1Z)-1-nitroprop-1-en-2-yl]benzene + NADPH + H+
[(2S)-1-nitropropan-2-yl]benzene + NADP+
show the reaction diagram
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poor enantioselectivity
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?
additional information
?
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COFACTOR
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
NAD+
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utilization of NADP+ by the enzyme is four times greater than for NAD+
NADP+
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utilization of NADP+ by the enzyme is four times greater than for NAD+
NADPH
INHIBITORS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
(2E)-3-methylpent-2-enal
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substrate inhibition
1-octen-3-one
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substrate inhibition
2-nonanone
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competitive inhibition versus 3-nonen-2-one and noncompetitive inhibition versus NADPH
NADP+
-
competitive inhibition versus NADPH and noncompetitive inhibition versus 3-nonen-2-one
NADPH
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uncompetitive inhibition
Zn2+
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the addition of 0.25 mM Zn2+ inhibits enzyme activity more than 2fold
KM VALUE [mM]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
590
(1R,2S,4S)-neoisodihydrocarveol
-
pH 8.0, 35C, NADP+
0.837 - 1.032
(2E)-3-methylpent-2-enal
38
(2R,4R)-carveol
-
pH 8.0, 35C, NADP+
52
(2R,4S)-carveol
-
pH 8.0, 35C, NADP+
1.9
(2S,4R)-carveol
-
pH 8.0, 35C, NADP+
2.5
(2S,4S)-carveol
-
pH 8.0, 35C, NADP+
1.4
(R)-pulegone
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recombinant NtRed-1, pH 7.0 and 35C
8.3
(S)-pulegone
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recombinant NtRed-1, pH 7.0 and 35C
0.057 - 0.4
1-nitrocyclohexene
0.004 - 0.032
NADPH
0.0776
trans-2-nonenal
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with trans-3-nonen-2-one as cosubstrate, in 100 mM Tris (pH 7.2), at 25C
0.0282
trans-3-nonen-2-one
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with trans-3-nonen-2-one as cosubstrate, in 100 mM Tris (pH 7.2), at 25C
0.516 - 1
trans-cinnamaldehyde
additional information
additional information
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the Km-values for the (S)-alcohols are one order of magnitude lower than those for the (R)-alcohols, indicating that the enzyme has a higher affinity for the S-configuration than for the R-configuration
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TURNOVER NUMBER [1/s]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.003
(1R,2S,4S)-neoisodihydrocarveol
Nicotiana tabacum
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dehydrogenation, pH 8.0, 35C, NADP+
0.003
(1R,4S)-isodihydrocarvone
Nicotiana tabacum
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hydrogenation to (1R,2S,4S)-neoisodihydrocarveol, pH 7.4, 35C, NADP+
0.66 - 9.2
(2E)-3-methylpent-2-enal
0.02
(2R,4R)-carveol
Nicotiana tabacum
-
dehydrogenation, pH 8.0, 35C, NADP+
0.025
(2R,4S)-carveol
Nicotiana tabacum
-
dehydrogenation, pH 8.0, 35C, NADP+
0.097
(2S,4R)-carveol
Nicotiana tabacum
-
dehydrogenation, pH 8.0, 35C, NADP+
0.077
(2S,4S)-carveol
Nicotiana tabacum
-
dehydrogenation, pH 8.0, 35C, NADP+
0.012 - 0.032
(R)-carvone
3.3
(R)-pulegone
Nicotiana tabacum
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recombinant NtRed-1, pH 7.0 and 35C
0.01 - 0.025
(S)-carvone
2.8
(S)-pulegone
Nicotiana tabacum
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recombinant NtRed-1, pH 7.0 and 35C
1.46 - 11
1-nitrocyclohexene
0.52 - 1.17
1-octen-3-one
1.3
NADPH
Nicotiana tabacum
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app. Kcat, pH 7.3 and 25C, with 1-nitrocyclohexene
0.87 - 2.92
trans-2-nonenal
1.1 - 3.5
trans-cinnamaldehyde
kcat/KM VALUE [1/mMs-1]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
2.4
(R)-pulegone
Nicotiana tabacum
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recombinant NtRed-1, pH 7.0 and 35C
8370
0.34
(S)-pulegone
Nicotiana tabacum
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recombinant NtRed-1, pH 7.0 and 35C
14379
16 - 25.6
1-nitrocyclohexene
19728
2.1 - 2.8
trans-cinnamaldehyde
2225
Ki VALUE [mM]
INHIBITOR
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
2.6
(2E)-3-methylpent-2-enal
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app. Ki value, pH 5.4 and 25C
SPECIFIC ACTIVITY [µmol/min/mg]
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
0.11
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Red-Toyopearl affinity column chromatography, pH 8.0, 35C
4.6
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DEAE-Toyopearl anion exchange column chromatography, pH 8.0, 35C
5300
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crude extract, pH 8.0, 35C
pH OPTIMUM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
5.4
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with 1-nitrocyclohexene
7.4
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reduction of the carbonyl group of (S)-carvone
8
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dehydrogenation of (2S,4S)-carveol
MOLECULAR WEIGHT
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
36300
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native NtRed-1, SDS-PAGE
37000
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alpha2, 2 * 37000, determined by SDS-PAGE
38000
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recombinant NtRed-1, 2 * 38000, gel filtration chromatography
38080
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allyl-ADH1, calculated from sequence
38480
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recombinant NtRed-1, MALDI-TOF MS spectra
SUBUNITS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
homodimer
Crystallization/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
determination of the X-ray crystal structures of holo-, binary (NADP(H)-bound), and ternary (NADP+ and 4-hydroxy-3-methoxycinnamaldehyde-bound) NtDBR complexes
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Purification/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
by DEAE-Toyopearl anion exchange column chromatography, followed by Red-Toyopearl affinity column chromatography
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by DEAEToyopearl and RedToyopearl column chromatography
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Cloned/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
gene cloned into pET21b (Novagen), without a stop codon, to incorporate a C-terminal His6-tag and transformed Escherichia coli strain BL21(DE3)pLysS (Stratagene)
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NtRed-1 cloned in Escherichia coli
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