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  • Toogood, H.; Cheallaigh, A.; Tait, S.; Mansell, D.; Jervis, A.; Lygidakis, A.; Humphreys, L.; Takano, E.; Gardiner, J.; Scrutton, N.
    Enzymatic menthol production: one-pot approach using engineered Escherichia coli (2015), ACS Synth. Biol., 4, 1112-1123.
    View publication on PubMed

Application

EC Number Application Comment Organism
1.1.1.207 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 Mentha x piperita
1.1.1.208 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)

EC Number Cloned (Comment) Organism
1.1.1.207 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 Mentha x piperita
1.1.1.208 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

Protein Variants

EC Number Protein Variants Comment Organism
1.1.1.207 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
1.1.1.208 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)

EC Number Natural Substrates Organism Comment (Nat. Sub.) Natural Products Comment (Nat. Pro.) Rev. Reac.
1.1.1.207 (-)-menthone + NADPH + H+ Mentha x piperita menthone reduction is the physiological reaction of enzyme MMR (-)-menthol + NADP+
-
 r
1.1.1.208 (-)-menthone + NADPH + H+ Mentha x piperita menthone reduction is the physiological reaction of enzyme MNMR (+)-neomenthol + NADP+
-
 r

Organism

EC Number Organism UniProt Comment Textmining
1.1.1.207 Mentha x piperita Q5CAF4
-
-
1.1.1.208 Mentha x piperita Q06ZW2
-
-

Purification (Commentary)

EC Number Purification (Comment) Organism
1.1.1.207 recombinant His6-tagged enzyme from Escherichia coli strain NiCO2(DE3) by nickel affinity chromatography and gel filtration Mentha x piperita
1.1.1.208 recombinant His6-tagged enzyme from Escherichia coli strain NiCO2(DE3) by nickel affinity chromatography and gel filtration Mentha x piperita

Substrates and Products (Substrate)

EC Number Substrates Comment Substrates Organism Products Comment (Products) Rev. Reac.
1.1.1.207 (-)-menthone + NADPH + H+
-
 Mentha x piperita (-)-menthol + NADP+
-
 r
1.1.1.207 (-)-menthone + NADPH + H+ menthone reduction is the physiological reaction of enzyme MMR Mentha x piperita (-)-menthol + NADP+
-
 r
1.1.1.207 (2R,5R)-isomenthone + NADPH + H+
-
 Mentha x piperita (-)-menthol + NADP+
-
 r
1.1.1.207 (2S,5R)-menthone + NADPH + H+
-
 Mentha x piperita (-)-menthol + NADP+
-
 r
1.1.1.207 additional information enzyme MMR has a preference for menthol over neomenthol from menthone and neoisomenthol over isomenthol with isomenthone Mentha x piperita ?
-
 ?
1.1.1.208 (-)-menthone + NADPH + H+
-
 Mentha x piperita (+)-neomenthol + NADP+
-
 r
1.1.1.208 (-)-menthone + NADPH + H+ menthone reduction is the physiological reaction of enzyme MNMR Mentha x piperita (+)-neomenthol + NADP+
-
 r
1.1.1.208 (2R,5R)-isomenthone + NADPH + H+
-
 Mentha x piperita (+)-neomenthol + NADP+
-
 r
1.1.1.208 (2S,5R)-menthone + NADPH + H+
-
 Mentha x piperita (+)-neomenthol + NADP+
-
 r
1.1.1.208 additional information enzyme MNMR has a preference for menthone over isomenthone Mentha x piperita ?
-
 ?

Synonyms

EC Number Synonyms Comment Organism
1.1.1.207 menthone:(-)-menthol reductase
-
 Mentha x piperita
1.1.1.207 MMR
-
 Mentha x piperita
1.1.1.208 (-)-menthone:(+)-neomenthol reductase UniProt Mentha x piperita
1.1.1.208 menthone:(+)-neomenthol reductase
-
 Mentha x piperita
1.1.1.208 MNMR
-
 Mentha x piperita

Temperature Optimum [°C]

EC Number Temperature Optimum [°C] Temperature Optimum Maximum [°C] Comment Organism
1.1.1.207 30
-
 assay at Mentha x piperita
1.1.1.208 30
-
 assay at Mentha x piperita

Turnover Number [1/s]

EC Number Turnover Number Minimum [1/s] Turnover Number Maximum [1/s] Substrate Comment Organism Structure
1.1.1.207 1.63
-
 (2S,5R)-menthone recombinant His6-tagged enzyme, pH 7.0, 30°C Mentha x piperita
1.1.1.207 2
-
 (2R,5R)-isomenthone recombinant His6-tagged enzyme, pH 7.0, 30°C Mentha x piperita
1.1.1.208 0.2
-
 (2R,5R)-isomenthone recombinant His6-tagged enzyme, pH 7.0, 30°C Mentha x piperita
1.1.1.208 0.96
-
 (2S,5R)-menthone recombinant His6-tagged enzyme, pH 7.0, 30°C Mentha x piperita

pH Optimum

EC Number pH Optimum Minimum pH Optimum Maximum Comment Organism
1.1.1.207 7
-
 assay at Mentha x piperita

Cofactor

EC Number Cofactor Comment Organism Structure
1.1.1.207 NADP+
-
 Mentha x piperita
1.1.1.207 NADPH
-
 Mentha x piperita
1.1.1.208 NADP+
-
 Mentha x piperita
1.1.1.208 NADPH
-
 Mentha x piperita

General Information

EC Number General Information Comment Organism
1.1.1.207 metabolism the enzyme is involved in menthol biosynthesis in the peppermint pathway, overview Mentha x piperita
1.1.1.208 metabolism the enzyme is involved in neomenthol biosynthesis in the peppermint pathway, overview Mentha x piperita