Information on EC 1.1.1.324 - 8-hydroxygeraniol dehydrogenase

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Substrates: -
Products: -

r

nerol + 2 NADP+

? + 2 NADPH + 2 H+

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Substrates: -
Products: -

r

additional information

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Substrates: various branched-chain allylic primary alcohols, such as nerol, geraniol, and 8-hydroxygeraniol, are substrates, but ethanol is inert. The enzyme is also active with farnesol, 3-methyl-2-buten1-ol, citronellol, 4-isopropylbenzyl alcohol, trans-2-heptenol, and trans-2-hexenol. The enzyme exclusively transfers the pro-R hydrogen of NADPH to neral. No activity with linalool, 2,6-dimethyl-octane, iridodial, 1-octanol, 1-heptanol, 1-pentanol, 3-methyl-3-buten-1-ol, trans-crotyl alcohol, isopulegol, and menthol
Products: -

?

(6E)-8-hydroxygeraniol + 2 NADP+

(6E)-8-oxogeranial + 2 NADPH + 2 H+

(6E)-8-hydroxynerol + 2 NADP+

? + 2 NADPH + 2 H+

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Substrates: -
Products: -

?

additional information

?

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Substrates: various branched-chain allylic primary alcohols, such as nerol, geraniol, and 8-hydroxygeraniol, are substrates, but ethanol is inert. The enzyme is also active with farnesol, 3-methyl-2-buten1-ol, citronellol, 4-isopropylbenzyl alcohol, trans-2-heptenol, and trans-2-hexenol. The enzyme exclusively transfers the pro-R hydrogen of NADPH to neral. No activity with linalool, 2,6-dimethyl-octane, iridodial, 1-octanol, 1-heptanol, 1-pentanol, 3-methyl-3-buten-1-ol, trans-crotyl alcohol, isopulegol, and menthol
Products: -

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NADP+

NADPH

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the enzyme exclusively requires NADP+ or NADPH as the cofactor

additional information

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no activity with NAD+

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Zn2+

additional information

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the enzyme contains no Mo, Co, Cu, Fe, Mn, Mg, Ca, Se, Pt, and Au

1,10-phenanthroline

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79% inhibition at 1.0 mM, 87% at 10 mM

4-chloromercuribenzoate

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complete inhibition at 1 mM and above

EDTA

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44% inhibition at 100 mM

iodoacetamide

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5% inhibition at 1.0 mM, 22% at 10 mM

iridodial

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isopulegol

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menthol

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competitive against 8-hydroxygeraniol

NEM

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55% inhibition at 1.0 mM, complete inhibition at 10 mM

Triton X-100

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potent inhibition at 0.01-0.1%

0.018

NADP+

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with 8-hydroxynerol, pH 9.5, 25°C

additional information

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steady-state kinetic studies show that the nerol dehydrogenation proceeds by an ordered Bi-Bi mechanism, NADP+ binds the enzyme first and then NADPH is the second product released from it, kinetic mechanism, overview

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0.53

menthol

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pH 9.0, 25°C, versus 8-hydroxygeraniol

1417

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purified enzyme, pH 9.5, 25°C

2.7

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purified enzyme, pH 9.0, 25°C

7

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reverse reaction assay at

9

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forward reaction assay at

9.5

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25

5.4

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isoelectric focusing

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UniProt

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low expression level

high expression level

low expression level

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Highest Expressing Human Cell Lines

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metabolism

3 entries

6kj5, download, 3D-view

40000

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1 * 40000 + 1 x 42000, SDS-PAGE

44000

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1 * 44000, SDS-PAGE

50000

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native enzyme, gel filtration

63000

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gel filtration

dimer

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1 * 40000 + 1 x 42000, SDS-PAGE

monomer

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1 * 44000, SDS-PAGE

additional information

the enzyme rapidly and irreversibly loses its activity when 1 mM dithiothreitol and 20% glycerol v/v are omitted from the enzyme solution

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-20°C, purified enzyme, 20 mM Tris HCl, pH 8.0, 20% glycerol, 1 mM DTT, 6 months without loss of activity

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native enzyme 1149fold from leaves to homogeneity by ultracentrifugation, ammonium sulfate fractionation, hydrophobic inetraction and anion exchange chromatography, affinity chromatography, and gel filtration

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native enzyme to homogeneity by ammonium sulfate fractionation, hydrophobic interaction, anion exchange, and AF-Red dye affinity chromatography followed by gel filtration

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gene 8HGO, reporter plasmids for transient protoplast assays of enzyme expression are generated by cloning the GES, G10H, 8HGO, IS, IO, 7-DLGT, and 7DLH promoters upstream of a firefly luciferase (LUC) reporter and rbcS terminator

Catharanthus roseus

W8JWV8

763575

the enzyme expression is activated by transcription factor BIS3, i.e. BHLH iridoid synthesis 3, a basic helix-loop-helix (bHLH) transcription factor and key regulators of plant specialized metabolites, including terpenoid indole alkaloids, in Catharanthus roseus plants. BIS3 is clustered with BIS2 and BIS1 in a bHLH gene cluster. Similar to the iridoid pathway genes, BIS3 is highly expressed in roots and induced by methyl jasmonate. Transactivation of the promoters is abolished when BIS3 is converted to a dominant repressor by fusing with the ERF-associated amphiphilic repression (EAR) sequence (BIS3-SRDX)

Catharanthus roseus

W8JWV8

763575

additional information

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plant (4aR,7S,7aS)-nepetalactone can be used for synthesis of (4aR,7S,7aS)-nepetalactol, an aphid pheromone, useful in aphid control