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discounted EARLY registration ends Dec 31, 2014
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MetaCyc Enzyme: acyclic monoterpene primary alcohol oxidoreductase

Synonyms: acyclic monoterpene primary alcohol dehydrogenase

Species: Rauvolfia serpentina

Summary:
Catalyzes the sequential oxidation of 10-hydroxygeraniol to its C-1 or C-10 aldehydes, then to 10-oxogeranial. 10-oxogeranial is a precursor for the biosynthesis of iridoid monoterpenes, monoterpenes with a methylcyclopentane skeleton. Iridoids are also precursors of indole alkaloids such as strictosidine (see secologanin and strictosidine biosynthesis).

The enzyme contains zinc ion. NADP but not NAD is the required cofactor.

The enzyme purified from Rauwolfia serpentine was a monomer. It specifically acted on primary alcohols. Secondary alcohols were not accepted. In addition to 10-hydroxygeraniol, the enzyme was also active towards geraniol and nerol. It had a 10 times lower affinity for 10-hydroxygeraniol than for geraniol. The highest enzyme activity was with nerol.

Molecular Weight of Polypeptide: 44.0 kD (experimental) [Ikeda91b ]

pI: 5.4 [Ikeda91b]

Gene-Reaction Schematic: ?

Credits:
Created 25-Apr-2008 by Zhang P , TAIR


Enzymatic reaction of: 8-hydroxygeraniol dehydrogenase (acyclic monoterpene primary alcohol oxidoreductase)

EC Number: 1.1.1.324

(6E)-8-hydroxygeraniol + 2 NADP+ <=> (6E)-8-oxogeranial + 2 NADPH + 2 H+

The reaction direction shown, that is, A + B ↔ C + D versus C + D ↔ A + B, is in accordance with the Enzyme Commission system.

The reaction is favored in the direction shown.

In Pathways: secologanin and strictosidine biosynthesis

Cofactors or Prosthetic Groups: Zn2+ [Ikeda91b]


Enzymatic reaction of: 10-hydroxygeranial oxidoreductase (acyclic monoterpene primary alcohol oxidoreductase)

EC Number: 1.1.1.-

(6E)-8-hydroxygeranial + NADP+ <=> (6E)-8-oxogeranial + NADPH + H+

The reaction direction shown, that is, A + B ↔ C + D versus C + D ↔ A + B, is in accordance with the direction of enzyme catalysis.

The reaction is irreversible in the direction shown. [Ikeda91b]

Cofactors or Prosthetic Groups: Zn2+ [Ikeda91b]


Enzymatic reaction of: 10-oxogeraniol oxidoreductase (acyclic monoterpene primary alcohol oxidoreductase)

EC Number: 1.1.1.-

(6E)-8-oxogeraniol + NADP+ <=> (6E)-8-oxogeranial + NADPH + H+

The reaction direction shown, that is, A + B ↔ C + D versus C + D ↔ A + B, is in accordance with the direction of enzyme catalysis.

This reaction is reversible. [Ikeda91b]

Cofactors or Prosthetic Groups: Zn2+ [Ikeda91b]


Enzymatic reaction of: 10-oxogeraniol dehydrogenase (acyclic monoterpene primary alcohol oxidoreductase)

EC Number: 1.1.1.-

(6E)-8-hydroxygeraniol + NADP+ <=> (6E)-8-oxogeraniol + NADPH + H+

The reaction direction shown, that is, A + B ↔ C + D versus C + D ↔ A + B, is in accordance with the direction of enzyme catalysis.

This reaction is reversible. [Ikeda91b]

Cofactors or Prosthetic Groups: Zn2+ [Ikeda91b]

Inhibitors (Competitive): (-)-menthol [Ikeda91b]

pH(opt): 9 [Ikeda91b]


Enzymatic reaction of: 10-hydroxygeraniol oxidoreductase (acyclic monoterpene primary alcohol oxidoreductase)

EC Number: 1.1.1.-

(6E)-8-hydroxygeraniol + NADP+ <=> (6E)-8-hydroxygeranial + NADPH + H+

The reaction direction shown, that is, A + B ↔ C + D versus C + D ↔ A + B, is in accordance with the direction of enzyme catalysis.

This reaction is reversible. [Ikeda91b]

Alternative Substrates for (6E)-8-hydroxygeranial: geraniol [Ikeda91b ] , nerol [Ikeda91b ]

Cofactors or Prosthetic Groups: Zn2+ [Ikeda91b]

Inhibitors (Competitive): (-)-menthol [Ikeda91b]

Kinetic Parameters:

Substrate
Km (μM)
Citations
(6E)-8-hydroxygeranial
700.0
[Ikeda91b]

pH(opt): 9 [Ikeda91b]


References

Ikeda91b: Ikeda H, Esaki N, Nakai S, Hashimoto K, Uesato S, Soda K, Fujita T (1991). "Acyclic monoterpene primary alcohol:NADP+ oxidoreductase of Rauwolfia serpentina cells: the key enzyme in biosynthesis of monoterpene alcohols." J Biochem 109(2);341-7. PMID: 1864846


Report Errors or Provide Feedback
Please cite the following article in publications resulting from the use of MetaCyc: Caspi et al, Nucleic Acids Research 42:D459-D471 2014
Page generated by SRI International Pathway Tools version 18.5 on Mon Dec 22, 2014, BIOCYC13A.