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

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EC NUMBER
COMMENTARY hide
1.1.1.207
-
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RECOMMENDED NAME
GeneOntology No.
(-)-menthol dehydrogenase
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REACTION
REACTION DIAGRAM
COMMENTARY hide
ORGANISM
UNIPROT
LITERATURE
(-)-menthol + NADP+ = (-)-menthone + NADPH + H+
show the reaction diagram
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-
-
-
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REACTION TYPE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
oxidation
-
-
-
-
redox reaction
-
-
-
-
reduction
-
-
-
-
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PATHWAY
BRENDA Link
KEGG Link
MetaCyc Link
menthol biosynthesis
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Monoterpenoid biosynthesis
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Biosynthesis of secondary metabolites
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-
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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.
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CAS REGISTRY NUMBER
COMMENTARY hide
81811-46-3
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ORGANISM
COMMENTARY hide
LITERATURE
UNIPROT
SEQUENCE DB
SOURCE
-
-
-
Manually annotated by BRENDA team
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GENERAL INFORMATION
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
metabolism
the enzyme is involved in menthol biosynthesis in the peppermint pathway, overview
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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
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-
-
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
?
-
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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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-
-
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COFACTOR
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
NADPH
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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
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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
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TURNOVER NUMBER [1/s]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.6
(-)-menthone
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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
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pH OPTIMUM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
7.5
-
(-)-menthone + NADPH
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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
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TEMPERATURE OPTIMUM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
31
-
assay at
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SOURCE TISSUE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
SOURCE
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MOLECULAR WEIGHT
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
34070
-
x * 34070, amino acid sequence calculation
35000
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gel filtration
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SUBUNITS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
?
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x * 34070, amino acid sequence calculation
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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
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Cloned/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
DNA and amino acid sequence determination and analysis, expression in Escherichia coli
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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
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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
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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
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LINKS TO OTHER DATABASES (specific for EC-Number 1.1.1.207)
ExplorEnz
ExPASy
KEGG
MetaCyc
SABIO-RK
NCBI: PubMed, Protein, Nucleotide, Structure, Genome, OMIM
IUBMB Enzyme Nomenclature
PROSITE Database of protein families and domains
InterPro (database of protein families, domains and functional sites)