KEGG   ENZYME: 1.14.14.143Help
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
BRITE hierarchy
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)
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
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
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

DBGET integrated database retrieval system