Information on EC 1.14.13.104 - (+)-menthofuran synthase

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The expected taxonomic range for this enzyme is: Mentha

EC NUMBER
COMMENTARY hide
1.14.13.104
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RECOMMENDED NAME
GeneOntology No.
(+)-menthofuran synthase
REACTION
REACTION DIAGRAM
COMMENTARY hide
ORGANISM
UNIPROT
LITERATURE
(+)-pulegone + NADPH + H+ + O2 = (+)-menthofuran + NADP+ + H2O
show the reaction diagram
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PATHWAY
BRENDA Link
KEGG Link
MetaCyc Link
Biosynthesis of secondary metabolites
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menthol biosynthesis
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Monoterpenoid biosynthesis
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SYSTEMATIC NAME
IUBMB Comments
(+)-pulegone,NADPH:oxygen oxidoreductase (9-hydroxylating)
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].
ORGANISM
COMMENTARY hide
LITERATURE
UNIPROT
SEQUENCE DB
SOURCE
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Manually annotated by BRENDA team
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UniProt
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
(+)-pulegone + NADPH + H+ + O2
(+)-menthofuran + NADP+ + H2O
show the reaction diagram
additional information
?
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regulation of pulegone metabolism involves menthofuran, the flux of (+)-pulegone through pulegone reductase correlates negatively with the essential oil content of menthofuran, such that menthofuran, and pulegone increase, or decrease, in concert, overview, although (+)-menthofuran does not inhibit (+)-pulegone reductase activity, stem feeding with menthofuran selectively decreases enzyme transcript levels in immature leaves, thereby accounting for decreased reductase activity and increased pulegone content, overview
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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
(+)-pulegone + NADPH + H+ + O2
(+)-menthofuran + NADP+ + H2O
show the reaction diagram
additional information
?
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regulation of pulegone metabolism involves menthofuran, the flux of (+)-pulegone through pulegone reductase correlates negatively with the essential oil content of menthofuran, such that menthofuran, and pulegone increase, or decrease, in concert, overview, although (+)-menthofuran does not inhibit (+)-pulegone reductase activity, stem feeding with menthofuran selectively decreases enzyme transcript levels in immature leaves, thereby accounting for decreased reductase activity and increased pulegone content, overview
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COFACTOR
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
cytochrome P450
METALS and IONS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
pH OPTIMUM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
TEMPERATURE OPTIMUM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
LOCALIZATION
ORGANISM
UNIPROT
COMMENTARY hide
GeneOntology No.
LITERATURE
SOURCE
SUBUNITS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
?
x * 55360, sequence calculation
Cloned/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
DNA and amino acid sequence determinationand analysis, functional expression in Saccharomyces cerevisiae strains WAT11U and WAT21U, which constitutively express two different isoforms of the Arabidposis thaliana NADPH-cytochrome P450 reductase, and in Escherichia coli strain JM109
expression of a homologous antisense version of the menthofuran synthase cDNA, both driven by the CaMV 35S promoter, in Mentha x piperita plants using Agrobacterium tumefaciens strain EHA105 transfection method
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gene mfs, expression under control of the CaMV 35S promoter in transformed peppermint plants
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ENGINEERING
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
additional information