Information on EC 1.1.1.207 - (-)-menthol dehydrogenase

for references in articles please use BRENDA:EC1.1.1.207
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The expected taxonomic range for this enzyme is: Mentha

EC NUMBER
COMMENTARY hide
1.1.1.207
-
RECOMMENDED NAME
GeneOntology No.
(-)-menthol dehydrogenase
REACTION
REACTION DIAGRAM
COMMENTARY hide
ORGANISM
UNIPROT
LITERATURE
(-)-menthol + NADP+ = (-)-menthone + NADPH + H+
show the reaction diagram
-
-
-
-
REACTION TYPE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
oxidation
-
-
-
-
redox reaction
-
-
-
-
reduction
-
-
-
-
PATHWAY
BRENDA Link
KEGG Link
MetaCyc Link
menthol biosynthesis
-
-
Monoterpenoid biosynthesis
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Biosynthesis of secondary metabolites
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-
SYSTEMATIC NAME
IUBMB Comments
(-)-menthol:NADP+ oxidoreductase
Not identical with EC 1.1.1.208 (+)-neomenthol dehydrogenase. Acts also on a number of other cyclohexanols and cyclohexenols.
CAS REGISTRY NUMBER
COMMENTARY hide
81811-46-3
-
ORGANISM
COMMENTARY hide
LITERATURE
UNIPROT
SEQUENCE DB
SOURCE
-
-
-
Manually annotated by BRENDA team
GENERAL INFORMATION
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
metabolism
the enzyme is involved in menthol biosynthesis in the peppermint pathway, overview
SUBSTRATE
PRODUCT                       
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate) hide
LITERATURE
(Substrate)
COMMENTARY
(Product) hide
LITERATURE
(Product)
Reversibility
r=reversible
ir=irreversible
?=not specified
(+)-isomenthone + NADPH
(+)-neoisomenthol + NADP+
show the reaction diagram
-
-
-
-
?
(-)-menthone + NADPH
(3R)-menthol + NADP+
show the reaction diagram
(-)-menthone + NADPH + H+
(-)-menthol + NADP+
show the reaction diagram
(1R)-menthone + NADPH
(1R)-menthol + NADP+
show the reaction diagram
(1R)-menthone + NADPH
(1R)-menthole + NADP+
show the reaction diagram
(2R,5R)-isomenthone + NADPH + H+
(-)-menthol + NADP+
show the reaction diagram
-
-
-
r
(2S,5R)-menthone + NADPH + H+
(-)-menthol + NADP+
show the reaction diagram
-
-
-
r
d-isomenthone + NADPH
d-neoisomenthol + NADP+
show the reaction diagram
additional information
?
-
NATURAL SUBSTRATES
NATURAL PRODUCTS
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate) hide
LITERATURE
(Substrate)
COMMENTARY
(Product) hide
LITERATURE
(Product)
REVERSIBILITY
r=reversible
ir=irreversible
?=not specified
(+)-isomenthone + NADPH
(+)-neoisomenthol + NADP+
show the reaction diagram
-
-
-
-
?
(-)-menthone + NADPH
(3R)-menthol + NADP+
show the reaction diagram
-
-
-
-
?
(-)-menthone + NADPH + H+
(-)-menthol + NADP+
show the reaction diagram
Q5CAF4
menthone reduction is the physiological reaction of enzyme MMR
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-
r
(1R)-menthone + NADPH
(1R)-menthole + NADP+
show the reaction diagram
additional information
?
-
-
primary monoterpene biosynthesis pathway, overview
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-
-
COFACTOR
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
NADPH
INHIBITORS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
Hg2+
-
almost complete inhibition at 0.25 mM
iodoacetamide
-
almost complete inhibition at 0.25 mM
N-ethylmaleimide
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almost complete inhibition at 0.25 mM
p-hydroxymercuribenzoate
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almost complete inhibition at 0.05 mM
KM VALUE [mM]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.041
(+)-isomenthone
-
pH 7.0, 31°C, recombinant enzyme
0.003 - 0.25
(-)-menthone
0.00012 - 0.015
NADPH
TURNOVER NUMBER [1/s]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.6
(-)-menthone
-
pH 7.0, 31°C, recombinant enzyme
2
(2R,5R)-isomenthone
recombinant His6-tagged enzyme, pH 7.0, 30°C
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1.63
(2S,5R)-menthone
recombinant His6-tagged enzyme, pH 7.0, 30°C
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0.6
NADPH
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pH 7.0, 31°C, recombinant enzyme
pH OPTIMUM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
7.5
-
(-)-menthone + NADPH
pH RANGE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
4.5 - 8.5
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50% of maximal activity at pH 4.5 and pH 8.5
TEMPERATURE OPTIMUM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
31
-
assay at
SOURCE TISSUE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
SOURCE
MOLECULAR WEIGHT
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
34070
-
x * 34070, amino acid sequence calculation
35000
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gel filtration
SUBUNITS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
?
-
x * 34070, amino acid sequence calculation
Purification/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
recombinant enzyme partially
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recombinant His6-tagged enzyme from Escherichia coli strain NiCO2(DE3) by nickel affinity chromatography and gel filtration
Cloned/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
DNA and amino acid sequence determination and analysis, expression in Escherichia coli
-
recombinant expression of codon-optimized, C-terminally His6-tagged enzyme in Escherichia coli strain BL21(DE3)pLysS, recombinant expression of three multigene constructs: (i) NtDBR-His6-SD-MMRHis6-SD-His6-MNMR (DMN), (ii) NtDBR-His6-SD-MMRHis6 (DM), and (iii) NtDBR-His6-SD-His6-MNMR in Escherichia coli strain NiCO2(DE3), optimization of multigene expression
EXPRESSION
ORGANISM
UNIPROT
LITERATURE
transcript level of menthol dehydrogenase/menthone reductase is highly upregulated in plants treated with calliterpenone, leading to increased content of menthone and menthol in oil
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ENGINEERING
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
additional information
development of a one-pot (bio)synthesis of (1R,2S,5R)-(-)-menthol and (1S,2S,5R)-(+)-neomenthol from pulegone, using recombinant Escherichia coli extracts that contain the biosynthetic genes for an ene-reductase NtDBR from Nicotiana tabacum and two menthone dehydrogenases, MMR and MNMR from Mentha piperita, a modular engineering strategy to improve the final production level. Multigene-construct-derived enzyme mixtures production of menthone, isomenthone, menthol, and neomenthol, but no or poor production of neoisomenthol and isomenthol, overview
APPLICATION
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
agriculture
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transcript level of menthol dehydrogenase/menthone reductase is highly upregulated in plants treated with calliterpenone, leading to increased content of menthone and menthol in oil
synthesis
the enzyme is useful, together with menthone:(+)-neomenthol reductase (EC 1.1.1.208), for production of (1R,2S,5R)-(-)-menthol and (1S,2S,5R)-(+)-neomenthol from pulegone, development of a one-pot synthesis method, overview. Menthol isomers, (1R,2S,5R)-(-)-menthol, (1R,2S,5S)-(+)-isomenthol, (1S,2S,5R)-(+)-neomenthol, and (1R,2R,5R)-(+)-neoisomenthol, and carvone are used as additives in oral hygiene products and flavors in food and beverages, or cosmetics