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show all sequences of 1.1.1.208

Enzymatic menthol production: one-pot approach using engineered Escherichia coli

Toogood, H.; Cheallaigh, A.; Tait, S.; Mansell, D.; Jervis, A.; Lygidakis, A.; Humphreys, L.; Takano, E.; Gardiner, J.; Scrutton, N.; ACS Synth. Biol. 4, 1112-1123 (2015)

Data extracted from this reference:

Application
Application
Commentary
Organism
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
Mentha x piperita
Cloned(Commentary)
Commentary
Organism
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
Mentha x piperita
Engineering
Amino acid exchange
Commentary
Organism
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
Mentha x piperita
Natural Substrates/ Products (Substrates)
Natural Substrates
Organism
Commentary (Nat. Sub.)
Natural Products
Commentary (Nat. Pro.)
Organism (Nat. Pro.)
Reversibility
(-)-menthone + NADPH + H+
Mentha x piperita
menthone reduction is the physiological reaction of enzyme MNMR
(+)-neomenthol + NADP+
-
-
r
Organism
Organism
Primary Accession No. (UniProt)
Commentary
Textmining
Mentha x piperita
Q06ZW2
-
-
Purification (Commentary)
Commentary
Organism
recombinant His6-tagged enzyme from Escherichia coli strain NiCO2(DE3) by nickel affinity chromatography and gel filtration
Mentha x piperita
Substrates and Products (Substrate)
Substrates
Commentary Substrates
Literature (Substrates)
Organism
Products
Commentary (Products)
Literature (Products)
Organism (Products)
Reversibility
(-)-menthone + NADPH + H+
-
739778
Mentha x piperita
(+)-neomenthol + NADP+
-
-
-
r
(-)-menthone + NADPH + H+
menthone reduction is the physiological reaction of enzyme MNMR
739778
Mentha x piperita
(+)-neomenthol + NADP+
-
-
-
r
(2R,5R)-isomenthone + NADPH + H+
-
739778
Mentha x piperita
(+)-neomenthol + NADP+
-
-
-
r
(2S,5R)-menthone + NADPH + H+
-
739778
Mentha x piperita
(+)-neomenthol + NADP+
-
-
-
r
additional information
enzyme MNMR has a preference for menthone over isomenthone
739778
Mentha x piperita
?
-
-
-
-
Temperature Optimum [C]
Temperature Optimum [C]
Temperature Optimum Maximum [C]
Commentary
Organism
30
-
assay at
Mentha x piperita
Turnover Number [1/s]
Turnover Number Minimum [1/s]
Turnover Number Maximum [1/s]
Substrate
Commentary
Organism
Structure
0.2
-
(2R,5R)-isomenthone
recombinant His6-tagged enzyme, pH 7.0, 30C
Mentha x piperita
0.96
-
(2S,5R)-menthone
recombinant His6-tagged enzyme, pH 7.0, 30C
Mentha x piperita
Cofactor
Cofactor
Commentary
Organism
Structure
NADP+
-
Mentha x piperita
NADPH
-
Mentha x piperita
Application (protein specific)
Application
Commentary
Organism
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
Mentha x piperita
Cloned(Commentary) (protein specific)
Commentary
Organism
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
Mentha x piperita
Cofactor (protein specific)
Cofactor
Commentary
Organism
Structure
NADP+
-
Mentha x piperita
NADPH
-
Mentha x piperita
Engineering (protein specific)
Amino acid exchange
Commentary
Organism
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
Mentha x piperita
Natural Substrates/ Products (Substrates) (protein specific)
Natural Substrates
Organism
Commentary (Nat. Sub.)
Natural Products
Commentary (Nat. Pro.)
Organism (Nat. Pro.)
Reversibility
(-)-menthone + NADPH + H+
Mentha x piperita
menthone reduction is the physiological reaction of enzyme MNMR
(+)-neomenthol + NADP+
-
-
r
Purification (Commentary) (protein specific)
Commentary
Organism
recombinant His6-tagged enzyme from Escherichia coli strain NiCO2(DE3) by nickel affinity chromatography and gel filtration
Mentha x piperita
Substrates and Products (Substrate) (protein specific)
Substrates
Commentary Substrates
Literature (Substrates)
Organism
Products
Commentary (Products)
Literature (Products)
Organism (Products)
Reversibility
(-)-menthone + NADPH + H+
-
739778
Mentha x piperita
(+)-neomenthol + NADP+
-
-
-
r
(-)-menthone + NADPH + H+
menthone reduction is the physiological reaction of enzyme MNMR
739778
Mentha x piperita
(+)-neomenthol + NADP+
-
-
-
r
(2R,5R)-isomenthone + NADPH + H+
-
739778
Mentha x piperita
(+)-neomenthol + NADP+
-
-
-
r
(2S,5R)-menthone + NADPH + H+
-
739778
Mentha x piperita
(+)-neomenthol + NADP+
-
-
-
r
additional information
enzyme MNMR has a preference for menthone over isomenthone
739778
Mentha x piperita
?
-
-
-
-
Temperature Optimum [C] (protein specific)
Temperature Optimum [C]
Temperature Optimum Maximum [C]
Commentary
Organism
30
-
assay at
Mentha x piperita
Turnover Number [1/s] (protein specific)
Turnover Number Minimum [1/s]
Turnover Number Maximum [1/s]
Substrate
Commentary
Organism
Structure
0.2
-
(2R,5R)-isomenthone
recombinant His6-tagged enzyme, pH 7.0, 30C
Mentha x piperita
0.96
-
(2S,5R)-menthone
recombinant His6-tagged enzyme, pH 7.0, 30C
Mentha x piperita
General Information
General Information
Commentary
Organism
metabolism
the enzyme is involved in neomenthol biosynthesis in the peppermint pathway, overview
Mentha x piperita
General Information (protein specific)
General Information
Commentary
Organism
metabolism
the enzyme is involved in neomenthol biosynthesis in the peppermint pathway, overview
Mentha x piperita
Other publictions for EC 1.1.1.208
No.
1st author
Pub Med
title
organims
journal
volume
pages
year
Activating Compound
Application
Cloned(Commentary)
Crystallization (Commentary)
Engineering
General Stability
Inhibitors
KM Value [mM]
Localization
Metals/Ions
Molecular Weight [Da]
Natural Substrates/ Products (Substrates)
Organic Solvent Stability
Organism
Oxidation Stability
Posttranslational Modification
Purification (Commentary)
Reaction
Renatured (Commentary)
Source Tissue
Specific Activity [micromol/min/mg]
Storage Stability
Substrates and Products (Substrate)
Subunits
Temperature Optimum [C]
Temperature Range [C]
Temperature Stability [C]
Turnover Number [1/s]
pH Optimum
pH Range
pH Stability
Cofactor
Ki Value [mM]
pI Value
IC50 Value
Activating Compound (protein specific)
Application (protein specific)
Cloned(Commentary) (protein specific)
Cofactor (protein specific)
Crystallization (Commentary) (protein specific)
Engineering (protein specific)
General Stability (protein specific)
IC50 Value (protein specific)
Inhibitors (protein specific)
Ki Value [mM] (protein specific)
KM Value [mM] (protein specific)
Localization (protein specific)
Metals/Ions (protein specific)
Molecular Weight [Da] (protein specific)
Natural Substrates/ Products (Substrates) (protein specific)
Organic Solvent Stability (protein specific)
Oxidation Stability (protein specific)
Posttranslational Modification (protein specific)
Purification (Commentary) (protein specific)
Renatured (Commentary) (protein specific)
Source Tissue (protein specific)
Specific Activity [micromol/min/mg] (protein specific)
Storage Stability (protein specific)
Substrates and Products (Substrate) (protein specific)
Subunits (protein specific)
Temperature Optimum [C] (protein specific)
Temperature Range [C] (protein specific)
Temperature Stability [C] (protein specific)
Turnover Number [1/s] (protein specific)
pH Optimum (protein specific)
pH Range (protein specific)
pH Stability (protein specific)
pI Value (protein specific)
Expression
General Information
General Information (protein specific)
Expression (protein specific)
KCat/KM [mM/s]
KCat/KM [mM/s] (protein specific)
739778
Toogood
Enzymatic menthol production: ...
Mentha x piperita
ACS Synth. Biol.
4
1112-1123
2015
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1
1
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1
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5
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1
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1
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726141
Ryden
Molecular cloning and characte ...
Artemisia annua
Plant Cell Physiol.
51
1219-1228
2010
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1
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2
2
689629
Choi
A role for a menthone reductas ...
Arabidopsis thaliana, Capsicum annuum
Plant Physiol.
148
383-401
2008
1
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2
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2
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4
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5
1
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3
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1
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670590
Davis
Monoterpene metabolism. Clonin ...
Mentha x piperita
Plant Physiol.
137
873-881
2005
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1
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4
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1
3
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3
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5
1
1
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1
1
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1
3
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5
1
1
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2
1
1
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347974
Kjonaas
Metabolism of monoterpenes: Co ...
Mentha x piperita
Plant Physiol.
69
1013-1017
1982
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-
-
-
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4
1
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1
1
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1
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1
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3
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3
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1
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347975
Croteau
Demonstration of the intercell ...
Mentha x piperita
Plant Physiol.
69
975-977
1982
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