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EC Tree
IUBMB Comments The enzyme, characterized from the plant Antirrhinum majus (snapdragon), is involved in biosynthesis of 7-epi-iridoids such as antirrhinoside. The enzyme catalyses the stereospecific reduction of 8-oxogeranial, forming an unstable product that in the absence of additional cylases undergoes spontaneous cyclization to (-)-cis,trans-nepetalactol. cf. EC 1.3.1.122, (S)-8-oxocitronellyl enol synthase.
The enzyme appears in viruses and cellular organisms
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multisubstrate oxido-reductase
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iridoid synthase
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(R)-8-oxocitronellyl enol + NADP+ = (6E)-8-oxogeranial + NADPH + H+
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(R)-8-oxocitronellyl enol:NADP+ oxidoreductase
The enzyme, characterized from the plant Antirrhinum majus (snapdragon), is involved in biosynthesis of 7-epi-iridoids such as antirrhinoside. The enzyme catalyses the stereospecific reduction of 8-oxogeranial, forming an unstable product that in the absence of additional cylases undergoes spontaneous cyclization to (-)-cis,trans-nepetalactol. cf. EC 1.3.1.122, (S)-8-oxocitronellyl enol synthase.
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(6E)-8-oxogeranial + NADPH + H+
(R)-8-oxocitronellal + (S)-8-oxocitronellal + NADP+
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?
(6E)-8-oxogeranial + NADPH + H+
(R)-8-oxocitronellyl enol + NADP+
(6E)-8-oxogeranial + NADPH + H+
nepetalactol + iridodial + NADP+
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isoform IS2 has a lower affinity than IS1 for (6E)-8-oxogeranial
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?
(6E)-8-oxogeranial + NADPH + H+
(R)-8-oxocitronellyl enol + NADP+
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?
(6E)-8-oxogeranial + NADPH + H+
(R)-8-oxocitronellyl enol + NADP+
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?
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(6E)-8-oxogeranial + NADPH + H+
(R)-8-oxocitronellal + (S)-8-oxocitronellal + NADP+
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?
(6E)-8-oxogeranial + NADPH + H+
(R)-8-oxocitronellyl enol + NADP+
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?
(6E)-8-oxogeranial + NADPH + H+
nepetalactol + iridodial + NADP+
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isoform IS2 has a lower affinity than IS1 for (6E)-8-oxogeranial
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?
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NADPH
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0.0011 - 0.368
(6E)-8-oxogeranial
0.0011
(6E)-8-oxogeranial
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with NADPH as cosubstrate, at pH 7.0 and 25°C
0.00729
(6E)-8-oxogeranial
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isoform IS1, at pH 7.0 and 25°C
0.05437
(6E)-8-oxogeranial
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isoform IS2, at pH 7.0 and 25°C
0.368
(6E)-8-oxogeranial
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at pH 7.0, temperature not specified in the publication
0.04183
NADPH
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isoform IS2, at pH 7.0 and 25°C
0.07794
NADPH
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isoform IS1, at pH 7.0 and 25°C
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0.034 - 2.6
(6E)-8-oxogeranial
0.034
(6E)-8-oxogeranial
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isoform IS2, at pH 7.0 and 25°C
0.11
(6E)-8-oxogeranial
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isoform IS1, at pH 7.0 and 25°C
0.72
(6E)-8-oxogeranial
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with NADPH as cosubstrate, at pH 7.0 and 25°C
2.6
(6E)-8-oxogeranial
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at pH 7.0, temperature not specified in the publication
0.026
NADPH
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isoform IS2, at pH 7.0 and 25°C
0.135
NADPH
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isoform IS1, at pH 7.0 and 25°C
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0.628 - 15.56
(6E)-8-oxogeranial
0.628
(6E)-8-oxogeranial
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isoform IS2, at pH 7.0 and 25°C
15.56
(6E)-8-oxogeranial
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isoform IS1, at pH 7.0 and 25°C
0.628
NADPH
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isoform IS2, at pH 7.0 and 25°C
1.73
NADPH
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isoform IS1, at pH 7.0 and 25°C
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snapdragon
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brenda
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brenda
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brenda
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lowest expression
brenda
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brenda
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brenda
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highest expression
brenda
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brenda
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metabolism
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the enzyme plays a role in antirrhinoside biosynthesis
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?
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x * 40000, SDS-PAGE
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x * 46000, isoform IS2, SDS-PAGE
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x * 88000, isoform IS1, SDS-PAGE
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in complex with NADP+ and 8-oxogeranial, hanging drop vapor diffusion method, using 0.1 M Bis-Tris Propane, 5% (v/v) glycerol, and 16.5-19% (w/v) PEG 5000 MME
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V150M
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the mutant shows increased specific activity with respect to progesterone, accepting both citral and progesterone as substrate, with a clear preference for citral
V150M/I156Y
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the double mutant shows increased specific activity with respect to progesterone, accepting both citral and progesterone as substrate, with a clear preference for citral
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His Trap column chromatography
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His-Trap column chromatography and Superdex S200 gel filtration
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Ni-NTA column chromatography and Superdex S200 gel filtration
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expressed in Escherichia coli BL21 (DE3) cells
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expressed in Escherichia coli BL21(DE3) cells
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expressed in Escherichia coli soluBL21 (DE3) cells
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Lichman, B.; O'Connor, S.; Kries, H.
Biocatalytic strategies towards [4+2] cycloadditions
Chemistry
25
6864-6877
2019
Antirrhinum majus
brenda
Kries, H.; Kellner, F.; Kamileen, M.; O'Connor, S.
Inverted stereocontrol of iridoid synthase in snapdragon
J. Biol. Chem.
292
14659-14667
2017
Antirrhinum majus
brenda
Xiang, B.; Li, X.; Wang, Y.; Tian, X.; Yang, Z.; Ma, L.; Liu, X.; Wang, Y.
Cloning and characterization of two iridoid synthase homologs from Swertia mussotii
Molecules
22
E1387
2017
Swertia mussotii
brenda
Fellows, R.; Russo, C.M.; Silva, C.S.; Lee, S.G.; Jez, J.M.; Chisholm, J.D.; Zubieta, C.; Nanao, M.H.
A multisubstrate reductase from Plantago major structure-function in the short chain reductase superfamily
Sci. Rep.
8
14796
2018
Plantago major
brenda
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1.3.1.123 8-oxogeranial reductase
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