KEGG   ENZYME: 1.3.1.82Help
Entry
EC 1.3.1.82                 Enzyme                                 

Name
(-)-isopiperitenone reductase
Class
Oxidoreductases;
Acting on the CH-CH group of donors;
With NAD+ or NADP+ as acceptor
BRITE hierarchy
Sysname
(+)-cis-isopulegone:NADP+ oxidoreductase
Reaction(IUBMB)
(+)-cis-isopulegone + NADP+ = (-)-isopiperitenone + NADPH + H+ [RN:R06417]
Reaction(KEGG)
Substrate
(+)-cis-isopulegone [CPD:C11951];
NADP+ [CPD:C00006]
Product
(-)-isopiperitenone [CPD:C02485];
NADPH [CPD:C00005];
H+ [CPD:C00080]
Comment
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.
History
EC 1.3.1.82 created 2008
Pathway
Monoterpenoid biosynthesis
Biosynthesis of secondary metabolites
Orthology
K15091  
(-)-isopiperitenone reductase
Reference
1  [PMID:3755881]
  Authors
Croteau R, Venkatachalam KV.
  Title
Metabolism of monoterpenes: demonstration that (+)-cis-isopulegone, not piperitenone, is the key intermediate in the conversion of (-)-isopiperitenone to (+)-pulegone in peppermint (Mentha piperita).
  Journal
Arch. Biochem. Biophys. 249 (1986) 306-15.
Reference
2  [PMID:13679086]
  Authors
Ringer KL, McConkey ME, Davis EM, Rushing GW, Croteau R.
  Title
Monoterpene double-bond reductases of the (-)-menthol biosynthetic pathway: isolation and characterization of cDNAs encoding (-)-isopiperitenone reductase and (+)-pulegone reductase of peppermint.
  Journal
Arch. Biochem. Biophys. 418 (2003) 80-92.
  Sequence
Other DBs
ExplorEnz - The Enzyme Database: 
IUBMB Enzyme Nomenclature: 
ExPASy - ENZYME nomenclature database: 
BRENDA, the Enzyme Database: 

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