KEGG   ENZYME: 1.14.13.104Help
Entry
EC 1.14.13.104              Enzyme                                 

Name
(+)-menthofuran synthase;
menthofuran synthase;
(+)-pulegone 9-hydroxylase;
(+)-MFS;
cytochrome P450 menthofuran synthase
Class
Oxidoreductases;
Acting on paired donors, with incorporation or reduction of molecular oxygen;
With NADH or NADPH as one donor, and incorporation of one atom of oxygen into the other donor
BRITE hierarchy
Sysname
(+)-pulegone,NADPH:oxygen oxidoreductase (9-hydroxylating)
Reaction(IUBMB)
(+)-pulegone + NADPH + H+ + O2 = (+)-menthofuran + NADP+ + H2O [RN:R08923]
Reaction(KEGG)
Substrate
(+)-pulegone [CPD:C09893];
NADPH [CPD:C00005];
H+ [CPD:C00080];
O2 [CPD:C00007]
Product
(+)-menthofuran [CPD:C18025];
NADP+ [CPD:C00006];
H2O [CPD:C00001]
Comment
A heme-thiolate protein (P-450). The conversion of substrate into product involves the hydroxylation of the syn-methyl (C9), intramolecular cyclization to the hemiketal and dehydration to the furan [1]. This is the second cytochrome P-450-mediated step of monoterpene metabolism in peppermint, with the other step being catalysed by EC 1.14.13.47, (S)-limonene 3-monooxygenase [1].
History
EC 1.14.13.104 created 2008
Pathway
Monoterpenoid biosynthesis
Biosynthesis of secondary metabolites
Orthology
K15093  
(+)-menthofuran synthase
Reference
1  [PMID:11396930]
  Authors
Bertea CM, Schalk M, Karp F, Maffei M, Croteau R.
  Title
Demonstration that menthofuran synthase of mint (Mentha) is a cytochrome P450 monooxygenase: cloning, functional expression, and characterization of the responsible gene.
  Journal
Arch. Biochem. Biophys. 390 (2001) 279-86.
  Organism
Mentha x piperita
  Sequence
[up:Q947B7]
Reference
2  [PMID:14623962]
  Authors
Mahmoud SS, Croteau RB.
  Title
Menthofuran regulates essential oil biosynthesis in peppermint by controlling a downstream monoterpene reductase.
  Journal
Proc. Natl. Acad. Sci. U. S. A. 100 (2003) 14481-6.
  Organism
Mentha x piperita
  Sequence
[up:Q947B7]
Other DBs
ExplorEnz - The Enzyme Database: 
IUBMB Enzyme Nomenclature: 
ExPASy - ENZYME nomenclature database: 
BRENDA, the Enzyme Database: 

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