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Enzyme Nomenclature
Information on EC 1.1.1.208 - (+)-neomenthol dehydrogenase
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The enzyme appears in viruses and cellular organisms
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EC NUMBER 
COMMENTARY 
1.1.1.208
-
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RECOMMENDED NAME
GeneOntology No.
(+)-neomenthol dehydrogenase
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REACTION
REACTION DIAGRAM
COMMENTARY
ORGANISM
UNIPROT
LITERATURE
(+)-neomenthol + NADP+ = (-)-menthone + NADPH + H+
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REACTION TYPE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
oxidation
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-
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redox reaction
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reduction
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-
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PATHWAY
BRENDA Link
KEGG Link
MetaCyc Link
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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.
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CAS REGISTRY NUMBER
COMMENTARY
81811-47-4
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ORGANISM
COMMENTARY
LITERATURE
UNIPROT
SEQUENCE DB
SOURCE
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GENERAL INFORMATION
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
metabolism
the enzyme is involved in neomenthol biosynthesis in the peppermint pathway, overview
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SUBSTRATE
PRODUCT
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate)
(Substrate)
LITERATURE
(Substrate)
(Substrate)
COMMENTARY
(Product)
(Product)
LITERATURE
(Product)
(Product)
Reversibility
r=reversible
ir=irreversible
?=not specified
r=reversible
ir=irreversible
?=not specified
(+)-neomenthol + NADP+
(-)-menthone + NADPH + H+
reaction proceeds via (-)-menthone
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-
r
(-)-menthone + NADPH
(3S)-neomenthol + NADP+
in vitro antimicrobial activities of menthone, neomenthol and menthol, overview
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r
(-)-menthone + NADPH
(3S)-neomenthol + NADP+
CaMNR1 converts (-)-menthone to 93% (3S)-neomenthol and 7% (3R)-menthol at pH 7.5, and to 72% (3S)-neomenthol and 28% (3R)-menthol at pH 9.0 with NADPH as a cofactor
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r
(-)-menthone + NADPH
(3S)-neomenthol + NADP+
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low activity in the reverse reaction
(3S)-neomenthol is the main product, product determination by gas chromatography, overview
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r
(-)-menthone + NADPH + H+
(+)-neomenthol + NADP+
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main product, plus some (-)-menthol
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r
(-)-menthone + NADPH + H+
(+)-neomenthol + NADP+
menthone reduction is the physiological reaction of enzyme MNMR
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r
additional information
?
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the menthone reductase gene CaMNR1 positively regulates plant defenses against a broad spectrum of pathogens, overview
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additional information
?
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no substrates for reduction: carvone and isopiperitenone. No substrates in dehydrogenase reaction: (+)-borneol, (-)-borneol, (+)-menthol and (-)-neomenthol
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additional information
?
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CaMNR1 gene plays a role in regulating the resistance of pepper plants at the mRNA and protein levels, the menthone reductase gene CaMNR1 positively regulates plant defenses against a broad spectrum of pathogens, overview
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additional information
?
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primary monoterpene biosynthesis pathway, overview
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additional information
?
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enzyme MNMR has a preference for menthone over isomenthone
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NATURAL SUBSTRATES
NATURAL PRODUCTS
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate)
(Substrate)
LITERATURE
(Substrate)
(Substrate)
COMMENTARY
(Product)
(Product)
LITERATURE
(Product)
(Product)
REVERSIBILITY
r=reversible
ir=irreversible
?=not specified
r=reversible
ir=irreversible
?=not specified
(-)-menthone + NADPH + H+
(+)-neomenthol + NADP+
Q06ZW2
menthone reduction is the physiological reaction of enzyme MNMR
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r
(-)-menthone + NADPH
(3S)-neomenthol + NADP+
B2X050
in vitro antimicrobial activities of menthone, neomenthol and menthol, overview
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r
additional information
?
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Q9M2E2
the menthone reductase gene CaMNR1 positively regulates plant defenses against a broad spectrum of pathogens, overview
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-
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additional information
?
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B2X050
CaMNR1 gene plays a role in regulating the resistance of pepper plants at the mRNA and protein levels, the menthone reductase gene CaMNR1 positively regulates plant defenses against a broad spectrum of pathogens, overview
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additional information
?
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primary monoterpene biosynthesis pathway, overview
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COFACTOR
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
NADPH
the enzyme contains the coenzyme binding domain motif I: GxxxGxG
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INHIBITORS
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
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ACTIVATING COMPOUND
ORGANISM
UNIPROT
COMMENTARY
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
LITERATURE
IMAGE
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TURNOVER NUMBER [1/s]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
0.2
(2R,5R)-isomenthone
recombinant His6-tagged enzyme, pH 7.0, 30°C
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0.96
(2S,5R)-menthone
recombinant His6-tagged enzyme, pH 7.0, 30°C
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kcat/KM VALUE [1/mMs-1]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
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pH OPTIMUM
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
additional information
the pH alters the stereospecificity of the enzyme
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pH RANGE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
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TEMPERATURE OPTIMUM
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
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pI VALUE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
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SOURCE TISSUE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
SOURCE
additional information
CaMNR1 is expressed in an organ-specific manner, no activity in uninduced leaves, stems, roots, or green fruits
the enzyme is induced in pepper leaves during compatible and incompatible interactions with Xcv, and by bacterial infection and abiotic elicitor treatments
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PDB
SCOP
CATH
ORGANISM
UNIPROT
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MOLECULAR WEIGHT
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
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SUBUNITS
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
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Purification/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
recombinant enzyme from Escherichia coli to homogeneity
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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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
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ENGINEERING
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
additional information
additional information
AtSDR1 virus-induced gene silencing and ectopic overexpression in Arabidopsis thaliana plants leads to significantly more susceptible to Xanthomonas campestris pv. vesicatoria and Colletotrichum coccodes infection, and lower expression levels of salicylic acidresponsive CaBPR1 and CaPR10 and jasmonic acid-responsive CaDEF1 compared to wild-type plants, phenotype, overview
additional information
CaMNR1 tobacco rattle virus-mediated virus-induced gene silencing and ectopic overexpression in pepper and Arabidopsis thaliana plants, transgenic CaMNR1-silenced pepper plants are significantly more susceptible to Xanthomonas campestris pv. vesicatoria and Colletotrichum coccodes infection, and express lower levels of salicylic acidresponsive CaBPR1 and CaPR10 and jasmonic acid-responsive CaDEF1 compared to wild-type plants, while CaMNR1-overexpression transgenic Arabidopsis thaliana plants exhibit enhanced resistance to the hemi-biotrophic pathogen Pseudomonas syringae pv. tomato DC3000 and the biotrophic pathogen Hyaloperonospora parasitica isolate Noco2, accompanied by induction of AtPR1 and AtPDF1.2, phenotypes, overview
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
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
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LINKS TO OTHER DATABASES (specific for EC-Number 1.1.1.208)
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