Literature summary for 1.3.1.82 extracted from

  • Lygidakis, A.; Karuppiah, V.; Hoeven, R.; Ni Cheallaigh, A.; Leys, D.; Gardiner, J.M.; Toogood, H.S.; Scrutton, N.S.
    Pinpointing a mechanistic switch between ketoreduction and Ene reduction in short-chain dehydrogenases/reductases (2016), Angew. Chem. Int. Ed. Engl., 55, 9596-9600 .
    View publication on PubMedView publication on EuropePMC

Crystallization (Commentary)

Crystallization (Comment) Organism
enzyme IPR in apoform and in complex with NADP+, alkene 3-methyl-6-(prop-1-en-2-yl)cyclohex-2-en-1-one, and beta-cyclocitral, X-ray diffraction structure determination and analysis using using SalR crystal structure, PDB ID 3O26, at 1.2 and 1.7 A resolution, respectively, via molecular replacement, PDB ID 5LCX Mentha x piperita

Engineering

Protein Variants Comment Organism
E238Y site-directed mutagenesis, the mutant shows highly altered substrate specificity compared to the wild-type enzyme Mentha x piperita

Natural Substrates/ Products (Substrates)

Natural Substrates Organism Comment (Nat. Sub.) Natural Products Comment (Nat. Pro.) Rev. Reac.
additional information Mentha x piperita compound analysis by GS-MS. 3-methyl-6-(prop-1-en-2-yl)cyclohex-2-en-1-one is a poor substrate for enzyme mutant E238Y. Substrate specificity of wild-type and mutant enzymes and ligand binding structure analysis, overview ?
-
?
(2S,5R)-5-methyl-2-(propan-2-yl)cyclohexan-1-one + NADP+ Mentha x piperita reaction of enzyme mutant E238Y, not of the wild-type enzyme (2S,5R)-5-methyl-2-(propan-2-yl)cyclohexan-1-ol + (1S,2R,5R)-5-methyl-2-(propan-2-yl)cyclohexan-1-ol + NADPH + H+
-
?
2,6,6-trimethyl-4-oxocyclohex-2-ene-1-carbaldehyde + NADP+ Mentha x piperita
-
2,2,6-trimethyl-4-oxocyclohexane-1-carbaldehyde + NADPH + H+
-
?
3,5,5-trimethyl-4-(propan-2-yl)cyclohex-2-en-1-one + NADP+ Mentha x piperita
-
3,3,5-trimethyl-4-(propan-2-yl)cyclohexan-1-one + NADPH + H+
-
?
3,5,5-trimethylcyclohex-2-en-1-one + NADP+ Mentha x piperita
-
3,3,5-trimethylcyclohexan-1-one + NADPH + H+
-
?
3,5-dimethylcyclohex-2-en-1-one + NADP+ Mentha x piperita
-
3,5-dimethylcyclohexan-1-one + NADPH + H+
-
?
3-methyl-6-(prop-1-en-2-yl)cyclohex-2-en-1-one + NADP+ Mentha x piperita
-
5-methyl-2-(prop-1-en-2-yl)cyclohexan-1-one + NADPH + H+
-
?
3-methyl-6-(propan-2-yl)cyclohex-2-en-1-one + NADP+ Mentha x piperita
-
5-methyl-2-(propan-2-yl)cyclohexan-1-one + NADPH + H+
-
?

Organism

Organism UniProt Comment Textmining
Mentha x piperita Q6WAU1
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-

Source Tissue

Source Tissue Comment Organism Textmining

Substrates and Products (Substrate)

Substrates Comment Substrates Organism Products Comment (Products) Rev. Reac.
additional information compound analysis by GS-MS. 3-methyl-6-(prop-1-en-2-yl)cyclohex-2-en-1-one is a poor substrate for enzyme mutant E238Y. Substrate specificity of wild-type and mutant enzymes and ligand binding structure analysis, overview Mentha x piperita ?
-
?
(2S,5R)-5-methyl-2-(propan-2-yl)cyclohexan-1-one + NADP+ reaction of enzyme mutant E238Y, not of the wild-type enzyme Mentha x piperita (2S,5R)-5-methyl-2-(propan-2-yl)cyclohexan-1-ol + (1S,2R,5R)-5-methyl-2-(propan-2-yl)cyclohexan-1-ol + NADPH + H+
-
?
2,6,6-trimethyl-4-oxocyclohex-2-ene-1-carbaldehyde + NADP+
-
Mentha x piperita 2,2,6-trimethyl-4-oxocyclohexane-1-carbaldehyde + NADPH + H+
-
?
3,5,5-trimethyl-4-(propan-2-yl)cyclohex-2-en-1-one + NADP+
-
Mentha x piperita 3,3,5-trimethyl-4-(propan-2-yl)cyclohexan-1-one + NADPH + H+
-
?
3,5,5-trimethylcyclohex-2-en-1-one + NADP+
-
Mentha x piperita 3,3,5-trimethylcyclohexan-1-one + NADPH + H+
-
?
3,5-dimethylcyclohex-2-en-1-one + NADP+
-
Mentha x piperita 3,5-dimethylcyclohexan-1-one + NADPH + H+
-
?
3-methyl-6-(prop-1-en-2-yl)cyclohex-2-en-1-one + NADP+
-
Mentha x piperita 5-methyl-2-(prop-1-en-2-yl)cyclohexan-1-one + NADPH + H+
-
?
3-methyl-6-(propan-2-yl)cyclohex-2-en-1-one + NADP+
-
Mentha x piperita 5-methyl-2-(propan-2-yl)cyclohexan-1-one + NADPH + H+
-
?

Subunits

Subunits Comment Organism
More enzyme three-dimensional structure analysis, overview Mentha x piperita

Synonyms

Synonyms Comment Organism
isopiperitenone reductase
-
Mentha x piperita
IPR
-
Mentha x piperita

Temperature Optimum [°C]

Temperature Optimum [°C] Temperature Optimum Maximum [°C] Comment Organism
25
-
assay at Mentha x piperita

pH Optimum

pH Optimum Minimum pH Optimum Maximum Comment Organism
6
-
assay at Mentha x piperita

Cofactor

Cofactor Comment Organism Structure
NADP+
-
Mentha x piperita

General Information

General Information Comment Organism
evolution the enzyme belongs to the short-chain dehydrogenases/reductases SDR superfamily. A sequence alignment of the three ketoreductases MMR, MNMR, and salutaridine reductase (45-49% homology to Mentha enzymes) from Papaver somniferum with Mentha pipertita enzyme IPR shows each enzyme contains typical SDR-like motifs, such as those involved in central beta-sheet stabilization, and a TGxxxGhG motif Mentha x piperita
additional information the catalytic acid residue in enzyme IPR is Glu238, analysis of its role in reaction mechanism Mentha x piperita