Information on EC 1.1.1.208 - (+)-neomenthol dehydrogenase

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The enzyme appears in viruses and cellular organisms

EC NUMBER
COMMENTARY hide
1.1.1.208
-
RECOMMENDED NAME
GeneOntology No.
(+)-neomenthol dehydrogenase
REACTION
REACTION DIAGRAM
COMMENTARY hide
ORGANISM
UNIPROT
LITERATURE
(+)-neomenthol + NADP+ = (-)-menthone + NADPH + H+
show the reaction diagram
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-
-
-
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
(+)-neomenthol:NADP+ oxidoreductase
Not identical with EC 1.1.1.207 (-)-menthol dehydrogenase. Acts also on a number of other cyclohexanols and cyclohexenols.
CAS REGISTRY NUMBER
COMMENTARY hide
81811-47-4
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ORGANISM
COMMENTARY hide
LITERATURE
UNIPROT
SEQUENCE DB
SOURCE
pathogen responsive gene AtSDR1
UniProt
Manually annotated by BRENDA team
-
UniProt
Manually annotated by BRENDA team
pathogen responsive gene CaMNR1
UniProt
Manually annotated by BRENDA team
GENERAL INFORMATION
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
metabolism
the enzyme is involved in neomenthol 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
(+)-isomenthol + NADP+
show the reaction diagram
-
low activity
-
-
?
(+)-neomenthol + NADP+
(-)-menthone + NADPH + H+
show the reaction diagram
reaction proceeds via (-)-menthone
-
-
r
(-)-menthone + NADPH
(+)-neomenthol + NADP+
show the reaction diagram
(-)-menthone + NADPH
(3S)-neomenthol + NADP+
show the reaction diagram
(-)-menthone + NADPH + H+
(+)-neomenthol + NADP+
show the reaction diagram
(2R,5R)-isomenthone + NADPH + H+
(+)-neomenthol + NADP+
show the reaction diagram
-
-
-
r
(2S,5R)-menthone + NADPH + H+
(+)-neomenthol + NADP+
show the reaction diagram
-
-
-
r
d-isomenthone + NADPH
d-isomenthol + 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
(+)-isomenthol + NADP+
show the reaction diagram
-
low activity
-
-
?
(-)-menthone + NADPH
(+)-neomenthol + NADP+
show the reaction diagram
(-)-menthone + NADPH
(3S)-neomenthol + NADP+
show the reaction diagram
(-)-menthone + NADPH + H+
(+)-neomenthol + NADP+
show the reaction diagram
Q06ZW2
menthone reduction is the physiological reaction of enzyme MNMR
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-
r
additional information
?
-
COFACTOR
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
NADP+
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
ACTIVATING COMPOUND
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
additional information
CaMNR1 is induced in leaves by bacterial infection and abiotic elicitor treatments. Under drought conditions, the CaMNR1 transcript is rapidly induced within 1 h and thereafter gradually increased to 25 h, while H2O2, cold and mechanical wounding treatment do not induce CaMNR1 expression in pepper leaves
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KM VALUE [mM]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
1
(+)-isomenthone
-
above, pH 9.3, 31C, recombinant enzyme
0.305
(+)-neomenthol
pH 7.0, 30C
0.0071 - 0.674
(-)-menthone
0.0054
NADP+
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pH 9.3, 31C, recombinant enzyme
0.01 - 0.022
NADPH
TURNOVER NUMBER [1/s]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.91
(+)-neomenthol
pH 7.0, 30C
0.06 - 0.6
(-)-menthone
0.2
(2R,5R)-isomenthone
recombinant His6-tagged enzyme, pH 7.0, 30C
-
0.96
(2S,5R)-menthone
recombinant His6-tagged enzyme, pH 7.0, 30C
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0.06
NADPH
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pH 9.3, 31C, recombinant enzyme
kcat/KM VALUE [1/mMs-1]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
2.99
(+)-neomenthol
pH 7.0, 30C
83.6
(-)-menthone
pH 7.0, 30C
pH OPTIMUM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
7.5
reduction reaction
7.6
-
(-)-menthone + NADPH
9
oxidation reaction
additional information
the pH alters the stereospecificity of the enzyme
pH RANGE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
6.5 - 10.5
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50% of maximal activity at pH 6.5 and pH 10.5
TEMPERATURE OPTIMUM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
31
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assay at
pI VALUE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
5.39
sequence calculation
SOURCE TISSUE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
SOURCE
in red, not in green, fruits
Manually annotated by BRENDA team
additional information
CaMNR1 is expressed in an organ-specific manner, no activity in uninduced leaves, stems, roots, or green fruits
Manually annotated by BRENDA team
MOLECULAR WEIGHT
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
34000
gel filtration
34700
1 * 34700, about, sequence calculation
35000
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gel filtration
35722
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x * 35722, amino acid sequence calculation
SUBUNITS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
?
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x * 35722, amino acid sequence calculation
monomer
1 * 34700, about, sequence calculation
Purification/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
recombinant enzyme from Escherichia coli to homogeneity
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
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expression in Escherichia coli
gene AtSDR1, overexpression in Escherichia coli
gene CaMNR1, DNA and amino acid sequence determination and analysis, phylogenetic tree, overexpression in Escherichia coli and in transgenic Arabidopsis thaliana plants
recombinant expression of codon-optimized, C- and N-terminally double-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
ENGINEERING
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
additional information
APPLICATION
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
synthesis
the enzyme is useful, together with menthone:(-)-menthol reductase (EC 1.1.1.207), 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