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Literature summary for 1.1.1.324 extracted from

  • Ikeda, H.; Esaki, N.; Nakai, S.; Hashimoto, K.; Uesato, S.; Soda, K.; Fujita, T.
    Acyclic monoterpene primary alcohol:NADP+ oxidoreductase of Rauwolfia serpentina cells: the key enzyme in biosynthesis of monoterpene alcohols (1991), J. Biochem., 109, 341-347.
    View publication on PubMed

General Stability

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

Inhibitors

Inhibitors Comment Organism Structure
iridodial
-
Rauvolfia serpentina
isopulegol
-
Rauvolfia serpentina
menthol competitive against 8-hydroxygeraniol Rauvolfia serpentina

KM Value [mM]

KM Value [mM] KM Value Maximum [mM] Substrate Comment Organism Structure
additional information
-
additional information 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 Rauvolfia serpentina

Metals/Ions

Metals/Ions Comment Organism Structure
additional information the enzyme contains no Mo, Co, Cu, Fe, Mn, Mg, Ca, Se, Pt, and Au Rauvolfia serpentina
Zn2+ the enzyme contains zinc ions Rauvolfia serpentina

Molecular Weight [Da]

Molecular Weight [Da] Molecular Weight Maximum [Da] Comment Organism
44000
-
1 * 44000, SDS-PAGE Rauvolfia serpentina
50000
-
native enzyme, gel filtration Rauvolfia serpentina

Natural Substrates/ Products (Substrates)

Natural Substrates Organism Comment (Nat. Sub.) Natural Products Comment (Nat. Pro.) Rev. Reac.
(6E)-8-hydroxygeraniol + 2 NADP+ Rauvolfia serpentina 10-hydroxygeraniol undergoes a reversible dehydrogenation to produce 8-oxogeraniol or 8-hydroxygeranial, which are oxidized further to give 8-oxogeranial, the direct precursor of iridodial (6E)-8-oxogeranial + 2 NADPH + 2 H+
-
r
additional information Rauvolfia serpentina 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 ?
-
?

Organism

Organism UniProt Comment Textmining
Rauvolfia serpentina
-
-
-

Purification (Commentary)

Purification (Comment) Organism
native enzyme to homogeneity by ammonium sulfate fractionation, hydrophobic interaction, anion exchange, and AF-Red dye affinity chromatography followed by gel filtration Rauvolfia serpentina

Specific Activity [micromol/min/mg]

Specific Activity Minimum [µmol/min/mg] Specific Activity Maximum [µmol/min/mg] Comment Organism
2.7
-
purified enzyme, pH 9.0, 25°C Rauvolfia serpentina

Storage Stability

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

Substrates and Products (Substrate)

Substrates Comment Substrates Organism Products Comment (Products) Rev. Reac.
(6E)-8-hydroxygeraniol + 2 NADP+
-
Rauvolfia serpentina (6E)-8-oxogeranial + 2 NADPH + 2 H+
-
r
(6E)-8-hydroxygeraniol + 2 NADP+ 10-hydroxygeraniol undergoes a reversible dehydrogenation to produce 8-oxogeraniol or 8-hydroxygeranial, which are oxidized further to give 8-oxogeranial, the direct precursor of iridodial Rauvolfia serpentina (6E)-8-oxogeranial + 2 NADPH + 2 H+
-
r
(6E)-8-hydroxynerol + 2 NADP+
-
Rauvolfia serpentina ? + 2 NADPH + 2 H+
-
r
geraniol + 2 NADP+
-
Rauvolfia serpentina ? + 2 NADPH + 2 H+
-
r
additional information 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 Rauvolfia serpentina ?
-
?
nerol + 2 NADP+
-
Rauvolfia serpentina ? + 2 NADPH + 2 H+
-
r

Subunits

Subunits Comment Organism
monomer 1 * 44000, SDS-PAGE Rauvolfia serpentina

Synonyms

Synonyms Comment Organism
acyclic monoterpene primary alcohol:NADP+ oxidoreductase
-
Rauvolfia serpentina

Temperature Optimum [°C]

Temperature Optimum [°C] Temperature Optimum Maximum [°C] Comment Organism
25
-
assay at Rauvolfia serpentina

pH Optimum

pH Optimum Minimum pH Optimum Maximum Comment Organism
7
-
reverse reaction assay at Rauvolfia serpentina
9
-
forward reaction assay at Rauvolfia serpentina

Cofactor

Cofactor Comment Organism Structure
NADP+ the enzyme exclusively requires NADP+ or NADPH as the cofactor Rauvolfia serpentina
NADPH the enzyme exclusively requires NADP+ or NADPH as the cofactor Rauvolfia serpentina

Ki Value [mM]

Ki Value [mM] Ki Value maximum [mM] Inhibitor Comment Organism Structure
0.53
-
menthol pH 9.0, 25°C, versus 8-hydroxygeraniol Rauvolfia serpentina

pI Value

Organism Comment pI Value Maximum pI Value
Rauvolfia serpentina isoelectric focusing
-
5.4

General Information

General Information Comment Organism
metabolism the acyclic monoterpene primary alcohol:NADP+ oxidoreductase of Rauwolfia serpentina is a key enzyme in biosynthesis of monoterpene alcohols in the plant Rauvolfia serpentina