KEGG   ENZYME: 1.14.14.143
Entry
EC 1.14.14.143              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 reduced flavin or flavoprotein as one donor, and incorporation of one atom of oxygen into the other donor
Sysname
(+)-pulegone,[reduced NADPH---hemoprotein reductase]:oxygen oxidoreductase (9-hydroxylating)
Reaction(IUBMB)
(+)-pulegone + [reduced NADPH---hemoprotein reductase] + O2 = (+)-menthofuran + [oxidized NADPH---hemoprotein reductase] + H2O [RN:R08923]
Reaction(KEGG)
R08923
Substrate
(+)-pulegone [CPD:C09893];
[reduced NADPH---hemoprotein reductase] [CPD:C03024];
O2 [CPD:C00007]
Product
(+)-menthofuran [CPD:C18025];
[oxidized NADPH---hemoprotein reductase] [CPD:C03161];
H2O [CPD:C00001]
Comment
A cytochrome P-450 (heme-thiolate) protein. 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 1.14.14.99, (S)-limonene 3-monooxygenase [1].
History
EC 1.14.14.143 created 2008 as EC 1.14.13.104, transferred 2018 to EC 1.14.14.143
Pathway
ec00902  Monoterpenoid biosynthesis
ec01110  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 390:279-86 (2001)
DOI:10.1006/abbi.2001.2378
  Sequence
[ag:AAL06397]
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 100:14481-6 (2003)
DOI:10.1073/pnas.2436325100
  Sequence
[ag:AAL06397]
Other DBs
ExplorEnz - The Enzyme Database: 1.14.14.143
IUBMB Enzyme Nomenclature: 1.14.14.143
ExPASy - ENZYME nomenclature database: 1.14.14.143
BRENDA, the Enzyme Database: 1.14.14.143

  All links  
Pathway (4)   
   KEGG PATHWAY (4)   
Chemical substance (6)   
   KEGG COMPOUND (6)   
Chemical reaction (2)   
   KEGG REACTION (1)   
   KEGG RCLASS (1)   
Gene (2)   
   KEGG ORTHOLOGY (1)   
   KEGG GENES (1)   
Protein sequence (5)   
   UniProt (4)   
   SWISS-PROT (1)   
Protein domain (5)   
   InterPro (5)   
All databases (24)   

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