Information on EC 1.3.1.82 - (-)-isopiperitenone reductase

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The expected taxonomic range for this enzyme is: Mentha

EC NUMBER
COMMENTARY hide
1.3.1.82
-
RECOMMENDED NAME
GeneOntology No.
(-)-isopiperitenone reductase
REACTION
REACTION DIAGRAM
COMMENTARY hide
ORGANISM
UNIPROT
LITERATURE
(+)-cis-isopulegone + NADP+ = (-)-isopiperitenone + NADPH + H+
show the reaction diagram
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-
-
-
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
(+)-cis-isopulegone:NADP+ oxidoreductase
The reaction occurs in the opposite direction to that shown above. The enzyme participates in the menthol-biosynthesis pathway of Mentha plants. (+)-Pulegone, (+)-cis-isopulegone and (-)-menthone are not substrates. The enzyme has a preference for NADPH as the reductant, with NADH being a poor substitute [2]. The enzyme is highly regioselective for the reduction of the endocyclic 1,2-double bond, and is stereoselective, producing only the 1R-configured product. It is a member of the short-chain dehydrogenase/reductase superfamily.
CAS REGISTRY NUMBER
COMMENTARY hide
138066-94-1
-
ORGANISM
COMMENTARY hide
LITERATURE
UNIPROT
SEQUENCE DB
SOURCE
-
-
-
Manually annotated by BRENDA team
SUBSTRATE
PRODUCT                       
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate) hide
LITERATURE
(Substrate)
COMMENTARY
(Product) hide
LITERATURE
(Product)
Reversibility
r=reversible
ir=irreversible
?=not specified
(-)-isopiperitenone + NADPH + H+
(+)-cis-isopulegone + NADP+
show the reaction diagram
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
(-)-isopiperitenone + NADPH + H+
(+)-cis-isopulegone + NADP+
show the reaction diagram
COFACTOR
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
NADPH
KM VALUE [mM]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.001
(-)-isopiperitenone
-
pH 5.5, recombinant enzyme
0.0022
NADPH
-
pH 5.5, recombinant enzyme
TURNOVER NUMBER [1/s]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
1.3
(-)-isopiperitenone
pH OPTIMUM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
5.5
-
wild-type enzyme
6.5
-
truncated mutant enzyme
pH RANGE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
4.5 - 7.5
-
50% of maximal activity within this range, wild-type enzyme
5 - 8
-
50% of maximal activity within this range, deletion mutant enzyme
SOURCE TISSUE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
SOURCE
LOCALIZATION
ORGANISM
UNIPROT
COMMENTARY hide
GeneOntology No.
LITERATURE
SOURCE
PDB
SCOP
CATH
ORGANISM
UNIPROT
MOLECULAR WEIGHT
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
60000
-
about, gel filtration
SUBUNITS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
dimer
-
2 * 34409, sequence calculation, 2 * 38000, SDS-PAGE
Purification/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
recombinant wild-type enzyme from Escherichia coli strain BL21(DE3) to over 60% homogeneity, and to over 90% purity for the truncated mutant enzyme
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Cloned/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
DNA and amino acid sequence determination and analysis, functional expression of wild-type enzyme in Escherichia coli strain BL21(DE3), expression of a mutant cloning artifact that has a seven residue deletion at the C-terminus and bores an additional 33 vector-derived residues
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